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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

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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.

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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.

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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.

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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...

Tour the Windy City from the water

See the skyscrapers, hear the history, and take a tour of the incredible city of chicago with shoreline sightseeing., take a tour.

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What tour are you interested in?

Architecture River Tour

Architecture River Tour

i More info

Skyline Lake Tour

Skyline Lake Tour

Chicago CityPass

Save 48% at 5 top attractions

Where would you like to leave from?

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Michigan Ave

Michigan Avenue

401 N. Michigan Ave

Please select Navy Pier. (Skyline Lake Tours are unavailable from Michigan Avenue.)

Navy Pier

600 E. Grand Ave

124 N. Streeter Drive

When would you like to go?

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Note: Fireworks tours available Wednesday and Saturday evenings in the summer.

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Most popular tours

Your chicago adventure awaits.

Photo of Shoreline Sightseeing boat on the Chicago River

Architecture River Tour

View over 40 Chicago landmarks on our Architecture Tour as you listen to our expert guides tell you how Chicago’s buildings and engineering made the city famous.

Overhead view of Navy Pier

Skyline Lake Cruise

See the city of Chicago as you’ve never seen it before on our classic Lake Michigan boat tour that leaves from Navy Pier and offers majestic skyline views.

Navy Pier Fireworks show, with Navy Pier at night in the foreground

Fireworks Cruise

Throughout the summer months, enjoy the Navy Pier’s spectacular Firework’s show from the water with Shoreline. Tours depart every Wednesday and Saturday evening from Memorial Day to Labor Day.

sailboat tour chicago

Sightseeing in Chicago? Chicago CityPass saves 48% on premier admission tickets  to Chicago’s top 5 attractions, including the Architecture River Tour.

The reviews are in

Now in its 83rd season, Shoreline Sightseeing operates Chicago's largest and most diverse fleet of cruise boats and water taxis with 11 major tour vessels and 7 water taxis.

(312) 222-9328 ext. 1 [email protected]

  • Architecture River Tour
  • Skyline Tour
  • Fireworks Tour
  • Water Taxis
  • Accessibility Information

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
  • 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

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.

From this article

Chicago Architecture Center

Tours & Attractions

Chicago architecture center.

Mercury, Chicago’s Skyline Cruiseline

Mercury, Chicago’s Skyline Cruiseline

Shoreline Sightseeing Company

Shoreline Sightseeing Company

Streeterville

Free Spirit Yacht Cruises

Special Event Venues

Free spirit yacht cruises.

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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The Salty Dog Sailing Co.

START YOUR Chicago sailing adventure today!

Opening weekend may 18, 2024, the salty dog sailing co..

Since 2015, The Salty Dog Sailing Co. has been a premier provider of private Chicago sailing charters.

Whether you’re new to town, just visiting or a Chicago native, we invite you aboard “Peony”, our acclaimed Dufour 325 Grand Large , to experience the serenity, joy and excitement of authentic Lake Michigan sailing.

Designed by renowned Italian naval architect Umberto Felci , the premium Dufour brand, known for fine lines, ease-of-sail, and polished interiors – delivers elegance and performance in a celebrated 33′ package.

The safety and comfort of your party is our highest priority and we respond quickly to your questions.

Please click Book Now to start planning your private Chicago sailing adventure today!

Claire Forrest

All Charters Are Private Events

Charter rates.

2 Hour Charter w/Paid Captain

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Great for a Date / Proposal

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Perfect Size for Summer Fun

Spread Out and Enjoy

Big Family / Party Size

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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

How do we determine the cream of the crop? Our staff picks combine the top, most recent reviews with some of our personal favorites to make sure you get the best deal on the web. Throughout this article, you may notice some affiliate links – these have no influence on our editorial content – we pinky swear. 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.

https://media.timeout.com/images/106037667/image.jpg

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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sailboat tour chicago

ON A BOAT SAILING

Private sailboat charters in chicago, what makes  on a boat sailing different.

We're a one boat, one captain operation sharing our passion for sailing with our customers. Our Chicago sailboat charters & cruises have been enjoyed by thousands of guests since our first private charter in 2018. As we enter our 7th season, we pride ourselves on offering a safe & unforgettable way to experience Lake Michigan.

sailboat tour chicago

Captain Greg & 1st Mate Cait

Our crew have a combined 25 years sailing experience, allowing us to curate the best possible experience for our guests. Sit back & relax as you take in the sights & sounds of Chicago's famous Lakefront.

2003 Jeanneau Sun Odyssey 37

S/V Dragonfly was built for day cruises & entertaining. Our 37' luxury sailboat is a fantastic venue for any special occasion. We are a fully-licensed commercial passenger vessel and operate under the highest safety standards monitored by the US Coast Guard.

sailboat tour chicago

Learn more about the crew & S/V Dragonfly here .

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Simply the best escape from hot summer days in the city. Discover the world of sailing on Lake Michigan!

Our focus is on curated experiences for small groups of up to 10 guests that prefer the privacy & flexibility of their own Chicago sailboat rental to explore and indulge in the beauty of being on the water along Chicago's Lakefront. 2024 bookings are available Wednesday, Friday, Saturday & Sunday from Memorial Day weekend to mid-October with multiple departures daily from centrally-located Monroe Harbor in Downtown Chicago. Please visit our all charters page to learn more about our one-of-a-kind sailing adventures. Chicago is the best place to combine the thrill of sailing with views of a world class skyline- let us show you. Cheers! Captain Greg & First Mate Cait

sailboat tour chicago

OVER 500 PRIVATE CHARTERS IN CHICAGO SINCE 2018

Our  cruises & charters, now booking - summer 2024, chicago lakefront cruise.

USCG Captain 

Up to 10 Guests

This 3-hour sailboat cruise will take you & your guests on a favorable sail down the gorgeous coastline of Chicago's lakeshore, giving a unique perspective on the city's world-class architectural landscape. If you're looking for a private & intimate sailing experience Chicago - this is the cruise for you.

Starting at $899 for 6 guests

WED • FRI • SAT • SUN 10am-1pm, 1:30pm-4:30pm, 5:30pm-8:30pm

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Skyline Sunset Cruise

Relax and enjoy a captained sunset cruise on our sailing yacht, a Jeanneau Sun Odyssey 37. We will cast off from Monroe Harbor in downtown Chicago and set sail to a favorable course on Lake Michigan. Bring your own food and drinks, listen to your favorite music, and take in the views of our city’s iconic skyline from the Lakefront.

Starting at $899 for 6 guests 

FRI • SUN 6:30pm-8:30pm

Sail & swim playpen charter.

USCG Captain

Chicago's famous lakefront party is back. This 4-hour private sailboat charter is designed for you & your friends to party in luxury. We will depart from Monroe Harbor, with a good mix of adventure sailing on Chicago's Lakefront along with dropping anchor at the Playpen or a private area of your choosing. Whatever you do - don't forget a bathing suit, some sunscreen & something cold to sip on!

Starting at $1,099 for 6 guests 

Fri • sat • sun 10am-2pm, 2:30pm-6:30pm.

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Navy Pier Fireworks Cruise

This 2.5 hour Chicago sailboat cruise will split your time us between sailing the city's famous Lakefront & eventually making our way to the famous Fireworks show at Navy Pier. These are the best seats you can possible have for a world-class fireworks show. We've all seen fireworks - you've never seen anything like this before.

Starting at $799 for 6 guests 

Wed  7pm •   sat  8pm.

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“I rented [Dragonfly] to celebrate my bday with 6 close girlfriends. Greg was very communicative before the trip. He answered all my questions in a very timely manner. The boat is very spacious!

Dyna, Chicago, IL

PLAN YOUR CHICAGO SAILING ADVENTURE TODAY!

Enjoy world-class sailing, Great Lakes swimming & luxury amenities with your crew of up to 10 guests.

chicago sailboat

STEP ABOARD Be first for private sailing offers & special event  happenings on Chicago's famous Lakefront.  

Welcome to the crew!

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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!

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)

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[email protected]

sailboat tour chicago

CHICAGO'S TOP BOAT 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 sailboat & yacht 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.

boat rental chicago reviews

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.

sailboat tour chicago

773-236-724 5

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MAILING ADDRESS

400 West Belmont Harbor Drive, Chicago, IL 60657

a group of women sitting on the back of a boat rental in Chicago

773-236-7245

Belmont Harbor

Directions →

Dusable Harbor

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’s Best 90-Minute Architecture Boat Tour

Photo of Chicago’s Best 90-Minute Architecture Boat Tour - Chicago, IL, US. Hillary our tour guide

Review Highlights

chicago-s-best-90-minute-architecture-boat-tour-chicago photo XV9JSveJZLJw9r_b-B2Vag

“ Hillary was so fun and made coming all the way down to the south loop worth it. ” in 4 reviews

Lindsay A.

“ HIGHLY recommend going on this when visiting. ” in 2 reviews

Dan S.

“ Our tour guide, Billy , was super-informative and entertaining! ” in 2 reviews

Location & Hours

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Map

River City Marina - Summer Of George

900 S Wells St

Chicago, IL 60607

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Brian H. said "So let me just start off by saying if you can only do one thing while in Chicago let this be it. I was a little hesitant about spending $35.50 for an adult for a 90 minute excursion but in the end I would've sieve $50. Not only was…" read more

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Photo of Bricelyn P.

Went on the 10am tour and the weather was perfect. Both sides of the boat had amazing views! Hillary was funny and engaging. We got to see more parts of the river than I excepted and the 90 minutes was so worth it!!

sailboat tour chicago

Hillary was a great tour guide keeping it light and humorous. No script, but her knowledge of the buildings and Chicago in general was phenomenal. It's probably our third time over the years but the most memorable. A great tour to do every few years.

sailboat tour chicago

Our tour guide, Billy, was very informative and entertaining! We learned a lot about the history of Chicago and it made my partner and I appreciate the city we were visiting more.

Skyline of Chicago

Skyline of Chicago

sailboat tour chicago

Had a wonderful time on this tour. Sean was a fantastic guide, and I learned a lot about Chicago and its marvelous architecture. I liked that the boat wasn't too big or crowded. Highly recommend!

View of Chicago skyline from boat

View of Chicago skyline from boat

Summer of George at dock

Summer of George at dock

Photo of N.F. P.

Wife and I enjoyed a wonderful 90 min trip with @toursandboats enjoying the architectural beauty of Chicago on the Chicago River. Took some amazing photos from the uncrowded bow of the boat; the other passengers on board were all very chill and the staff were fantastic including the captain with his dry sense of humor! The boat was clean and well maintained, in particular the bar was very well maintained and made the trip even more enjoyable. Will definitely repeat another trip with these folks next time I'm in Chi-Town, but I'm gonna try to do an evening cruise which may be even more amazing. Don't hesitate, book with this crew and you'll have a great time.

sailboat tour chicago

See all photos from N.F. P. for Chicago’s Best 90-Minute Architecture Boat Tour

Photo of Shelley A.

What a wonderful day! The tour was awesome. Lots of fun information about the City.I would highly recommend it. The weather was kind of cloudy but at least it didn't rain and no sun damage.

Photo of Jess G.

Booked tour through Groupon. Our tour guide Teela was so great and fun. Had such a great time and learned a lot!

sailboat tour chicago

I've taken several boat tour of Chicago, and this is the best by far! Our tour guide, Billy, was super-informative and entertaining! Very comfortable boat with a full bar. Great outing in Chicago!

Photo of Allison K.

This was well worth it. The captain (Joe) and the guide (Dave) were friendly, inviting, and made the tour wonderful. Something I would do again on my next visit.

Photo of shalini t.

I had an excellent experience with Tours and Travels! Initially, I faced some challenges reaching them over the phone, but their customer service team truly impressed me. They not only resolved my issues but went above and beyond to assist me. Their dedication to customer satisfaction is outstanding. I highly recommend booking your tickets directly with them for a seamless and stress-free experience. Kudos to Tours and Travels for their exceptional service!

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Boat show in Illinois voted one of the best in the country in USA TODAY poll

sailboat tour chicago

A recent USA Today readers’ poll has determined that Illinois can boast one of the top boat shows in the United States.

USA TODAY determined the top shows by asking a panel of experts for nominations. Readers then voted on the top picks and named the Discover Boating Chicago Boat Show as the fifth-best event of its kind in the country.

“In addition to the vessels for sale, live music, cook-offs, a trout pond, a kids’ corner, and an antique and classic boat display make this event a standout,” USA Today wrote in the winning entry .

USA Today announced the winners May 8.

USA TODAY 10best: NASCAR track in Illinois voted one of the best in the country

Top boat shows according to USA Today Readers’ Choice

  • St. Petersburg Power and Sailboat Show , St. Petersburg, Fla.
  • Palm Beach International Boat Show , West Palm Beach, Fla.
  • Detroit Boat Show , Detroit, Mich.
  • Fort Lauderdale International Boat Show , Fort Lauderdale, Fla.
  • Discover Boating Chicago Boat Show , Chicago, Ill.

sailboat tour chicago

Vote Tall Ship Windy for USA Today's 10 Best - Best Boat Tour. Click to vote!

Tall Ship Windy

  • Great for Children!

Educational Sail: Tall Ship Discovery Sail

Quick Details

  • Hour Glass Duration: 90 Minutes
  • User Ages: All Ages
  • Calendar Availability: Saturdays, Sundays & Mondays
  • Sailboat Sail: Weekend Things to Do in Chicago
  • Map Marker Departure: Chicago's Navy Pier

A Learning Adventure on Lake Michigan

Ahoy! Join us for an exciting educational adventure aboard Tall Ship Windy! Great Lakes history and maritime tradition come alive from the decks of our floating classroom with Windy’s Tall Ship Discovery Sail (TSDS).

This unique, hands-on learning experience is a great way to enjoy physics, history and storytelling while taking an active part in sailing the vessel. Share the marvel of maritime heritage on the Great Lakes as history comes alive with an exciting educational adventure for curious minds of all ages. Join a group on their sail training mission for hands-on sailing aboard Windy and then muster for learning stations led by our crew-educators. This is approximately a 90-minute sail.

Watch as faces light up with excitement as we turn theory into practice, have real fun and are educated along the way.

  • Chevron down Add-on Trip Insurance

$8.00 Per Guest | Add to your ticket at checkout

Trip insurance allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time. Refunds for cancelled charters are less the $8.00 cost of insurance and 3% booking fees.

General Admission tickets without trip insurance may only change or cancel a reservation and receive a refund up to 48 hours before their scheduled sail time.

  • Chevron down Cancellation Policy
  • RAIN OR SHINE EVENT: In the unlikely event that your tour is cancelled, you may exchange your ticket for another day or receive a refund.
  • No-shows will not be eligible for rescheduling or refund. Guests must arrive at least 30 minutes before the scheduled departure time or risk forfeiture.
  • The Captain reserves the right to postpone a sail for up to 15 minutes in the case of passing inclement weather.
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Business | Chicago Boat Show setting sail for Rosemont in…

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Business | Chicago Boat Show setting sail for Rosemont in 2025

Workers pull the protective wrapping off a Carver C52 Coupe yacht as preparations continue for the Chicago Boat, RV & Sail Show at McCormick Place in Chicago on Jan. 4, 2018. (Terrence Antonio James/Chicago Tribune)

The annual show, which has seen dwindling attendance in recent years, is relocating to the northwest suburbs after nearly a century in Chicago, in part to be closer to its target recreational boat-buying customer, organizers said.

“We met with our exhibitors and the decision was made that we need to go out to the suburbs,” said Darren Envall, manager of the Chicago Boat Show. “It is closer to where people are doing boating in the Fox Lake area as well as Lake Geneva, and it is closer to where the dealers are located.”

The show, which dates back nearly a century, has throughout its history been a Chicago event of national importance on the boating industry calendar.

Owned and operated by the National Marine Manufacturers Association, the show was a mainstay at McCormick Place for decades, and before that at the since-demolished International Amphitheatre. The show has gone through several incarnations, reaching its pinnacle in the 1990s as the Chicago Boat, Sports & RV Show, which regularly attracted more than 50,000 visitors each year.

While attendance had declined in recent years, it still drew about 40,000 visitors annually before temporarily shutting down in 2021 and 2022 during the pandemic.

The most recent five-day show in January, hampered by a heavy snowstorm, drew fewer than 20,000 attendees, Envall said.

A loss for McCormick Place, a win for Rosemont, the migration of the boat show represents something of a zero-sum game for the Chicago-area convention business, which has been recovering in the post-pandemic landscape.

“Big exciting news,” said Christopher Stephens, executive director of the Donald E. Stephens Convention Center.

While there had been discussion in the past about luring the boat show to Rosemont, Stephens said things got “more serious” this year, helping the northwest suburb land a major regional event.

Stephens said the Rosemont convention center offered the boat show and its attendees adjacent hotels, entertainment and a 9,000-space parking facility, all of which helped seal the deal. Down the road, the show could expand to the entire 840,000 square feet of exhibition space, as needed.

He also touted safety as an advantage for Rosemont over Chicago, which has struggled with the perception of increased crime in the wake of the pandemic.

“We always want to make sure when people come here that they feel safe,” Stephens said. “We provide as much policing and traffic controls as possible for attendees.”

While corporate meetings are still down, Stephens said conventions and large public events have returned to pre-pandemic levels in Rosemont, with the 2025 calendar now significantly bolstered by the addition of the boat show.

At the same time, he said Rosemont doesn’t try to “poach business” from Chicago.

“We’ve always thought that a strong McCormick Place was good for Rosemont,” Stephens said. “We’ll obviously never turn down an event, if they want to relocate out to Rosemont and we can accommodate them, but we don’t actively solicit.”

For McCormick Place, it’s been win some, lose some in March.

Earlier this month, Microsoft announced it was returning its Ignite information technology conference to McCormick Place in November after a nine-year absence. The inaugural event in 2015 drew 20,000 attendees to Chicago’s convention center.

“The sales cycle can be very dynamic in the convention industry,” said Cynthia McCafferty, a McCormick Place spokesperson. “Microsoft Ignite was a great addition to our calendar this year, we have a very robust pipeline of new business ahead and feel good about the future.”

The loss of the boat show is both symbolic and substantial for McCormick Place, erasing a solid and historically well-attended event from the January calendar in 2025, and likely beyond.

The Chicago Boat Show was often the first big public event of the year, setting the table for the annual Chicago Auto Show and filling the exhibition halls with visitors dreaming of summer during the coldest winter months.

In 2025, the Chicago Boat Show will keep the city’s name, at least for now, as it migrates to the suburbs for a scheduled Jan. 8-12 run.

The new version of the show will focus more on fishing boats and weekend warriors who hitch up a trailer and head for the Chain O’Lakes to drop a line, as opposed to plying Lake Michigan in larger crafts. Envall said that represents about 85% of the boaters in the Chicago area, most of whom reside in the suburbs.

Despite its long history in Chicago, Envall said he expects Rosemont to be the event’s home for years to come.

“There’s a time to change and the change was to get out to the village of Rosemont where more of the recreational boater is reflected in the market,” Enval said.

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