sailboat tour chicago

Opening for the Season: May 17th, 2024! Click to book your next sail on board Tall Ship Windy!

Tall Ship Windy

All Sails in Chicago, IL

Browse our sails below and book your Chicago Sailing Adventure today!

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  • Hour Glass 75 minutes

Chicago Skyline Sunset Sail

For the best Chicago sunset, visitors and residents alike, join us aboard 148′ Tall Ship Windy – the official ambassador for the City of Chicago. Departing Navy Pier at 7pm daily, you will enjoy a spectacular sailing cruise and enjoy the breathtaking moments as the sun sets gently behind the Chicago Skyline.

  • Hour Glass 2 Hours

Monday Night Blues Summer Concert Series

Kick-off your week and join us for a 2-hour concert sail from 7pm-9pm every Monday this summer. We’ll help you chase your Monday BLUES away aboard the 148 foot Tall Ship Windy as you enjoy the breathtaking views of Chicago from the waters of Lake Michigan accompanied by the sweet sounds of the blues.

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Chicago Skyline Sail Aboard 148' Tall Ship Windy

Explore Chicago’s scenic shores with a relaxing sail around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views and discover the Windy City from the water. Select from Pirates and Maritime Stories at 1pm, Architectural and Skyline Tours at 3pm and 5pm and  Sunset and Skyline Sails at 7pm.

  • Great for Children!
  • Hour Glass 90 minutes

Educational Sail: Tall Ship Discovery Sail

History comes alive on this exciting educational adventure for curious minds of all ages. Experience a hands-on sailing trip aboard Windy led by our crew-educators.

  • Every night at 5pm!

Happy Arr-our Chicago Architecture and Skyline Sail

Enjoy onboard happy hour drink specials every night at 5pm and experience breathtaking views of the Chicago skyline from the water! It’s the perfect way to end your workday or kick off your weekend plans. Learn about the people, plans and persistence that shaped Chicago’s most famous sights and join us on the main deck to enjoy the lively narration.

Chicago’s Famous Friday Night Pirates Pub Sail

Sail into the night and embark on a two-hour party sail; join us for Chicago’s only Pirates Pub. Sail onboard a 148-foot Tall Ship in the Windy City! This is an event you will not want to miss. Enjoy an onboard DJ and the wind in your hair as you dance the night away with the mesmerizing Chicago skyline as your backdrop. Sing along to traditional pirate tunes and your favorite party anthems while soaking in the breathtaking sights of Lake Michigan.

Fireworks Cruise! Aboard Tall Ship Windy!

Watching Fireworks from Navy Pier has become a Chicago tradition and there is no better seat in the house to watch the show than sailing aboard 148′ Tall Ship Windy – the Official Flagship of the City of Chicago! Order a cold drink from our bar and enjoy a thrilling fireworks performance as you sail along the stunning and iconic Chicago skyline during this special event sail.

  • VIP Event - Limited Availability
  • Hour Glass 3 hours

Chicago Air and Water Show Aboard Famous Tall Ship Windy

The thrill of the Chicago Air & Water Show returns to the Lake Michigan lakefront this year on Saturday, August 10, and Sunday, August 11, 2024. Join us onboard Tall Ship Windy to enjoy 3 hours of the show from the water.

Fireworks Sails

Special sails.

Are you looking for a relaxing sail along the Lake Michigan lakefront? Are you interested in an educational tour featuring stories from Chicago’s unique history? Or maybe you would prefer to enjoy a drink or two while watching a thrilling fireworks display over the stunning Chicago skyline? Let Tall Ship Windy be your guide!

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Nebula- A Chicago Sailboat

The Chicago sailboat Nebula is a 40-foot sloop-rig Beneteau, providing guests with comfort during their excursions. The nebula is the perfect cruising sailboat for enjoying the Chicago Lakefront as it has several exquisite features that enhance the sailing experience.

Nebula Bareboat Charter Boat with Windy City Sailing

Topside of Nebula Chicago Sailboat

The Nebula accommodates up to ten (10) guests and is ideal for relaxing on the Chicago Lakefront.  The custom-made cushions provide comfort and relaxation during a leisurely cruise. Also, the large bimini (sunshade) provides protection from the sun on those hot summer days.

Your party can easily jump into the lake and climb back aboard using the convenient swim ladder. As an added luxury, you can take a hot shower on the swim deck when you've finished swimming.

sailboat tour chicago

FIVE STAR RATINGS ON TRIP ADVISOR AND GOOGLE

WINDY CITY SAILING HAS PROUDLY BEEN OFFERING EXCEPTIONAL SERVICE FOR TWO DECADES AND WE HAVE THE SATISFIED RETURNING CUSTOMERS TO PROVE IT!

Interior Image of Nebula Bareboat Charter Yacht

Nebula's Main Cabin- Chicago Sailboat

The Nebula’s main cabin is stocked with amenities ensuring guests will fully enjoy their Chicago sailboat charter. Furthermore, ample natural light and ventilation enhance the comfort of the cabin.

Crafted in cherry-finish woodwork;  guests will find everything they may need in here.  Most noteworthy, the 20” flat screen TV/monitor, Bluetooth stereo, and air conditioning provide an enjoyable onboard experience.

Interior Image of Nebula Bareboat Charter with Windy City Sailing

Nebula's Galley- Chicago Sailboat

In Nebula’s custom-designed galley, guests have the use of the kitchen amenities they find in their own homes. Most useful, the large freezer stocked with ice, microwave, and double bin sink are all easily accessible onboard.  Likewise, glasses, plates, utensils, wine/bottle openers, and cutting boards are provided.

Sailing Questions

As you plan to set sail on the mesmerizing Lake Michigan and explore the scenic shoreline of Chicago, you may have inquiries about the weather, safety precautions, rules and regulations, required sailing equipment, licensing needs, recommended routes, local marine life, and nearby amenities. This FAQ is intended to address all these queries and any others that could enhance your sailing experience in the Chicago Harbor. Let's embark on this exciting adventure!

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[email protected]

sailboat tour chicago

CHICAGO SAILBOAT & YACHT RENTALS

When you rent a boat from chicago sailboat & yacht charters, we provide the best variety, service, and value for any charter or rental boat experience you desire., chicago's top boat rental.

sailboat tour chicago

Whether you are looking for a romantic sailing trip for two, a sailboat for up to 11 people, power boat rental for up to 12 people, or a party boat rental for up to 36, Chicago Sailboat Charters & Rentals has the perfect charter for you, every day of the week!

HOW TO BOOK YOUR BOAT CHARTER ONLINE

Step 1: Use our online booking platform (click HERE ) to select your date and view charter availability.

Step 2: Once you select your charter, reserve and pay directly online in less than 60 seconds.

Step 3: After booking, refer to your confirmation email for instructions on how to book a captain.

WHY CHICAGO SAILBOAT CHARTERS?

Chicago Sailboat Charters offers Chicago's largest variety of captained charters for sailboats, yachts, and spacious boats, accommodating groups of 1 to 36 people. Enjoy daytime sailing, sunset cruises, swimming and sunbathing sails, or even witness the spectacular Navy Pier fireworks from our boats.

OUR SAILBOAT & YACHT RENTALS ARE PERFECT FOR...

Swimming & playpen, navy pier fireworks, chicago river cruises, celebration events, corporate outings.

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400 West Belmont Harbor Drive, Chicago, IL 60657

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chicago boat tours

The 15 best boat tours in Chicago

See the skyline from dazzling new vantage points aboard one of the best boat tours in Chicago

Sure, walks along Michigan Avenue and State Street are nice and rooftop bars offer plenty of pretty sights – but the best way to see downtown Chicago is from the water. Both the Chicago River and Lake Michigan offer unparalleled vantage points for taking in the city’s world-famous architecture and the breathtaking Chicago skyline , with many of the tours providing unique insights into the city’s culture and history.

From architecture tours and history lessons to  straightforward sightseeing affairs , romantic excursions and pirate-themed family fun, there's a Chicago cruise for every groove. Below we’ve got the essential list of the city’s finest waterborne tours, including tall-mast ships and glitzy speed boats. Bon voyage!  

RECOMMENDED: Find more to explore with the best things to do in Chicago Plan your trip with the  best hotels in Chicago

Who makes the cut? While we might not stay in and review every hotel featured, we've based our list on our expert knowledge of the destination covered, editorial reviews, user reviews, hotel amenities and in-depth research to find you the best stays. This article includes affiliate links. These links have no influence on our editorial content. For more information, see our   affiliate   guidelines .

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Best Chicago boat tours

1.5-Hour Guided Architecture River Cruise

1.  1.5-Hour Guided Architecture River Cruise

Departing from Navy Pier's Polk Bros Park or the northeast corner of the Michigan Avenue Bridge, this 60-minute trip packs in all of the architectural sights that visitors want to see. Tour guides highlight more than 40 towering Chicago landmarks, including the Tribune Tower, the Wrigley Building, and Marina City (a.k.a. "The Corncobs" or " The Wilco Building "). 

Don't miss:  Locally sourced food and drink from the boat bar.  

Seadog River and Lake Architectural Tour

2.  Seadog River and Lake Architectural Tour

There are few more iconic Chicago sights than seeing the bright yellow Seadog speeding around town. Combining speed and sightseeing, Seadog’s architecture tour whizzes guests past the likes of the Willis Tower and Lyric Opera, all while arming you with an impressive load of facts about the Windy City. And after this blustery 75-minute tour has finished traversing the Chicago River, it ends with a thrilling whizz across Lake Michigan, past Museum Campus, and Grant Park. This one departs from Seadog’s dock at Navy Pier throughout the summer months.

Don't miss:  Local beer, spirits and Garrett's Popcorn at the boat bar.

Wendella: Chicago's Original Family-Friendly Architecture Tour

3.  Wendella: Chicago's Original Family-Friendly Architecture Tour

If you're weighing your options, Wendella's architecture tour (which it claims is Chicago's original ) is another way to explore all of the beautiful structures that line the river. Over the course of the 90-minute tour, you'll navigate all three branches of the Chicago River, while your guide fills you in on the stories behind some of the skyline's most prominent edifices. This tour departs from the Wendella Dock, located at the northwest corner of the Michigan Avenue Bridge at the foot of the Wrigley Building.

Don't miss: Live commentary from the tour guide, with material to entertain the whole family. 

1.5-Hour Romantic Sunset Cruise

4.  1.5-Hour Romantic Sunset Cruise

How do you end the perfect day of sightseeing? With the perfect sunset, obvs. Setting off from Wendella Dock (at the northwest corner of the Michigan Avenue Bridge at the foot of the Wrigley Building), this 90-minute cruise will breeze along Lake Michigan as the glint of the sun on Chicago's skyscrapers is replaced by twinkling city lights. 

Don't miss: Toasting to the end of the day with wine, local beer and hand-crafted cocktails.

Tall Ship Windy Architecture & Skyline Sailing Tour

5.  Tall Ship Windy Architecture & Skyline Sailing Tour

Let the wind carry you to stunning views of the city from aboard the Tall Ship Windy, a four-masted, 148-foot topsail schooner. The 75-minute trip cruise brings guests on a scenic route running along the Lake Michigan shoreline, where you can take in lovely skyline vistas and glimpses of the sunset. Head to the onboard bar to find snacks and drinks for sale. 

Don't miss:  Bring the kids for the special pirate-themed cruise, featuring  tales of swashbuckling  on the Great Lakes.  

Seadog Speedboat Tour

6.  Seadog Speedboat Tour

If you balk at the idea of traipsing around museums and galleries all day with just your legs for locomotion, this whistle-stop boat ride is the tour for you. See every worthy Chicago landmark in 30 minutes on Seadog’s speedboat, which can sometimes feel like a floating rollercoaster. Launching from Navy Pier, the captain will efficiently guide you (with a running commentary) around Lake Michigan, past Museum Campus, Magnificent Mile, Grant Park, and more.

Don't miss: Upgrade to the Extreme Thrill Ride, which includes full 360° spins and more. 

Lake Michigan Skyline Sightseeing Cruise

7.  Lake Michigan Skyline Sightseeing Cruise

Want to see Chicago from the water but don't have much time to spare? You can peep the skyline in just 30 minutes on Shoreline's Classic Lake Tour, which departs from Navy Pier and boasts some of the best views you'll find on Lake Michigan. The commentary on the city's architecture and history is pre-recorded, so you won't miss out on any information because your guide ran out of time (and if you've heard it before, you can sit back and enjoy those sweet, sweet sights).

Don't miss: Proceeding straight to the boarding line with a barcode that lets you skip the ticket office. 

Lake Michigan Gourmet Dinner Cruise

8.  Lake Michigan Gourmet Dinner Cruise

Enjoy a three-course gourmet dinner on the water in the Odyssey Chicago, where you can enjoy breathtaking views of the skyline surrounding you. Departing from Navy Pier, this cruise includes a dinner with freshly prepared entrées, mains, and desserts. The 2.5 or 3-hour ride takes you around Lake Michigan, with a cash bar to keep the drinks flowing throughout your meal.

Don't miss: The live DJ set and unlimited tea and coffee.

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9.  Chicago's Lake Michigan Kayak Tour

If you want to couple a workout with your sightseeing, consider touring Lake Michigan by kayak. The rental lasts one hour and if you've never kayaked before, don't worry – tandem kayaks are available for less experienced guests. The meeting point is at Ohio Street Beach and you'll be provided with a life jacket on arrival before paddling out onto Chicago's most incredible river view.

Don't miss: Take a break along the urban beachfront, with the chance to also rent stand-up paddle boards.  

Lake Michigan Buffet Brunch Cruise

10.  Lake Michigan Buffet Brunch Cruise

If you're looking for dinner with a view, you could do worse than watching the sunset against the skyline aboard this 2.5 or 3-hour Lake Michigan brunch, lunch, or dinner cruise. Grab a group of friends and book a table – ideally one with a window-facing view—for a buffet-style meal before making your way to the dancefloor for an evening of DJ-curated music. Unlimited coffee, tea, and water will be on hand.

Don't miss: Creative signature cocktails at the bar. 

Lake Michigan Odyssey Gourmet Lunch Cruise

11.  Lake Michigan Odyssey Gourmet Lunch Cruise

Why settle for lunch at a land-bound restaurant when you could eat your meal on Lake Michigan? The Odyssey's lunch cruise includes a three-course meal and all the coffee, hot tea, iced tea and water you can drink. Visit the cash bar to buy wine, beer and cocktails and enjoy the views on this two-hour tour.

Don't miss: Dance on the top deck to tunes played out by the onboard DJ. 

12.  Chicago Fireboat Tours Historical and Architectural Cruise

Hosted on the bright red Fred A. Busse Fireboat – which served the Chicago Fire Department until 1981 – this architectural tour of the Chicago River lasts anywhere from 90 minutes to two hours. A docent will fill you in on the history of buildings lining the river as well as the story of the boat you've boarded, which formerly traveled the city's waterways to fight fires. 

Don't miss: Check out the vintage firefighting artifacts and photos on board. 

Lady Grebe Chicago River Experience

13.  Lady Grebe Chicago River Experience

Want to feel extra posh? Grab a group of up to six friends and book a private cruise aboard Lady Grebe, a 48-foot vintage yacht that can be reserved for two-hour trips along the Chicago River. The reservation comes with a premium drinks package and you can also opt to kick things up a notch with picnic baskets full of food or full-service catering. 

Don't miss:  Book a Chicago Architecture Center docent to give a guided tour for an educational twist.

Chicago Electric Boat Company Tour

14.  Chicago Electric Boat Company Tour

Go your own way. Be your own captain. That’s what’s on offer with this Chicago River tour. The Chicago Electric Boat Company lets passengers steer the ship themselves (if they’ve got a valid driver’s license and watched a 10-minute tutorial, that is), allowing total freedom on the Windy City’s waterways. If you’re looking to still have some kind of tour, you can hire a personal tour guide—and we haven’t even gotten to the best bit. These boats are all electric, so they’re a little bit more environmentally friendly, too.

Don't miss: Hot tub boat rentals are also available.

Chicago Architecture Center River Cruise Aboard Chicago’s First Lady

15.  Chicago Architecture Center River Cruise Aboard Chicago’s First Lady

There's a reason the Chicago Architecture Foundation's beloved tour has been named the Best Boat Tour in the U.S.  The center’s official tour goes into detail on more than 50 buildings both on the riverfront and beyond. In doing so, they give a fascinating history of the city and those that built it—plus you can easily upgrade your ticket to include entry to just Chicago Architecture Center itself. It’s a proper design enthusiast’s dream. This one leaves from the Chicago First Lady Cruises dock and lasts around 90 minutes. 

Don't miss:  Gather friends for the serene evening cruise for just a few dollars more.

GYG Chicago TTD

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Unforgettable views. Unparalleled experiences.

Cruises & Tours

Explore chicago by land, water or air.

Whether you’re in town for just one day or are a life-long resident, cruises and tours of Chicago are a great way to see the sights, discover something new, or treat yourself to an unforgettable experience.

From laid-back sightseeing cruises and elegant dining cruises to heart-pumping thrill rides to upscale private charters, Lake Michigan and Chicago River cruises departing from Navy Pier offer a memorable experience for all.

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Our Cruises & Tours

cruises and tours 3

Architecture & Sightseeing Cruises

Take in Chicago’s iconic skyline and the scenic Chicago River with sightseeing cruises at Navy Pier! These fun experiences offer guests panoramic city views along with entertaining and enlightening commentary about Chicago’s architecture and history.

cruises and tours 4

Brunch, Lunch and Dinner Cruises

When you dine on Like Michigan, every table is the best in the house. Navy Pier’s brunch, lunch and dinner cruises pair world-class cuisine with panoramic views of the city and lakefront.

cruises and tours speedboat tours and extreme thrill rides 1

Speedboat Tours and Thrill Rides

This isn’t your parents’ leisure cruise! On these 30-minute speed boat rides, you’ll tear across Lake Michigan at up to 45 miles per hour while getting entertaining and informative commentary on Chicago.

cruises and tours specialty and holiday cruises 1

Specialty and Holiday Cruises

There’s always something worth celebrating with cruises on Lake Michigan and the Chicago River. Our partners offer themed cruises for major holidays, as well as a wide variety of special events that are sure to get you in the party mood.

odyssey lake michigan

Groups And Private Charters

Perfect for corporate outings and special occasions, group cruises and private charters offer unforgettable experiences for up to 800 guests.

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Bicycle Tours

Bike & Roll Chicago allows guests to rent bicycles for a fun experience on the lakefront.

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Our Cruise Partners

Discover our partners: Spirit Of Chicago, Shoreline Sightseeing, Seadog Cruises, Odyssey Lake Michigan, Mystic Blue, Chicago Elite Private Yacht, & Tall Ship Windy

Cruise & Tour Types

Shoreline Architecture River Tours

Shoreline Architecture River Tours

Take Shoreline’s award-winning 75-minute Architecture River Tour to discover Chicago’s renowned landmarks as presented by our expert and entertaining guides. You’ll learn how Chicago rose...

City Cruises – Premier Dinner Cruise on Lake Michigan

City Cruises – Premier Dinner Cruise on Lake Michigan

Lake Michigan dinner cruises are the perfect setting for celebrating with friends, connecting with colleagues, or a romantic evening. Odyssey Lake Michigan dinner cruises are...

City Cruises – Premier Lunch Cruise on Lake Michigan

City Cruises – Premier Lunch Cruise on Lake Michigan

A two-hour Lake Michigan lunch cruise is the perfect way to enjoy time with family or the company of great friends. Retreat from a busy...

City Cruises – Signature Dinner Cruise on Lake Michigan

City Cruises – Signature Dinner Cruise on Lake Michigan

Celebrate a special occasion, host a group event or share a romantic evening aboard Spirit of Chicago. Great for parties of all sizes, a Spirit...

City Cruises – Spirit of Chicago Dinner Cruise

City Cruises – Spirit of Chicago Dinner Cruise

Catch the Chicago skyline at sunset during the most beautiful time of the year, and join us for a fun, laid-back, 2-hour cruise. Spirit's Lakefront...

City Cruises – Odyssey Lake Michigan Dinner Cruises

City Cruises – Odyssey Lake Michigan Dinner Cruises

Odyssey Lake Michigan presents special prix fixe dinner cruises, offering guests the opportunity to try one of Chicago’s most unique dining experiences at an incredible...

City Cruises – Spirit of Chicago Brunch Cruises

City Cruises – Spirit of Chicago Brunch Cruises

Whether you’re a native Chicagoan, newcomer, or just visiting, a Spirit of Chicago brunch cruise is the perfect weekend outing. See well-known Chicago attractions from...

City Cruises – Signature Lunch Cruise on Lake Michigan

City Cruises – Signature Lunch Cruise on Lake Michigan

With the sunshine reflecting off the lakefront, there’s no better place to enjoy an afternoon in Chicago than aboard a lunch cruise. Departing from Navy...

City Cruises – Seadog River and Lake Architecture Tour

City Cruises – Seadog River and Lake Architecture Tour

Enjoy Chicago’s iconic skyline with an exciting architecture cruise on the Chicago River. Departing from Navy Pier, this 75-minute narrated cruise is the best way...

City Cruises – Seadog Lakefront Speedboat Tour

City Cruises – Seadog Lakefront Speedboat Tour

Our Lakefront Speedboat Tour is the best way to view Chicago from the lake, combining an exciting speedboat ride along the shoreline with informative and...

City Cruises – Seadog Extreme Thrill Rides

City Cruises – Seadog Extreme Thrill Rides

With exhilarating high speeds and full 360° spins, this jet-propelled ride blasts off to start and splashes down to stop. Experience full throttle slalom runs,...

City Cruises – Odyssey Lake Michigan Brunch Cruise

City Cruises – Odyssey Lake Michigan Brunch Cruise

This two-hour brunch cruise on Odyssey Lake Michigan, departing from Navy Pier, is ideal for capping off an incredible weekend. Enjoy a delicious menu stocked...

City Cruises – Odyssey Lake Michigan Groups

City Cruises – Odyssey Lake Michigan Groups

Host a truly unforgettable event on Lake Michigan. Book your group aboard one of Odyssey's regularly scheduled lunch or dinner cruises, or have an event...

Shoreline Sightseeing Group Tours

Shoreline Sightseeing Group Tours

Adventures are meant to be shared. Turn your next family gathering or corporate outing into an awesome adventure by booking with Shoreline. We offer special...

City Cruises – Chicago Elite Private Events

City Cruises – Chicago Elite Private Events

It's your yacht. Let our professional event planners create a custom event just for your group aboard the Chicago Elite. With two fully enClosed ,...

City Cruises – Seadog Groups

City Cruises – Seadog Groups

Planning a special outing for your group? Charter Seadog for an event everyone will enjoy! With the ability to travel both the lake and river,...

Shoreline Sightseeing Water Taxis

Shoreline Sightseeing Water Taxis

Shoreline Sightseeing’s water taxis are a great way to get around town. Starting in May and running through September, our water taxi service offers fast...

City Cruises – Spirit of Chicago Group Cruises

City Cruises – Spirit of Chicago Group Cruises

Host an event unlike any other in the city! Book your group aboard one of Spirit’s regularly scheduled lunch, brunch, cocktail or dinner cruises, or...

City Cruises – Premier Brunch Cruise on Lake Michigan

City Cruises – Premier Brunch Cruise on Lake Michigan

Experience the city’s most unique floating event venue! City Cruises offers all-inclusive packages, chef-prepared menus, full bar options, and entertainment customized to fit your needs—all...

City Cruises – Signature Brunch Cruise on Lake Michigan

City Cruises – Signature Brunch Cruise on Lake Michigan

Shoreline Skyline Lake Tours

Shoreline Skyline Lake Tours

Shoreline’s 40-minute Skyline Lake Tour offers a relaxing way to experience the panoramic of the city’s famed skyline as seen from majestic Lake Michigan. The...

Tall Ship Windy Chicago Skyline Sail

Tall Ship Windy Chicago Skyline Sail

Tall Ship Windy is closed for the season and will reopen in May 2024. Visit the Tall Ship Windy website to stay up to date...

Tall Ship Windy Private Charters & Weddings in Chicago

Tall Ship Windy Private Charters & Weddings in Chicago

A Beautiful Stage for Your Event Set sail on Windy for weddings, parties, corporate functions, reunions, church outings, tour groups, team building and more! Windy...

boat-tour

Your guide to Chicago lake and river cruises

One of the best ways to see Chicago is from the water. The city is home to two stunning waterfronts — the Chicago River and Lake Michigan — and each offers plenty of cruise options. Admire the skyline on a lakefront cruise, learn about the city’s iconic architecture on a Chicago River cruise, enjoy dinner and dancing aboard an all-glass vessel, sip cocktails on a tiki-themed boat, paddle your own kayak — the options are truly endless. Here’s your guide to Chicago lake and river cruises, boat tours, dinner cruises, and beyond.

See it all with Shoreline Sightseeing

Shoreline Sightseeing boat cruise on the Chicago River

One of Chicago’s classic cruise options, Shoreline Sightseeing covers all the bases. Their ultra-popular Architecture River Tour takes you on all three branches of the historic Chicago River takes you past dozens of landmark buildings.

They also offer skyline lake tours, plus specialty cruises and holiday events. Hop on a boat at Navy Pier or on Michigan Avenue.

Dine on the water with City Experiences

Odyssey River Cruise

City Experiences dining cruises are the perfect way to create a memorable moment in Chicago. Choose from a river or lake dining cruise, complete with delicious cuisine, cocktails, and entertainment.

Their glass-enclosed river vessel is particularly stunning. It offers passengers panoramic views of the city’s most iconic buildings as you glide along the Chicago River. They also offer lakefront brunch and dinner cruise options that depart from Navy Pier.

Entertain the family with Wendella Boats

sailboat tour chicago

For three generations, Wendella Tours and Cruises has been cruising the Chicago waterways. With its variety of tour options, cruise times and lengths, and a heated, enclosed cabin, Wendella is a great choice for families looking for flexibility. Choose from lake & river architecture, sunset cruises, and more.

Admire architecture with Chicago’s First Lady

An architecture boat cruise on the Chicago River

Around the world, Chicago is known for its outstanding architecture, and it’s easiest to admire the city’s legacy from the water. By partnering with the Chicago Architecture Center , Chicago’s First Lady offers the most comprehensive tour of the skyline — docents must train 100 hours before they can lead tours.

Speed across Lake Michigan on Seadog Boat Tours

Seadog Boat Tour

Are you up for a thrill? Race across Lake Michigan on SeaDog Cruises, featuring 30 minutes of high speeds and exhilarating twists and turns. Come prepared to get splashed.

SeaDog also offers lakefront speedboat tours and a river/lake architecture tour, featuring views of Chicago’s iconic Buckingham Fountain, Grant Park, Museum Campus, and more.

Live it up on an Island Party Boat

Looking for a party? These tiki-themed boats are always a good time, offering drink packages, stellar views, and fun vibes. You can hop on an Island Party Boat at Monroe Harbor or the Chicago Riverwalk, which is also where you’ll find their beach-inspired bar Island Party Hut. Choose from a river cruise, lake cruise, tacky tour guide cruise, or even a dueling pianos cruise.

Go back in time with Chicago Fireboat Tours

Step onto a real, historic fireboat and get ready for a unique experience with Chicago Fireboat Tours . The river tours are given aboard a real piece of Chicago history — a retired fireboat that patrolled the Chicago from 1937 to 1981. Tours are led by expert docents and include historic and sunset options.

Splurge on a Free Spirit Yacht Cruises

Looking to splurge a little? These private yacht charters are the way to go. The spacious yachts comfortably fit up to 49 or 120 people, making them the perfect option for a large celebration or an intimate gathering. Premium bar and catering packages round out the experience.

Explore the Chicago River with Urban Kayaks

Kayaking in Chicago

If you’re ready to ditch the captain and explore the water on your own, then it’s time to grab a paddle at Urban Kayaks . You’ll go through a brief training session before you hit the water, but you’re free to paddle the river or lake at your own pace. Or join in a guided tour to catch the sunset, fireworks, or historic highlights. Rentals are available at the Chicago Riverwalk or Monroe Harbor.

Rent an electric boat

Boat Bike from Chicago Electric Boat Company

Chicago Electric Boat Company offers fun and unique ways to get out on the water, including donut boats, retro boats, and even a bike boat that your group can pedal down the Chicago River. Rental locations include Marina City, the Chicago Riverwalk, and Rockwell on the River in Avondale.

See the skyline aboard Mercury Cruises

While Chicago’s summer fireworks are already fun to watch, it’s an entirely new experience when you’re on a 3D tour. Before the show, you’ll cruise around the lake and see some of Chicago’s famous landmarks.

Mercury Cruises also offer Urban Adventure, Canine Cruises, and Chicago by Night tours.

Check out Chinatown via Chicago Water Taxi

Chicago Water Taxi Boat Tour

Hop on! The Chicago Water Taxi is a fun and cheap way to get around Chicago. The Water Taxi stops at Ogilvie Transportation Center, Chinatown, Goose Island, the Chicago Riverwalk, Michigan Avenue, and River North. Get a one-way ticket for $6 or an all-day pass for $10. Check their daily routes and schedules for more details. Cruises.

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Shoreline Sightseeing Company

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Special Event Venues

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Urban Kayaks

Urban Kayaks

River North

Wendella Tours & Cruises

Wendella Tours & Cruises

The Magnificent Mile

Chicago’s First Lady Cruises

Chicago’s First Lady Cruises

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Chicago River Architecture Tour

Chicago's Original Architecture Tour®

Experience the city’s legendary architecture from the best seat in the house—the river. Our experienced tour guides detail the 130 year long history behind the skyline, while our bartenders and staff keep you comfortable and entertained. This comprehensive tour navigates through the heart of the city on all three branches of the Chicago River. It’s the one thing everyone tells you to do in Chicago, done right.

sailboat tour chicago

Schedule & Tickets

  • Adult: $44.00
  • Child (4-12): $20.00
  • Under 4: Free (ticket required)

TICKETS ARE NON REFUNDABLE BUT ARE TRANSFERABLE.

  • Parking & Directions
  • More Information
  • COVID-19 Safety
  • Boarding begins 15-30 minutes prior to scheduled departure time.
  • All bags are subject to inspection.
  • Prohibited Items: Outside Alcohol, Weapons of any kind (Firearms, Knives, etc.), Flammables, Explosives.

Your boat includes:

Drinks & Snacks

Full-service bar with wine, local beer, and craft cocktails, as well as an assortment of snacks, all for purchase. Pinkies up!

Expert Tour Guide

Never boring, always entertaining.

Accessibility

Everyone should be able to enjoy our tours. We make sure you can.

No need to hold it. We have changing tables for the little ones who don’t know what holding it is.

Climate-Controlled Lounge

Keeping you cool when it's warm and warm when it's cool (or freezing).

*Not all amenities are available on every vessel.

BOOK YOUR EXPERIENCE NOW

sailboat tour chicago

sailboat tour chicago

Chicago River Boat Architecture Tours

Chicago River Tours | Fireworks Tours | Jazz/Cocktail Tours

River Boat Tours

Book your tour now, book by phone: (708) 488-6343, about the tours, chicago river boat architecture tours .

Welcome to Chicago River Boat Architecture Tours!  We’re proud to present you with an in-depth, expert architectural-based river boat tour that delves into one of the most remarkable American cities today. Known for unique, daring, and historical architectural pursuits, it’s hard to cover all of the design and building treasures that make up the Windy City today. If you’re ready to learning more about the designs, people, and innovations behind these creations, throw on your captains hat and get ready to cruise along the Chicago River and see what architects from around the world travel to see in Chicago.

About The Chicago River Boat Architecture Tours

Chicago is known around the world for its architectural feats, both inside and outside of the buildings. From the 100-year-old Art Deco, Neo-Classical, and Gothic Towers, to some of the tallest modern-day skyscrapers, Chicago is where old meets futuristic architectural endeavors. It has something for everyone in a way that no other city replicates today.

Why Tour Chicago’s Architecture with Us?

We are born-and-raised Chicagoans ourselves, passionate about the community that we know and love. That passion and desire spills into all of our tours, drawing on personal experiences for curating a tour that just can’t be duplicated by a book or a movie. We want you to experience everything firsthand. Why tour with us?

  • Expertise: All of our tour guides are either architects, architecture students, or architecture historians, making for an in-depth and personally rooted kind of touring experience that covers all of the discreet details.
  • Variety: We offer a variety of uniquely different tours that cover everyone’s individual taste. We offer the Chicago River Boat Architecture Tour that takes you down the famous Chicago River; there are several different options such as Architecture, History, Cocktail Cruises and Firework Viewing Tours
  • Flexibility : We want you to enjoy your Chicago River Boat touring experience, which is why we’re happy to talk with you and learn more about how our tours can accommodate you, your party, or your corporate outing. Our tours run daily, with availability always posted on our website here.

Our Tours  

  • Chicago River Boat Architecture Tour : When in Chicago, cruising down the Chicago River is  a must. Except with us, you’ll be taking in the architecture of the buildings that line the beautiful river. We provide detailed explanations of the construction and history of over 50 significant buildings, wrapping up at the end of the river.
  • Chicago River Boat Cocktail Tour : Join us for this great Architecture Tour while sipping craft cocktails, beer or wine available for purchase at our bar on board!
  • Lake Michigan Navy Pier Fireworks Cruise :  Fireworks, one of the Four Great Inventions of ancient China were invented in the 12th century. Chicago approved City-Wide Use of Fireworks on the 4th of July 1893,. Mayor of Chicago Patrick Eugene Prendergast issued a proclamation approving the use of fireworks to celebrate the World’s Colombian Exposition and to celebrate the nation’s 117th Independence Day. This fascination with fireworks, noise, and color continues today. The City of Chicago offers a fireworks show at Navy Pier on Saturday nights at 10:15 p.m. The Fireworks Cruise sails on both the Chicago River and Lake Michigan each Saturday at 8:30 pm.

Our Commitment to Your Touring Experience

We believe that tours should be entertaining, enlightening, informational, and perfectly organized, every single time. A tour shouldn’t feel laborious in any way; you should feel an effortless inclination to learn more about what we present at your fingertips. With our Chicago architectural tours, that’s exactly what we strive to provide, basing each tour from the perspective of an expert with the real-life example in the background.

If you’re thinking about booking a tour with us, know that our commitment to flexibility and accessible makes our Chicago Architecture Tours easy and convenient:

  • 3 pm *Not Available Friday thru Sunday Summer Months*
  • 6:30 pm (Jazz Band, Cocktail w/bar) *Sunday Only*
  • 8 pm (Wednesdays)
  • 8:30 pm (Saturdays)
  • Seniors $48
  • Youths $30 (7-12 years old)
  • Children 6 and under Free

BOOK YOUR TOUR TODAY

Click Here to Purchase a Gift Certificate

Chicago river boat cocktail tour.

sailboat tour chicago

Join us in the evening to sip cocktails while cruising the historic Chicago River! Get the same tour just with a cocktail in your hand! Premium bar on board with craft cocktails, wine and beer available for purchase. Drinks may be purchased individually with a credit card on the boat. Tour Information Pricing Adults $49… Continue reading Chicago River Boat Cocktail Tour

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Chicago river boat architectural tour.

sailboat tour chicago

Forming a length of 156 miles when combined, the Chicago River is a system of rivers and canals the characterize the infamous skyline of Chicago today. The river, running through the city, including the city center Chicago Loop, is evident of man made design and infrastructure when completed craftily. In 1887, the river was reversed… Continue reading Chicago River Boat Architectural Tour

Lake Michigan Navy Pier Fireworks Cruises (w/ Architecture Tour)

sailboat tour chicago

Enjoy your favorite drink while gazing Chicago’s magnificent architecture and finish your cruise with fabulous light show, at Navy Pier. Fireworks, one of the Four Great Inventions of ancient China were invented in the 12th century. Chicago approved City-Wide Use of Fireworks on the 4th of July 1893,. Mayor of Chicago Patrick Eugene Prendergast issued… Continue reading Lake Michigan Navy Pier Fireworks Cruises (w/ Architecture Tour)

  • GET DIRECTIONS
  • Cruise Information
  • Architectural
  • St. Patrick’s Day
  • Private Events

COVID-19 SAILING PROTOCOL >

sailboat tour chicago

The safety of our Passengers and Crew has always been our number one priority of Chicago Line Cruises.

Therefore, in light of the increased number of Covid cases in Chicago and throughout Illinois, we will be ending our 2020 Sailing Season effective immediately.

We sincerely thank all of our customers and business partners who have supported us during these challenging times.

We’re excited for the 2021 Season and hope to see you onboard very soon!

Terry Johnson

Owner – Chicago Line Cruises

OUR 2024 SEASON OPENS ON ST. PATRICK’S DAY WEEKEND!

Check back for our sailing schedule, check our sailing schedule.

sailboat tour chicago

St. Patrick's Day River Cruise

Duration : 90 MINUTES

ST. PATRICK'S DAY RIVER CRUISE

SATURDAY, MARCH 16, 2024 Kick off the season and celebrate St. Patrick’s day with us! Come experience the luck o' the Irish on the infamous green Chicago River aboard our flagship Ft. Dearborn.

Tickets: $110     Times: 10:00 am, 12:00 pm, 2:00 pm, 4:00 pm

Eco Cruise Chicago

TUESDAY OCTOBER 8, 2019 We are excited to announce that we will be partnering with 2019 Chicago Architecture Biennial, The School of the Art Institute of Chicago and NEXT.cc to present Eco Cruise Chicago!

Adults : $44    Seniors : $41    Youths : $22    Children 6 and under : Free

sailboat tour chicago

Architectural Cruise

Architectural cruise.

Think of the Venetian canals, a Shinto temple, the medieval Cathedral in Chartres, or the unmistakable skyline of Chicago. Each year thousands of architecture lovers travel to the City of Chicago, the birthplace of the skyscraper… and thousands book passage aboard our enthralling river tour, widely considered the best 90-minutes spent in Chicago.

Adults : $50    Seniors : $48    Youths : $30    Children 6 and under : Free

sailboat tour chicago

The Mild West Concert Cruise

The mild west concert cruise.

SATURDAY, AUGUST 19, 2023 Set sail with pop/rock outfit The Mild West for a night of rock n’ roll down the Chicago River! Chicago Line Cruises is turning their 65-foot, two-deck Ft. Dearborn into an outdoor music venue that cruises the Chicago River to highlight local talent and bring you all the live music you missed last summer!

Adults : $40    Seniors : $40    Youths : $40    Children 6 and under : Free

sailboat tour chicago

Cocktail Cruise

Cocktail cruises.

Sip your favorite cocktail as the towering sunlit majesty of Chicago's skyscrapers gives way to the breathtaking, burnished hues of early evening. Many people say it's the most beautiful time of day for a cruise. Your Docent will describe Chicago’s famous towering structures in a fully narrated architectural cruise as they are majestically lit by the hues of early evening.

Adults : $48    Seniors : $46    Youths : $28    Children 6 and under : Free

sailboat tour chicago

Architectural Cruise with Fireworks

Duration : 2 HOURS

ARCHITECTURAL CRUISE WITH FIREWORKS

In 1893, Mayor of Chicago, Patrick Eugene Prendergast, issued a proclamation approving the use of fireworks to celebrate the World's Columbian Exposition and to celebrate the nation's 117th Independence Day. Enjoy your favorite drink while gazing Chicago’s magnificent architecture and finish your cruise with a fabulous light show at Navy Pier!

Adults : $48    Seniors : $46    Youths : $26    Children 6 and under : Free

sailboat tour chicago

Historical Cruise

Historical cruise.

Sail with us and learn how the Great Chicago Fire of 1871 jumped a river and cleared the way for visionaries of plate glass and structural steel such as Jenney, Root, Burnham and Sullivan (Wright's mentor). In less than a decade, the Chicago School of ingenious grillage foundations and steel-frame construction techniques lifted all architecture heavenward.

sailboat tour chicago

Live Jazz Cruise

Live jazz cruise.

Be immersed in iconic Chicago Jazz while cruising the historic Chicago River! Live Music by internationally known jazz guitarist, Geordie Kelly & his band. The Chicago style of Jazz came out of both the Mississippi Delta and New Orleans “Dixieland” with pioneer musicians like Louis Armstrong & King Oliver creating its unique sound.

Adults : $50    Seniors : $50    Youths : $50    Children 6 and under : Free

OVERVIEW OF CHICAGO LINE’S

sailboat tour chicago

MERCHANDISE

Never forget your onboard experience on your Chicago Line cruise. Be sure to purchase one of our stylish souvenirs today!

sailboat tour chicago

COMPLIMENTARY

Starbucks Coffee, Twinings Tea, Coca-Cola soft drinks and lemonade are all complimentary.

sailboat tour chicago

BEER, WINE & COCKTAILS

Beer, wine and cocktails are available for purchase at any time.

CHICAGO LINE CRUISES

Sail with us, make your moments memorable with chicago line cruises.

sailboat tour chicago

PRIVATE EVENTS

For parties up to 170, we have fully-outfitted boats and onboard amenities to help you create a private event they’ll talk about for years to come.

DO YOU HAVE A GROUP OF 20 OR MORE? CONTACT US FOR SPECIAL RATES!

sailboat tour chicago

Group discount rates are available for parties of 20 or more aboard any of our river cruises.

GIVE THE GIFT OF CHICAGO LINE TOURS!

sailboat tour chicago

GIFT TICKETS

To give a special someone, friend or client the best tour in Chicago, simply ask at our ticket office or contact us.

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Chicagolinecruises.

Celebrating Chicago by boat since 1981 with Architectural, Firework and Private Cruises!

Chicago Line Cruises

This is my 8th time on a Chicago architectural river cruise and this was by far the most informative and biggest bang for your buck. Operagolf / LaHabra
The best guide on our whole USA trip. We took the Architecture tour where the boat meandered in between all of the incredible buildings of the city with the guide knowing EVERYTHING about each building; its style, age, height, architect, cost, purpose, owner ….. Quite brilliant! DrCumbrian / TripAdvisor
I've done several of the architecture cruises since my family moved to Chicago, and this is the best one yet! Allie K / TripAdvisor
If you only have time for one sight-seeing event while in Chicago, do this. We really have no great interest in architecture, but this tour came highly recommended and we did not regret it. Allice I / Oklahoma
My wife and I very much enjoyed the Chicago Line Cruise jazz cruise... My spouse said this was one of the favorite things she has done in Chicago since moving here in the past year, and I agree. I am a jazz snob, and ... I was very pleased with the music offered by the Geordie Kelly group. He's a fine jazz guitarist, and his band was great. Augie R / Yelp

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Architecture Tour

TripAdvisor users rank the Chicago Architecture Center River Cruise aboard Chicago's First Lady as the city's #1 boat tour.

There’s one sure recipe to make your business or social event even more memorable – just add water and Chicago’s First Lady!

Recalling the handsome elegance of 20th century luxury yachts, our vessels are sure to make an impression. Choose from seven perfectly sized ships for your private event.

Your wedding is the start of your lifelong journey together, so begin that journey in a truly memorable way - a wedding cruise down the Chicago River.

Evening River Cruise

Experience our renowned daytime CAC River Cruise in the glow of the setting sun. Take in the city’s magnificent architecture bathed in golden light as it begins its transition from day to night.

sailboat tour chicago

“The very best city tour I have been on in my life! We were in America for a month and this was our best morning.” - JurassicBill TripAdvisor, Dorset UK

- Latest Articles -

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Top Occasions to Celebrate on the Chicago River

The Chicago River, with its winding beauty amidst the city’s architectural wonders, offers a unique backdrop…

sailboat tour chicago

Appreciating What Chicago's Unique Waterways Have to Offer

If you've always dreamed of creating a truly unforgettable wedding experience, consider sailing into…

sailboat tour chicago

Cruise into Happily Ever After Aboard Chicago's First Lady

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"What an amazing experience, this tour brings all the beautiful architecture and history to life.” - Rachel M Yelp, Arizona, USA

sailboat tour chicago

7 things that might surprise you about the Chicago Architecture Boat Tour

T here are plenty of ways to take in the sights, sounds (and smells) of Chicago, but you don't necessarily have to be on land to do that.

And you don't have to be a tourist, either.

In fact, one of the most beloved ways — among locals and visitors alike — to experience city is by journeying across the Chicago River and Lake Michigan while a tour guide talks about buildings and regales you on the untold story of Mrs. O'Leary's cow.

In other words: a Chicago Architecture Boat Tour.

"As you're going up and down the Chicago River and on Lake Michigan, you're seeing the city’s evolving architecture, which is changing every year" said Andrew Sargis, director of sales and marketing for Wendella Tours and Cruises .

Wendella, billed as Chicago's "original" architecture tour, in 1935 gave its first architecture tour of the city from a wooden diesel yacht out on Navy Pier, Sargis said. Now, upwards of 20 architecture tours are offered daily, with more on the weekends. On average, Wendella tours see roughly 100,000 passengers each month over the summer, Sargis said.

And though the majority of guests on any given Wendella architecture tour are tourists, Sargis said, locals take them, too.

MORE: Even Chicagoans can't get enough of this tourist attraction: ‘It's about the only touristy thing I do'

"I was surprised when I first started, we get a lot of repeat locals," Bobby Scheffle, a Wendella tour guide told NBC Chicago. "And always there's a lot of local people that come on when they have guests visiting them in town. They like to show off the city this way."

But there's something else about the experience that makes it so very Chicago.

"I think it is really unique to experience the city from a boat on a river, because we think about other big cities in the United States -- there aren't many that have a river that go right through downtown," Scheffle said. "You feel like you're in the city, you hear the noise, and you see the buildings and all that."

Whether you're taking the ride for the first time or the 50th, bringing out-of-town guests out for a memorable activity or just itching to be a tourist in your own city, here are seven things to know about the Chicago Architecture Boat Tour.

Will weather stop a tour from running?

Wendella's architecture tours run year-round, Sargis said, although "weather is a factor."

Weather events like ice on the river or significant snowfall can impact operations, Sargis said, but they typically don't, since the Chicago River -- a federal waterway -- must remain navigable year-round.

While Wendella's boats do have climate-controlled indoor lounges, tours during the winter may run at limited times. But rain, snow, extreme heat or wind, unflappable Chicagoans still show up.

"We went on drizzly day a few years ago," Kathy Rambo wrote on NBC Chicago's Facebook page. "There were only about 10 of us on the boat!

And most often, the tour will run — rain or shine — so don't hesitate to bring a raincoat.

"I have certainly [given tours] under thunderstorms and downpours, and I've gotten drenched sometimes," Scheffle said. "I've never had a tour get canceled because no one bought a ticket. There's always someone wanting to come out here in the rain or the cold."

What's the best time of year (or day) to go?

It depends on when exactly your favorite time of the year is, and what you're hoping to see.

For Sargis, it's late summer. "There's this point of time in September when the weather is beautiful, but there's not that summer rush."

There are other times that Chicagoans may want to consider, too.

"St. Patrick's Day Celebration when they dye the river, and any Wednesday or Saturday night [over the summer], watching the fireworks over Lake Michigan , especially if you're local" Sargis said.

During the summer months, Wendella's tours run start as early as 9 a.m., with the day's final tour not ending until 10 p.m. or 11 p.m., Scheffle said, "so if you want to come for a ride to see the city lights, you can come late, and it's also beautiful, just a little more difficult to see the colors on the buildings if that's what you want to see."

Laura Pubins, who lives in a suburb outside of Chicago, agrees.

"My favorite one was when we were on a boat at sunset," Pubins wrote to NBC Chicago on Facebook. "It was an awesome new view of the city."

What's the most photogenic spot on the tour?

For Sargis, it's "anything out on Lake Michigan," with the skyline in the background.

On the river though, there's one moment that captures the city best, Scheffle said, no matter what time of day you're taking the trip.

"The best place to take a photo on the 90-minute river tour is when we come up the south branch from Chinatown," Scheffle said. "That's the best place because you get the whole skyline from the south. It's really beautiful."

For locals though, it may not be what you're looking at, so much as how you're looking at it.

"You're looking at [the city] from underneath," said Chicago resident Nick Pappas, 55, who recently found himself on a 90-minute river tour. "It's just a different perspective on the river that you don't get on the street level. As amazing as that sounds, you're only, like, 20 feet down, but it gives you a whole different perspective."

What does the training for a tour guide look like?

According to Sargis, all Wendella tour guides are trained in-house -- and the spots are competitive.

"There's high demand," Sargis said, of the position. "There are more people that want to be tour guides than space available. It's certainly a popular job, and people want to do it." While the tour guide of any given architecture tour isn't made public, many people do request certain ones for private events, Sargis said.

For the tours, there's a general script, with highlights that must be mentioned, Sargis said. But improvisation, along with sharing personal history is encouraged, too.

"All of the tour guides have their own experience in the city, and will add parts of their history in it," Sargis said. "We have a tour guide that is a retired police officer, and he will interject anecdotes form his career. We have a tour guide that's a Vietnam War Veteran, and when we go by the Vietnam War Memorial, he will always discuss the importance of it to him."

For Scheffle, the training included joining multiple tours a week for two weeks and flashcards.

"For a while, I, just drove Uber and Lyft," Scheffle said. "And then, I remembered that I really liked Chicago. I like learning fun facts about it. And there are people in the city that have that as a job -- to tell people fun facts about Chicago and I started looking into tourism jobs in the city."

What's the most common question tour guides get?

Believe it or not, it's not always about The Great Chicago Fire , or Mrs. O'Leary and her cow, at least on Scheffle's tours.

"My favorite thing on the tour that happens is probably when little kids ask questions," Scheffle said. "The common question that a kid will ask, because I talk about the tallest building, second tallest building, third tallest building, a lot of times a kid will ask what's the shortest building in Chicago? Which I don't have a good answer for."

Are you supposed to tip your guide?

"It's up to the discretion of the client," Sargis said. "I would say a lot of our passengers do tip our tour guides."

What's the absolute best part of the tour?

Sure the tour is photogenic, and the city's history is fascinating. And though some may go on the tour to find out what buildings are new, others prefer to think about the old.

"My favorite building to talk about is probably the Board of Trade building," Scheffle said. "Just because I remember walking by it much younger and always, I remember, really being impressed by it, thinking was such a cool big city building."

For a local on the tour, the memories are nice. But a day out on the water in Chicago is just hard to beat.

"It's great. I don't have to work," said Pappas, who has lived in the city for 55 years. "Every time, it's a little treat to go down the river."

Video editors Ivonne Ramirez and DS Shin produced and created the video for this story.

The Reid Murdoch Building and Chicago River in Chicago, Illinois, United States, on October 16, 2022. (Photo by Beata Zawrzel/NurPhoto via Getty Images)

Chicago Boat Show, a McCormick Place staple, will move to Rosemont

Organizers said the relocation decision came after multiple conversations with exhibitors and market research..

A man walks by some of the vessels on display from dealer The Boat House at January's Chicago Boat Show at McCormick Place.

A man walks by some of the vessels on display from dealer The Boat House at January’s Chicago Boat Show at McCormick Place.

Tyler Pasciak LaRiviere/Sun-Times

The annual Chicago Boat Show will be moving next year out of its longtime home at McCormick Place, organizers announced Thursday.

After 92 years, Chicago’s largest boat show will debut at Rosemont’s Donald E. Stephens Convention Center on Jan. 8-12, 2025.

The decision came after multiple conversations with exhibitors, said Darren Envall, vice president at National Marine Manufacturers Association, organizer of the event. Market analysis and boater feedback were also factors for the shift to Rosemont, which is closer to suburban boaters.

“The more centralized Rosemont ... location positions the show for growth, accommodating the expanding boating population across a broader Chicagoland region,” Envall said in a news release.

Next year’s show is expected to feature more fishing boats, which cater to suburban and recreational boaters, a large customer base. The average boater’s income is $100,000 or less, Envall told the Sun-Times, so the convention will display more entry-level boats. However, the event will still showcase million-dollar yachts, he added.

Outdoor industries, including boating, became more popular during the pandemic when people could enjoy being outside while remaining socially distant from others, Envall said.

In 2022, the number of outdoor recreation participants grew 2.3% to a record high of more than 168 million people, or 55% of the U.S. population ages 6 and older, according to a 2023 report from the Outdoor Industry Association.

January’s Chicago Boat Show was expected to attract about 40,000 visitors from Illinois, Michigan, Indiana and southern Wisconsin. Exhibitors displayed some 400 fishing boats, deck boats, ski boats, wake boats, pontoons and yachts ranging in price from less than $10,000 to more than $1 million. But only 18,169 visitors turned out, said Envall, citing bad weather.

He expects next year's show to have 40,000 attendees, along with exhibitors from multiple states in the region.

In the last decade, the show has evolved from boats, recreational vehicles and sailing vessels to strictly a boat exhibition, which Envall said was also a deciding factor for moving to Rosemont.

Other outdoor industry events staging shows at the DES Convention Center include the Chicago RV & Camping Show, the Chicago Golf Show and the Travel & Adventure Show.

The DES Convention Center has 840,000 square feet of exhibition space, compared to 2.6 million square feet of exhibit halls at McCormick Place.

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Everything we know about D23: The Ultimate Disney Fan Event

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We now know all the details for D23: The Ultimate Disney Fan Event!

On Tuesday, Disney shared a sneak peek at what you can expect. This year, the event will feature three days of marquee showcases and presentations, an expanded show floor with the latest from Disney brands and partners, increased shopping opportunities, and a week-long celebration of Disney fandom leading up to the event.

Here's everything you need to know.

When is D23 in 2024?

Fans from around the world will once again gather in Anaheim, Calif. on Aug. 9, 10 and 11 for a one-of-a-kind experience showcasing the very best in creative storytelling and innovation from across The Walt Disney Company.

For the first time ever, the Honda Center will be home to three nights of marquee showcases.

  • Friday: The Disney Entertainment Showcase will feature exclusive looks at the movies, series, and stage shows fans love and a glimpse of what's next.
  • Saturday: Disney Experiences will feature the latest on new and highly anticipated projects in development around the world for Disney parks, experiences, and beyond.
  • Sunday: A special ceremony to celebrate the 2024 class of Disney Legends, hosted by Ryan Seacrest.

Disney Legends lineup

The Disney Legends Award honors artists and visionaries throughout the company's history who have pushed the envelope of creativity, challenged conventional wisdom, and broken the restraints of the status quo in search of new possibilities and excellence.

This year, the Walt Disney Archives is honoring Colleen Atwood, Angela Bassett, Martha Blanding, James L. Brooks, James Cameron, Jamie Lee Curtis, Miley Cyrus, Steve Ditko, Harrison Ford, Mark Henn, Frank Oz, Kelly Ripa, Joe Rohde, and John Williams.

The ceremony will take place at 5 p.m.

Go here to learn all about this year's 14 Disney Legends.

D23 Day at the Disneyland Resort

Before everything gets underway, guests can kick off the weekend's festivities at the first-ever D23 Day at the Disneyland Resort on Thursday, Aug. 8. Fans are welcome from rope drop to late night, featuring unique offerings for fans including a custom cavalcade, an energetic dance party, special photo opportunities, specialty foods, themed merchandise, and more at both parks. Disney Junior will also join the festivities and host a music-filled celebration at Disney California Adventure Park. Learn more here .,

sailboat tour chicago

The Anaheim Convention Center will once again showcase the best of Disney storytelling and innovation with an immersive and expanded show floor full of great experiences and activities for all ages. Fan-favorites will return including pavilions from Pixar, Walt Disney Animation Studios, Disney+, Marvel Studios, Disney Experiences, Lucasfilm, and a first-of-its-kind exhibition from the Walt Disney Archives entitled "A Great Big Beautiful Car Show."

Fans can take advantage of great shopping opportunities including a dedicated space to shop and experience limited-edition merchandise and collectibles. Other fan-favorite shopping destinations will return including Mickey's of Glendale, The Hollywood Studio Store, and The Emporium. Plus, The Walt Disney Company Store will make its debut and feature exclusive D23: The Ultimate Disney Fan Event branded products.

Guests will also have the opportunity to attend specially curated shows, panels, and presentations, along with conversations with storytellers, creators, and talent. These presentations will feature distinctly Disney content that will entertain fans of all generations on five different stages at the Anaheim Convention Center.

D23 Day at Angel Stadium

The first ever D23 Day at Angel Stadium will take place on Sunday, August 4, as the stadium comes to life with D23 fun. The first 23,000 fans through the gate will receive a commemorative and one-of-a-kind D23 Mickey Mouse bobblehead.

The Ultimate Disney Sweepstakes: Fantastic Prizes

Fans can also enter an unparalleled sweepstakes, one of the most expansive in Disney history. D23: The Ultimate Disney Sweepstakes - FANtastic Prizes is a spectacular lineup of exclusive prizes and engaging experiences that only Disney can deliver! One of the spectacular prizes includes a sailing on the seven-night maiden voyage of the newest Disney Cruise Line ship, the Disney Treasure.

How much do D23 tickets cost this year?

Tickets for all D23 Gold and General Members will go on sale starting March 26 at 12 p.m. PT.

  • D23 Ultimate Fan Pass 3-Day Ticket includes a 3-day assigned seat for evening shows at the Honda Center and 3-day access to all experiences at the Anaheim Convention Center-starting at $297/ticket.
  • D23 Ultimate Fan Pass 1-Day Ticket includes a reserved seat for that date's evening show at the Honda Center and same-day access to all experiences at the Anaheim Convention Center-starting at $99/ticket.
  • D23 Preferred Ultimate Fan Pass 3-Day Ticket, exclusive to D23 Gold Members, includes a 3-day floor seat for evening shows at the Honda Center (same seat each night), and 3-day access to all experiences at the Anaheim Convention Center-starting at $999/ticket.

The D23 Fan Pass provides access to the Anaheim Convention Center only:

  • 1-Day Pass: Gold Members: $79/ticket/General Members: $89/ticket
  • 3-Day Pass: Gold Members: $209/ticket/General Members: $259/ticket

D23 Gold Members will have first access to a number of 1-day and 3-day tickets for a limited time beginning March 26, 2024, at 12 p.m. PT.

D23 Gold and General Members who are also Visa cardholders, and who pay with their Visa card, will have pre-sale access to a number of 1-day and 3-day tickets, for a limited time and while supplies last, beginning March 27, 2024, at 12 p.m. PT.

Attendees must be a D23 Member to purchase tickets.

Fans can join as a complimentary General Member or upgrade to Gold Membership at JoinD23.com .

Disney is the parent company of this station.

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IMAGES

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  2. 14 Best Boat Tours in Chicago

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  3. 12 Best Boat Tours in Chicago

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  5. Chicago Boat Tours: Find the Best Lake and River Cruises

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  6. Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

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  2. Cruisers and Sailboat ~ August 19, 2023 ~ San Francisco Bay

COMMENTS

  1. Skyline Tour Aboard 148 Ft. Schooner Windy

    Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water. Windy is the Official Ship for the City of Chicago. At 148 feet long, she is one of only a few 4 masted Schooners built in the United States. You will enjoy a relaxing sail around aboard a ...

  2. THE TOP 10 Chicago Boat Cruises, Sailing & Water Tours (w/Prices)

    Climb aboard your 2,000-horsepower speed boat at Navy Pier, then hang on for the ride of a lifetime, as you zip past famous attractions like the Willis Tower, Grant Park, and Buckingham Fountain, pausing to learn a little about the history and architecture of the Windy City along the way. 30 minutes. from. $41.59.

  3. Tall Ship Windy Chicago

    Come enjoy the Chicago skyline as you sail on our tall ship! For groups or charters, email us at [email protected] or call us at: (312) 451-2700. The Tall Ship Windy offers the most spectacular fireworks experience during the Chicago summer. Our sails are both fun and educational, which makes them the perfect way to see Lake Michigan.

  4. THE TOP 10 Chicago Sailing Tours (w/Prices)

    Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago. 21. Soak up the views of Lake Michigan and the Chicago skyline with a 2-hour sailing tour. This private charter is completely customizable, giving you the chance to choose your music, route, and up to 5 additional guests.

  5. Chicago Skyline Sail

    Explore Chicago's scenic shores with a relaxing sail around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views and discover the Windy City from the water. Select from Pirates and Maritime Stories at 1pm, Architectural and Skyline Tours at 3pm and 5pm and Sunset…

  6. Windy City Sailing

    The yachts are at the North End of Belmont Harbor, just east of Wrigley Field—or 15 minutes from the Chicago Downtown area. Windy City Sailing is easily accessible via Uber, Lyft, taxis, and bicycles. Also, parking is available via the City of Chicago. Gift certificates are available for all Chicago sailboat cruises and bareboat charters.

  7. Come Sailing, Inc.

    Come Sailing is Chicago's premier sailing experience and private sailing charter offering a variety of boat rides, sailing charters, sightseeing tours, swimming trips, and customized private charters on Lake Michigan. Our focus is on charters for small groups of up to 6 passengers.Whether you're an experienced sailor or a person looking to try something new with the family, you're going to ...

  8. All Sails

    Chicago Skyline Sail Aboard 148' Tall Ship Windy. Explore Chicago's scenic shores with a relaxing sail around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views and discover the Windy City from the water. Select from Pirates and Maritime Stories at 1pm, Architectural and Skyline Tours at 3pm and 5pm and Sunset and ...

  9. Nebula

    The Nebula accommodates up to ten (10) guests and is ideal for relaxing on the Chicago Lakefront. The custom-made cushions provide comfort and relaxation during a leisurely cruise. Also, the large bimini (sunshade) provides protection from the sun on those hot summer days. Your party can easily jump into the lake and climb back aboard using the ...

  10. Chicago Sailboat Charters

    Chicago's top sailboat & yacht rental in Chicago & Lake Michigan. Chicago Sailboat Charters features multiple sailboats, multiple yachts, and one large 36 passenger big boat. Rent your Chicago boat by calling 773-236-7245

  11. The 15 best boat tours in Chicago

    Photograph: Barry Butler. 15. Chicago Architecture Foundation Center River Cruise. There's a reason the Chicago Architecture Foundation's beloved tour has been named the Best Boat Tour in the U.S ...

  12. Cruises & Tours in Chicago

    A Beautiful Stage for Your Event Set sail on Windy for weddings, parties, corporate functions, reunions, church outings, tour groups, team building and more! Windy... Explore Chicago's unforgettable views with cruises & tours by land, water, or air. Experience architecture, dining, and thrill rides from Navy Pier.

  13. Chicago Boat Tours: Find the Best Lake and River Cruises

    The Chicago Water Taxi is a fun and cheap way to get around Chicago. The Water Taxi stops at Ogilvie Transportation Center, Chinatown, Goose Island, the Chicago Riverwalk, Michigan Avenue, and River North. Get a one-way ticket for $6 or an all-day pass for $10. Check their daily routes and schedules for more details. Cruises.

  14. Chicago River Architecture Tour

    90 minutes. Buy Tickets. Chicago's Original Architecture Tour®. Experience the city's legendary architecture from the best seat in the house—the river. Our experienced tour guides detail the 130 year long history behind the skyline, while our bartenders and staff keep you comfortable and entertained. This comprehensive tour navigates ...

  15. Educational Tour and Sail Aboard Chicago's Official Flagship ...

    Chicago Architecture Center River Cruise aboard Chicago's First Lady. 1,734. 1 hour 30 minutes. Free Cancellation. From. $54.00. Small-Group Sightseeing Boat Tour in Chicago. 40. 2 hours.

  16. Top 10 Best Sailing Tour in Chicago, IL

    Reviews on Sailing Tour in Chicago, IL - Chicago Sailboat Charters, Tall Ship Windy, KnockOut Charters, Phenix Sailing Charters, Come Sailing, Chicago's First Lady, The Salty Dog Sailing Co., Chicago Architecture Center, Offshore Adventures, Shoreline Sightseeing

  17. THE 10 BEST Chicago Boat Rides & Cruises

    2.0 of 5 bubbles. & up. Navy Pier. City Experiences By Hornblower. Chicago River. Adler Planetarium. Set sail on your destination's top-rated boat tours and cruises. Whether it's an entertaining and informative boat tour or a relaxing sunset dinner cruise, these are the best Chicago cruises around. Looking for something more adventurous?

  18. Chicago River Boat Tours & Rides

    Chicago's First Lady offers various riverboat tours & rides with beautiful sightseeing of Chicago city. To explore our tours, contact us & book your tickets today! CRUISING SEASON 2024. March 17 - November 24. Location ... TripAdvisor users rank the Chicago Architecture Center River Cruise aboard Chicago's First Lady as the city's #1 boat tour. ...

  19. Chicago River Boat Architecture Tour: Guided Chicago River Boat Tours

    BOOK YOUR TOUR NOW . Book By Phone: (708) 488-6343 About The Tours . Chicago River Boat Architecture Tours Welcome to Chicago River Boat Architecture Tours!We're proud to present you with an in-depth, expert architectural-based river boat tour that delves into one of the most remarkable American cities today.

  20. Chicago Boat Tours

    Each year thousands of architecture lovers travel to the City of Chicago, the birthplace of the skyscraper… and thousands book passage aboard our enthralling river tour, widely considered the best 90-minutes spent in Chicago. Adults: $50 Seniors: $48 Youths: $30 Children 6 and under: Free. Learn More Purchase Tickets.

  21. Best Chicago River & Lake Cruise

    TripAdvisor users rank the Chicago Architecture Center River Cruise aboard Chicago's First Lady as the city's #1 boat tour. Chicago Architecture Center River Cruise aboard Chicago's First Lady Learn More. Private Events. There's one sure recipe to make your business or social event even more memorable - just add water and Chicago's ...

  22. 7 things that might surprise you about the Chicago Architecture Boat Tour

    During the summer months, Wendella's tours run start as early as 9 a.m., with the day's final tour not ending until 10 p.m. or 11 p.m., Scheffle said, "so if you want to come for a ride to see the ...

  23. Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

    E Monroe St & S Lake Shore Dr, Chicago, IL 60601, USA. Open in Google Maps. From the northeast corner of Lake Shore Dr. and Monroe St. follow the lakefront trail to the north and continue along the harbor's edge as the trail bends to the east. Our boat will meet you along the Monroe Harbor wall east of the cement pier (aka the pump out dock).

  24. Chicago Boat Show, a McCormick Place staple, will move to Rosemont

    January's Chicago Boat Show was expected to attract about 40,000 visitors from Illinois, Michigan, Indiana and southern Wisconsin. Exhibitors displayed some 400 fishing boats, deck boats, ski ...

  25. Everything we know about D23: The Ultimate Disney Fan Event

    D23 Ultimate Fan Pass 3-Day Ticket includes a 3-day assigned seat for evening shows at the Honda Center and 3-day access to all experiences at the Anaheim Convention Center-starting at $297/ticket ...

  26. 45-Minute Chicago River Architecture Tour from Magnificent Mile

    45 minutes. Mobile ticket. Offered in: English. Chicago Architecture River Cruise. Chicago Architectural River Cruise. Educational Tour and Sail Aboard Chicago's Official Flagship Windy 148' Schooner. from $39.00. Chicago, Illinois. Small-Group Sightseeing Boat Tour in Chicago.