yacht rides in chicago

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City Cruises

Explore Chicago from a unique vantage point—the water! Enjoy a brunch, lunch, or dinner cruise with fresh chef-prepared plated or buffet meals, live DJ entertainment, dancing, rooftop games, and amazing Chicago skyline views. You can also embark on a thrilling Seadog speedboat ride and explore iconic landmarks on a narrated architecture tour or catch speed on a lakefront speedboat tour.

Our yachts are the ideal venue for any celebration—a vacation excursion, romantic date night, holiday gathering, birthday party, anniversary dinner, company event, school trip, or even your dream wedding. Book today and elevate your next occasion with unbeatable views of Chicago from Lake Michigan or the Chicago River.

Holiday Cruises    Architecture & Speedboat Tours   Brunch & Lunch Cruises   Dinner Cruises

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Signature Bottomless Mimosa Brunch Cruise

Elevate your weekend plans with a one-of-a-kind brunch on the water!

Premier Bottomless Mimosa Brunch Cruise

You'll indulge in a chef-prepared buffet meal, bottomless mimosas, and breathtaking city views.

Chicago Signature Lunch Cruise

Upgrade your lunch with family or friends to a chef-prepared buffet and views of Chicago’s landmarks.

Early Signature Dinner Cruise

Spend your evening on Lake Michigan with dining, picturesque views, dancing, DJ entertainment, and an assortment of games.

Chicago Signature Dinner Cruise

Turn your dinner into an incredible night out with a delicious chef-curated buffet for all ages, and breathtaking city views.

Chicago Premier Lunch Cruise

You’ll be treated to a chef-prepared plated meal, and creative cocktails while a live DJ sets the mood.

Chicago Premier Dinner Cruise

This upscale evening on Lake Michigan features a chef-prepared plated meal, craft cocktails, and exceptional service.

Seadog River & Lake Architectural Tour

Soak in unobstructed views of Chicago’s famous architecture cruising along the skyline at top speed!

Seadog Lakefront Speedboat Tour

Buckle up for Lake Michigan’s most iconic thrill ride with a Seadog Lakefront Speedboat Tour!

Seadog Extreme Thrill Ride

Get ready for pure exhilaration as the Seadog dares full 360-degree spins, hairpin turns and twists, and full-throttle slalom runs.

Chicago River Cruises

Explore a variety of cruises that set sail from the River Esplanade City Cruises location at 455 N Cityfront Plaza Drive.

Holiday Cruises

Chicago Seadog Haunted River Tour

Embark on a boat tour that explores Chicago's spooky past while winding through some of the city's most gorgeous architecture.

Sherman & Tingle Halloween Cruise with 97.1 The Drive

Hosted by your favorite radio duo, this costume cruise promises a night of thrills and chills.

Thanksgiving Day Signature Afternoon Lunch Cruise

Gather with loved ones aboard our Signature Chicago Thanksgiving Lunch Cruise for a picturesque afternoon of togetherness, turkey, and all the trimmings!

Thanksgiving Day Premier Afternoon Lunch Cruise

A gourmet feast of turkey and all the trimmings will be complimented by festive cocktails and captivating panoramas of Chicago’s iconic architecture.

Christmas Eve Premier Brunch Cruise

Indulge in a delicious buffet featuring savory and sweet holiday classics, bottomless mimosas exceptional service, and breathtaking views of the skyline.

Christmas Eve Premier Dinner Cruise

This festive evening on Lake Michigan features a delicious plated meal, specialty seasonal cocktails, and exceptional service.

Christmas Day Premier Brunch Cruise

Indulge in a delicious buffet featuring savory and sweet holiday classics, bottomless mimosas, exceptional service, and breathtaking views of the skyline.

Christmas Day Premier Dinner Cruise

New Year's Eve Signature Brunch Cruise

Come together for unparalleled festivities with dining, dancing, and magnificent skyline views on Lake Michigan.

New Year's Eve Signature Dinner Cruise

Come together for unparalleled festivities with dining, dancing, and magnificent skyline views lit up by the dazzling fireworks display over Lake Michigan!

New Year's Eve Premier Dinner Cruise

Count down to 2025 with the ultimate on-the-water party: the Premier Chicago New Year’s Eve Fireworks Dinner Cruise on Lake Michigan!

New Year's Day Premier Brunch Cruise

Savor an unforgettable start to the new year with a brunch cruise filled with delicious craft cocktails, plated, chef-prepared menus, and top-notch service.

Architecture & Speedboat Tours

Brunch & Lunch Cruises

Dinner Cruises

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

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

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

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

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

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

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

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

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

Tours & Attractions

Chicago architecture center.

Mercury, Chicago’s Skyline Cruiseline

Shoreline Sightseeing

Streeterville

Special Event Venues

Free spirit yacht cruises.

Urban Kayaks

River North

Wendella Tours & Cruises

The Magnificent Mile

Chicago’s First Lady Cruises

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Architecture River Tour

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• 75-minute, guided boat tour
• Unique views from the water create an entirely new perspective of the city
• 40+ landmarks including the Tribune Tower, the Wrigley Building, and Marina City

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• 45-minute cruise on Lake Michigan
• Stops on the North and South side of the lake front for two iconic skyline photo ops
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Sightseeing in Chicago? Chicago CityPASS ® saves 48% on premier admission tickets  to Chicago’s top 5 attractions, including the Architecture River Tour.

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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.

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The 15 best boat tours in Chicago

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

Step up your sightseeing game by taking things further than street-level with these top boat tours in Chicago. Swap a walk along Michigan Avenue and State Street with a relaxed ride across the water, where there's no chance of taking a wrong turn.  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 .

From architecture tours and history lessons to straight-up  sightseeing affairs , romantic sunset excursions and pirate-themed family fun, there's a Chicago cruise for every groove. 

RECOMMENDED: 📍 Find more to explore with the best things to do in Chicago 🏨 Plan your trip with the  best hotels in Chicago 🍹 See more views from the best rooftop bars 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 .

Been there, done that? Think again, my friend.

Best Chicago boat tours

1.  1.5-hour guided architecture river cruise.

Best for  panoramic views 

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.  

2.  Seadog River and Lake Architectural Tour

Best for  design geeks

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 Chicago River cruise has finished traversing the waters, 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.

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

Best for families

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. 

4.  1.5-Hour Romantic Sunset Cruise

Best for a romantic 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.

5.  Tall Ship Windy Architecture & Skyline Sailing Tour

Best for an informative sailing trip

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.  

6.  Seadog Speedboat Tour

Best for adrenaline junkies

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. 

7.  Lake Michigan Skyline Sightseeing Cruise

Best for skyline views

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 this Chicago architecture tour 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. 

8.  Lake Michigan Gourmet Dinner Cruise

Best for dinner and dining  

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.

9.  Chicago's Lake Michigan Kayak Tour

Best for the outdoorsy type

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.  

10.  Lake Michigan Buffet Brunch Cruise

Best for brunching - as long as you don't get sea sick that is.

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. 

11.  Lake Michigan Odyssey Gourmet Lunch Cruise

Best for a cute date night 

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.  Lady Grebe Chicago River Experience

Best for small groups

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.

13.  Chicago Electric Boat Company Tour

Best for a casual cruise 

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.

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

Best for an iconic vessel

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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Downtown Chicago street closures due to the Chicago Marathon extend through 6 pm Sunday 10/13. Please allow extra travel time.

Evening River Cruise

Join us when we open for St. Patrick's Day weekend! Tickets on sale now!

Experience our renowned Chicago Architecture Center River Cruise in the glow of the setting sun. Serene and bathed in a softer light, the city's architecture takes on a whole new life as it begins its transition from day to night. Savor the views with friends and family as you enjoy a relaxing evening on the water with cocktail in-hand. 

View Route   Buy Tickets

General Boarding Tickets Start At

Ticket details.

• Priority Boarding tickets start at $74 and include exclusive early boarding period, skip-the-queue during general boarding, and Chicago Architecture Center admission
• General Boarding tickets start at $59. Include a visit to the Chicago Architecture Center for just $5 more!
• Tickets can be purchased online , in-person at our dock during regular season hours or at the Chicago Architecture Center. Avoid the box office by choosing "eTickets" or "Print at Home" as your delivery method. 
• Tour departures frequently sell out. Reserve your tickets in advance to avoid disappointment.
• Select "Will Call" to pick up your tickets at our dockside ticket office; bring your confirmation number.
• Each person must have a ticket including infants and children.
• Prices are subject to change.

Full Schedule

Early Spring March 17 - April 25

Late Spring April 26 - May 23

• Mon 7:00 pm
• Thu 7:00 pm
• Fri 5:30 pm 7:00 pm
• Sun 6:00 pm

Summer May 24 - October 14

• Mon 5:30 pm 7:30 pm
• Tues 7:00 pm
• Wed 6:00 pm
• Thu 5:30 pm 7:30 pm
• Fri 5:30 pm 7:00 pm 7:30 pm
• Sun 5:30 pm 7:30 pm

Early Fall October 15 - November 3

• Sun 5:30 pm 6:00 pm

Late Fall November 4 - November 24

2024 Evening River Cruise season begins April 26th and extends through November 24th. Tickets on sale now!

We are located at Michigan Ave and Wacker Drive, Chicago IL.

Tour Details & Tips

• Tour Duration 90 minutes
• Arrival Time Make sure your entire party arrives 30 minutes prior to departure.
• Priority Boarding Tickets include exclusive early boarding period, skip-the-queue during general boarding, and Chicago Architecture Center admission.
• General Boarding Tickets begin boarding approximately 15 minutes before departure.
• Seating Open outdoor seating is guaranteed for all guests. The number on your ticket does not represent a seat number.
• Tour Route The tour travels all three branches of the Chicago River. View tour route map. Tour route subject to change without notice.
• Cruises depart rain or shine. Tickets may not be refunded or exchanged if you miss your boat - allow extra time!
• What to Bring Your sunglasses, cap or visor, as the sun can interfere with your view of the buildings.
• Parking Discounted parking available at 111 E. Wacker Drive with proper validation from ticket office. Visit our  Location page  for more.
• Did you know?  A portion of your ticket fee supports the educational work of the Chicago Architecture Center!

Amenities & Accessibility

• Full-service Bar/Snack Bar  A full-service bar and snack bar are available on every vessel.
• Outdoor Seating Each vessel features an open-air upper deck to enjoy Chicago's architecture safely outdoors.
• Well-Appointed Restrooms  Well-appointed restrooms are available on each vessel.
• Free Stroller Storage  Strollers will be folded and stored in the salon during the cruise. Children must be removed from strollers before boarding.
• Limited Mobility Services Available  See our  Location page  for river-level drop-off directions for guests with accessibility needs. Our staff is also available to provide early boarding services for those with limited mobility.

Photo Gallery

Frequently Asked Questions

• Is there a bar and food onboard?
• Yes. All boats have a full bar available onboard with cocktails, wine, craft beer, water, cold brew and more, as well as locally sourced snacks available for purchase.
• What sets your tours apart from the others?

We are the only tour that partners with the Chicago Architecture Center to offer the official Chicago Architecture Center River Cruise aboard Chicago's First Lady. All of our tours are given by experienced, volunteer docents who receive hundreds of hours of training from the Chicago Architecture Center before guiding the river cruise tour.

• How long is the tour?
• Each tour is 90 minutes.
• Do I need to buy tickets in advance?

Advance reservations are recommended as many tours sell out.

• Is there assigned seating?

All seating is general admission, though proper distancing measures are put in place to ensure the safety of each party outside of their own groups, per city ordinances. There is enough seating for all guests to have a seat outside. While seat numbers are printed on the tickets, you can ignore these as they are not valid.

• Do I have to print my tickets?
• You do not have to print your tickets. You can show your mobile ticket to our dock attendant with your smartphone, or you can have your tickets printed at the dockside will call window (be sure to bring a photo ID and your confirmation number).
• Does the boat go on the lake?

No, the tour is only on the Chicago River. If you’d like to take a lake tour, please check out our sister cruise line Mercury, Chicago’s Skyline Cruiseline .

• Are there restrooms onboard?

Yes, all the boats have restrooms onboard. There are also wheelchair accessible bathrooms on the Classic Lady, Leading Lady, and Emerald Lady. Please note: the restrooms close 15 minutes before the end of the tour for safety reasons.

• Can I bring luggage onboard?
• Due to security reasons, luggage cannot be brought onboard. There is not an area to store your luggage dockside either. We recommend having your hotel hold your luggage.
• Can I bring a stroller onboard?
• Yes, you can bring a stroller onboard. Children must be removed from strollers before boarding. Strollers will be folded and stored in the salon during the cruise.
• Are there changing tables onboard?

The Classic Lady, Leading Lady, and Emerald Lady have changing tables onboard in the family restroom. The Little Lady, Fair Lady, and First Lady do not have changing tables onboard.

• Are dogs allowed onboard?

Only service dogs are allowed onboard. Our sister company, Mercury , offers the popular Canine Cruise on summer weekends.

• How can I get to your dock without using stairs?

There are two ways to reach our dock along Chicago’s Riverwalk without using stairs: 1. On foot via the ramp located on Wacker Drive at State Street. 2. Vehicle drop-off area on Lower Wacker Drive. Visit our location page for more information.

• Can I trade my tickets for a different date/time?
• No, all tickets are nonrefundable and nonexchangeable.
• Do you cruise rain or shine?
• Yes, we cruise rain or shine. All the boats have two levels – the top deck is open-air, and the lower deck is an enclosed, climate-controlled salon. Each salon is surrounded by large windows so you can stay comfortable while still taking in the magnificent views. Tour commentary is broadcast over speakers on both levels.
• Are the boats wheelchair accessible?

Chicago's Leading Lady, Chicago’s Classic Lady, and Chicago's Emerald Lady are wheelchair-accessible. These vessels cruise at the 9am, 10am, 11am, 12pm, 1pm, 2pm, 3pm and 5pm departure times. When boarding, guests cross two ramps and enter through a 36-inch-wide opening (doorway). Crew members will assist in guiding the wheelchair across the gangway. Please present yourself to our staff if you prefer to board before general boarding starts. Guests unable to climb stairs to the upper deck may choose to sit in the open-air bow or the enclosed, climate-controlled salon with large windows. For safety reasons, motorized scooters and electric wheelchairs cannot be accommodated. Guests who are able to transfer may use the company's manual wheelchair based on availability. Visit our accessibility page for more information.

Free Spirit Private Yacht Charters

Experience all-inclusive luxury and set sail across the crystal blue waters of lake michigan., lake michigan, chicago, il, welcome aboard, whether celebrating a birthday or entertaining corporate clients, we personalize every detail of your event to provide an extraordinary experience you’ll never forget. soak in the magic of the chicago skyline. sip on refreshing cocktails and indulge in an array of delicious food. we’re thrilled to have you on board.

• Free Spirit

Our spacious Free Spirit luxury yacht accommodates up to 120 people and is custom-designed for your relaxation and comfort, inside and out. Free Spirit is perfect for larger groups for business meetings, company outings, networking events, family celebrations, weddings or parties. Whatever the occasion, it’s more memorable when it’s a boat!

• Gypsy Spirit

Our Gypsy Spirit luxury charter yacht is perfect for an intimate gathering or a small company outing. The Gypsy accommodates up to 49 passengers, offering multi-level entertaining with a salon, galley, and aft deck lounge area. Sit back, relax and cruise Chicago River or Lake Michigan.

WHAT WE Offer

We make special occasions memorable!

At Free Spirit Yacht Cruise, we go above and beyond to guarantee your occasion is truly special. You can delight out-of-state visitors with breathtaking views of Chicago’s world-famous skyline. Host a casual breakfast cruise with sparkling mimosas.

Need to impress new business clients? Break out of the ordinary and stun clients with an elegant dinner on a cruise along Lake Michigan.

From our attentive staff to the luxurious ambiance, our gorgeous yachts offer the perfect venue for you to host your next event.

Ready to Start Planning Your Event?

Free Spirit Yacht Cruises

708-361-2220

[email protected]

Burnham Harbor, Chicago, IL

Interested in chartering a yacht with us? Contact Free Spirit Cruises at 708-361-2220 or complete our online form. Let’s see how we can help you today!

Have A Question? Contact Us Today!

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Odyssey Cruise on the Chicago River

PRODUCT CURRENTLY NOT AVAILABLE FOR SALE

Imagine pairing an architecture-focused boat ride along the Chicago River with the Odyssey Cruise : the result is this divine Chicago River cruise. On this romantic adventure, you get the best of both worlds — the beauty of the buildings from Chicago’s financial sector with the comfort of an all-glass vessel with a luxury, 3-course meal aboard . Choose from a lunch or dinner cruise that includes a fantastic fireworks display over the lakefront at certain times of the year, and experience Chicago in a way you’re sure to never forget .

Pricing & Schedule - PRODUCT CURRENTLY NOT AVAILABLE FOR SALE

Lunch & brunch cruises:.

Contact us: [email protected] (opens in a new tab)

Dinner Cruises:

Activity details, meeting point:.

Odyssey Dock: Navy Pier, 600 E Grand Ave

• Live music onboard
• Lunch or dinner with a 3-course menu (excluding drinks)
• Navy Pier fireworks display (Wednesday and Saturday, during summer)
• All additional taxes and fees

Maximum Group Size:

Click the tabs to find out more, good to know, terms & conditions.

• We recommend that you arrive 40 minutes before your cruise is scheduled to depart as you’ll need to pick up your tickets before boarding the ship.
• Your tickets will be available at Odyssey Cruise box office , located right beside the boat – you can’t miss it! Just mention your name or the confirmation number we sent to you at the time of booking.

There will be no cruises available on the following dates (2020):  2/14-16, 4/12, 5/10, 6/21, 7/4, 11/23, 12/24-25, 12/31, 2/14/2021

• IMPORTANT: Once made, your reservation is not automatically confirmed. Upon receiving your request, a member of our team will purchase the ticket(s) and email them to you. In the case of no availability, your reservation will be canceled and you will be refunded the full price.
• The ticket value includes the boat trip exclusively; transportation to the boarding point is not included.
• This service has a 100% penalty for cancellation after reservation. Date and time changes will not be allowed after confirmation of purchase.
• We recommend arriving 40 minutes in advance for check-in, as the boat starts to board 10 minutes before the departure time and leaves at the scheduled time.
• These summer cruises run from May 25 to August 31. Keep in mind that not all cruises have daily departures.
• The cruise may be canceled at the last minute if the minimum number of sales required has not been met or if the boat has been chartered for a private party.
• In case of cancellation on behalf of the company, the amount paid will be fully refunded or the passenger may be offered a change in ticket for a different vessel or date .
• Chicago Travel & Tours is not responsible for damage or inconvenience caused by cancellation of the cruise.
• The fireworks show is offered by the City of Chicago and Navy Pier. The cruise company and Chicago Travel & Tours are not responsible for a refund in the case of cancellation due to the fireworks display.
• In case of a storm, the ship will be anchored at the pier, but the onboard services (shows and food) will be served normally . In this case, the customer will receive some sort of upgrade (possibly open bar), but a refund will not be possible. We are not responsible for any inconvenience caused by meteorological conditions.

Yes, please arrive 40 minutes before your cruise is scheduled to depart to allow enough time to pick up your cruise tickets and get onboard.

No, guests are responsible for arriving at the meeting point themselves. The meeting point is located at a very easy to find, popular location which, depending on your hotel location, can be reached on foot or by a short taxi ride.

Children are welcome to join all brunch, lunch, and dinner cruises.

Yes, please let us know at the time of booking as a special request, and we will do our absolute best to accommodate your dietary needs.

Yes, the Odyssey Cruise box office, located right beside the boat – you can’t miss it!

Drinks are not included on any of the cruises and must be paid for separately by the passenger.

Yes, after the cruise, the ship will dock back into the same place that it departed from.

See More of Chicago!

Chicago helicopter ride, skydeck breakfast experience, chicago citypass.

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• Architecture Boat Tours
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COVID-19 SAILING PROTOCOL >

Chicago line cruises, chicago boat tours, discover world-famous architecture from chicago’s best vantage point., chicago river architecture tour.

Cruise down the Chicago River for 90 minutes as you listen to our expert guides discuss the history, impact and legacy of Chicago's renowned architecture.

Where to Find Us

Our boats are docked on the slip of water off the Chicago River called Odgen Slip. Click here for directions.

Ticket office and boarding: 465 N. McClurg Court Chicago, IL 60611

For help with directions, call us at 312-527-2002.

Bar Service & Merchandise

Complimentary

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

BEER, WINE & COCKTAILS

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

MERCHANDISE

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

See How Guests Are Enjoying Our Tours on Instagram

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Celebrating Chicago by Boat since 1981 with River Architecture Tours | Private Boat Cruises #chicagolinecruises

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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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.

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

NASCAR parking restrictions and street closures are in effect through July 15. Click here for more information .

• Accessibility

CHICAGO BY NIGHT! Cruise

See Chicago's skyline sparkle and glow as you glide along the Chicago River and Lakefront under the dazzling glow of the city by night. 

2024 CRUISING SEASON MAY 24 - NOVEMBER 2

Tickets on sale now!

See Chicago Twinkle and Glow

Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night. Hear lively commentary as you feel the night breezes and see Chicago’s dramatic skyline transformed into a glittering jewel. Family-friendly boat tours are our specialty!

Priority boarding now available!

• Includes exclusive early boarding period • Skip the queue during general boarding

Ticket Price

• Adults (Priority Boarding) $47
• Adults (General Boarding) $42
• Kids 5-15 (Priority Boarding) $24
• Kids 5-15 (General Boarding) $19
• Under 5 Free

Call us for group reservations at 312-332-1368 or contact us at [email protected] (group rates available Sunday - Friday).

Ticket Pricing

Full schedule.

May 24 - October 14 Departing Monday, Wednesday, Thursday, Friday, Saturday, & Sunday at 8:15pm

October 15 - October 20 Departing Friday at 8:15pm

Located on Chicago’s Riverwalk

On the Chicago Riverwalk just off The Magnificent Mile

We love groups!

A fun, relaxing, informative boat tour along Chicago's beautiful waterways is the ultimate way to experience the city and leave a lasting impression on your group.

“The city lit up at night was beautiful, and our guide was both entertaining and informative. We highly recommend this tour.”

Julie G., Facebook

Frequently Asked Questions

No. Reservations are not necessary for daytime tours, though you are welcome to purchase tickets in advance online . We also encourage advance purchase online or dockside if you desire to cruise a particular date and time and want to guarantee your seats aboard.

We do advise that you buy CHICAGO BY NIGHT! and 3D Fireworks Cruise tickets in advance – online or at the box office – as these tickets are extremely popular.

Online we accept Visa and MasterCard. At our dockside ticket office, we accept cash, Visa and MasterCard.

Beverages – including water, soda, canned cocktails, beer, and wine – are available for purchase on board. Please note, no outside alcoholic beverages are allowed.

Snacks - including small items such as chips, cookies, and nuts - are also available for purchase.

Please note that all ticket sales are final.

All of our Urban Adventure Cruise, Chicago By Night! and 3D Fireworks tours pass through the Chicago River Lock System. Our guide/narrator gives a full explanation of the operation of the lock. You’ll feel the boat rise as you enter Lake Michigan and lower as you return to the River.

Yes. Our cruises depart rain or shine. We have open and covered seating on board.

Yes, of course! There are "Heads" located on board as well as one lined with newspapers for your dog(s) during the Canine Cruises.

The safety of our guests and crew is our number one priority. After more than 80 years providing memorable cruises of the Chicago River and Lake Michigan for millions of guests, we are proud to say we have a perfect safety record.

All of our vessels are regulated, licensed and inspected by the United States Coast Guard (USCG) every year, and have undergone stability testing to ensure our guests are safe on their waterway experience. Our captains and deckhands go through an extensive training and drilling program that goes above and beyond the standards set by the USCG. Because we are committed to continuing education, we provide extra training every day to our crew.

If you have any questions about our safety training protocols or other concerns, please contact our Company Security Office Captain Tom Hacker at [email protected].

No. Luggage is not allowed aboard the Mercury vessels. Please leave your luggage at your hotel or check your bags in at a hotel near the dock (be sure to confirm in advance the ability for the hotel to accommodate you). Also, please be aware that all bags (purses, backpacks, etc.) are checked before boarding.

Yes, strollers may be brought aboard and will be folded and stored in the indoor salon for the duration of the cruise. They are not allowed on the deck. Please note, children must be removed from strollers before boarding.

In accordance with ADA guidelines, we welcome service dogs onboard. The service animal must be harnessed, leashed, or tethered while in public places unless these devices interfere with the service animal's work or the person's disability prevents use of these devices. Emotional support animals, pets and other animals not covered by the ADA are not permitted. All dogs are welcome on  Mercury's Canine Cruise ! Please visit the ADA's FAQ on service animals for further details. 

We love groups and would be happy to offer you a group discount if you would wish to reserve in advance! Please call 312-332-1368 or [email protected] for more information! 

Please note that we do not offer group discounts for our 3D Fireworks Cruise, but are happy to make a group reservation for full price! 

Boarding begins 15 minutes prior to scheduled departure time. Choose any seat - all offer a great view!

Children under 5 are always welcome free of charge, but do still require a ticket. Folded strollers may be brought on board. Children’s rates available for kids 5-15 years old.

At this time the Riverwalk does not offer any elevators. For those who need ADA ramps, you may access the Riverwalk via the ADA ramp at State Street and Wacker Drive within the Vietnam Memorial Park. Then just follow the Riverwalk to the East under the Michigan Avenue Bridge. Our Ticket Office is marked with a blue awning. Our stairway offers handrails, and shade from the sun. For guests needing special vehicle drop-off assistance, click here for Mobility Assistance directions.

For safety reasons, motorized scooters and electric wheelchairs cannot be accommodated aboard the ship. Guests who can transfer may use the company's manual wheelchair, based upon availability. Please note guests using manual wheelchairs must be accompanied by individuals who are capable of assisting/lifting the wheelchair over the boat’s threshold. Under Federal law and due to special marine safety construction guidelines, USCG-regulated small vessels are not subject to land-based architectural configuration requirements. Although we do our best to accommodate passengers with limited mobility consistent with our vessel capabilities, staffing and the docking space which is publicly owned and controlled, we can do a better job with advance notice .

LAZ Parking Garage at 111 E. Wacker Drive. This garage is across the street from our street-level dock entrance. Make a self-parking reservation online .

Discount rates available for Mercury customers with validation: $14 for 1-3 hours or $15 for 3-4 hours of parking. After 4 hours, standard rates apply. IMPORTANT: You must have your parking ticket stamped at our ticket window or on your boat in order to receive the discounted rate. Stamped tickets must be further validated at the parking garage office before departing the garage. Note: LAZ Parking Services at 111 E. Wacker is not owned or affiliated with Chicago’s First Lady Cruises. The parking information posted here is merely for the convenience of our guests and is not to be construed as a recommendation or endorsement.

We are located on Michigan Avenue just 3 blocks north of Millennium Park. Visit TheMagnificentMile.com or MillenniumPark.org for activities, events and special offers.

• City Tours >
• River Cruise

CAC River Cruise aboard Chicago's First Lady

Led by the Chicago Architecture Center's expertly trained docent volunteers, this 90-minute cruise reveals fascinating stories behind Chicago's majestic buildings in a way no other tour can.

Northeast corner of Michigan Ave. and E. Wacker Dr ( 112 E. Wacker Drive ). Look for the black awning marking the stairway entrance. Arrive 30 minutes prior to your cruise departure time. Allow extra time for traffic and parking in summer.

Tour Highlights

Rated #1 year after year.

Learn about the architects who created our city's magnificent buildings—and the stories behind them. Along the way, you'll also hear how Chicago grew from a small settlement into one of the world's largest cities.

This classic tour, aboard the city's most luxurious fleet, is a must for out-of-town visitors and Chicagoans alike.

Boat Amenities

About Our Boat Partner

Evening River Cruise

Serene and bathed in softer light, the city's architecture takes on a whole new life in the setting sun. Wind down and enjoy a cocktail with friends and family on our luxury boats. All departures later than 5:00 p.m.

Tour Information and Tips

• Each person must have a ticket, including infants and children. Please note that infant tickets must be purchased with an adult ticket.
• Seating is general admission.
• All tours depart rain or shine. Climate-controlled cabin is available.
• Arrive 30 minutes prior to your cruise departure time. Allow extra time for traffic and parking in summer.
• Cruise guests board 15 minutes before departure time.
• Tickets may not be refunded or exchanged if you miss your boat. Allow extra time.

Accessibility

Chicago’s First Lady Cruises works hard to ensure that everyone is able to access the beauty of their boats and enjoy a wonderful experience aboard. For the best experience, give us advance notice for any special boarding needs.

Guests with Limited Mobility – What to Expect Onboard

Handicap Accessible Boats

All our boats, except Chicago's First Lady & Chicago's Little Lady, are handicap accessible and offer a wheelchair-accessible restroom.

Seating Options

Guests who are unable to climb stairs to the upper deck may sit on the open-air bow deck or the climate-controlled cabin with large windows.

Accessing the Dock Area

For guests unable to use stairs, there are two options: an ADA-compliant ramp to the Riverwalk at Wacker Drive and State Street, or a drop-off area on the same level as our dock at Lower Lower Wacker Drive. View directions .

Assistance can be provided

Staff members will gladly take table-side drink orders for passengers with limited mobility.

Have more questions?

Please visit Chicago's First Lady or contact our tour operations team.

How to Buy Accessible Tour Tickets

Tickets for tours on accessible boats can be purchased by selecting the 10 a.m., 11 a.m., 12 p.m., 1 p.m., 2 p.m., 3 p.m. or 5 p.m. departure times.

Wheelchairs Available for Use

For those requesting use of the company's manual wheelchair, please visit the dockside CFL River Cruise ticket office upon arrival.

Service Animals

We welcome service dogs onboard! The service animal must be harnessed, leashed, or tethered while in public places. Emotional support animals, pets and other animals not covered by ADA guidelines are not permitted. Please visit the ADA's FAQ on service animals for further details.

Boarding Ramps Available

When boarding the ship, guests cross two ramps and enter through a opening (doorway) that is 36" wide. Crew members can assist you in guiding the wheelchair across the gangway. Motorized scooters and electric wheelchairs may not board the ship; guests may utilize our manual wheelchair (based upon availability).

Who gives the tours?

All tours are given by CAC-certified  volunteer docents . Docents receive hundreds of hours of training about Chicago’s architecture and its history. They are storytellers and Chicago experts.

Where do we board the CAC River Cruise?

Meet at the Chicago’s First Lady boat dock at least 30 minutes prior to departure. The dock is located at the southeast corner of Michigan Avenue Bridge and Wacker Drive.

Look for the black awning at the stairway entrance (if using a GPS, enter 112 E. Wacker Drive ).

Are refunds or exchanges available for online ticket purchases?

Refunds and exchanges for ticket purchases are not permitted. Please double-check your dates and times before making a ticket purchase.

Is parking available?

The closest parking garage is located at  111 East Wacker Drive . CAC guests and members receive a discount on parking at this garage for up to 4 hours. You can receive a validated parking sticker at the Center box office or the dockside CFL River Cruise box office. The parking garage is open 24/7.

Several other public parking garages are available in the River North and Loop neighborhoods. You can also book convenient and affordable parking in advance through SpotHero, the nation's leading parking reservations app.

To reserve your parking spot, visit the  Chicago Architecture Center SpotHero Parking Page .

Group & Private Tours

Interested in a tour for a group? Learn more about our group and private tour options.

Fantastic views. Love the history and the facts about architecture! I highly recommend this boat tour to anyone visiting Chicago.

What an amazing tour!!! Our guide was fantastic! He was funny and knowledgeable and made the entire trip very interesting! I would highly recommend for anyone visiting the city; this is definitely one not to miss!

So worth it. This was a highlight of our trip. Just beautiful. Very interesting info, too! We learned a lot and had a great time.

Such a wonderful experience. Megan was very knowledgeable and her love and passion for her city made me fall in love with it too. Highly recommend.

Aerial view of the Chicago Architecture Center River Cruise aboard Chicago’s First Lady. Photo by: Barry Butler

A docent shares stories on a CAC River Cruise. Photo by: Dennis Lee Photography.

The CAC River Cruise is an annual tradition for out-of-town visitors and Chicagoans alike. Photo by: Barry Butler.

Upgrade Your Ticket to See More

Looking for the ultimate Chicago architecture experience? Add admission to the center for just $5 (regular price $14) as an event extra in your Ticketmaster cart.

take the #1 boat tour in north america

As voted by USA Today readers!

Visit the CAC

Exhibitions, on view now.

ReCovered: Lawndale’s Urban Tree Canopy

A FREE pop-up exhibition in Lawndale exploring the role of trees in our city. Opens October 4 and runs through the fall.

Events & Programs

Teen Saturday Studios

January 20 - december 21.

LEGO & Libations

Girls Build!

November 10.

what’s happening at the cac today

Explore everything the Chicago Architecture Center has to offer, from tours to educational programs and exhibitions.

Bring Chicago Home

Skip the packing and ship your souvenir when you shop the CAC Design Store online.

Join Us Next Season for More Sailing Fun Starting Mid-May 2025

Tall Ship Windy

The official flagship of the city of chicago chicago skyline tours & boat excursions sailing on lake michigan from navy pier, the official flagship of the city of chicago chicago skyline sails & tours.

Initial Public Offering Announcement

AMDI plans to conduct its initial public offering (IPO) through the New York Stock Exchange American with the symbol ‘AMDI’ through its underwriter, Kingswood Investments, a division of Kingswood Capital Partners, LLC (or Kingswood), which is acting as the sole representative of the underwriters. AMDI anticipates a public offering price between $3.50 to $4.50.

AMDI is a maritime tour activity and attractions operator with the following wholly-owned operating units: Seas the Day Charters in the U.S. Virgin Islands, Tall Ship Windy in Chicago, Illinois and Paradise Adventures in Panama City Beach, Florida. The Company plans to use the proceeds of its IPO to acquire Paradise Yacht Management and Charter Smarter in the U.S. and British Virgin Islands and the Bahamas.

Interested parties may subscribe to the IPO or obtain a prospectus and more information at  Webull .

You may also obtain the Company’s prospectus and other information at the  SEC website .

Sail in Florida and the Virgin Islands!

Thank you for another fantastic season! We’re already counting down the days until we can set sail with you again aboard Tall Ship Windy in 2024.

If you’re looking for other ways to sail, we invite you to explore our other exciting locations! Tall Ship Windy is proud to be a part of the Amphitrite Digital family of companies.

Join us at Paradise Adventures in Panama City Beach, Florida, where sun-kissed shores await. If you’re dreaming of a week-long yacht vacation, Charter Smarter in the Virgin Islands promises an unforgettable experience. For a full or half day on the water from St. Thomas and St. John in the US Virgin Islands, our team at Seas the Day Charters USVI is ready to make your dreams a reality.

No matter where your compass points, we’re here to create more unforgettable memories with you. Until then, fair winds and following seas.

Paradise Adventures Catamarans and Watersports

Enjoy top-rated boating adventures on the Florida Gulf Coast at Paradise Adventures Catamarans and Watersports!

• Experience inflatable fun on a Privateer Adventure Tour
• Snorkel and explore Shell Island
• Look for dolphins on a Sightseeing Tour or enjoy a Breathtaking Sunset Sail
• Book a private charter on a catamaran, sailboat, powerboat or pontoon boat

Learn more about Paradise Adventures

Charter Smarter

Explore the wonders of the Virgin Islands with an all-inclusive Charter Smarter yacht charter!

• Each week-long adventure includes a professional captain, a skilled chef and all meals and drinks
• Take advantage of all your catamaran’s amenities, water toys and land-based activities in paradise
• Bring your family or friends and create memories that will last a lifetime

Learn more about Charter Smarter

Seas the Day Charters USVI

Enjoy a full or a half-day adventure with Seas the Day Charters USVI!

• Luxury sailing excursions & fast powerboat adventures
• Private & semi-private charters available
• Snorkel with beautiful fish, coral and sea turtles and explore white sandy beaches
• Explore the US Virgin Islands or the British Virgin Islands

Learn more about Seas the Day Charters USVI

Chicago Skyline Sail

Explore Chicago’s scenic shores and enjoy this Windy City boat tour with a relaxing sail around Lake Michigan. Take in the world-famous Chicago skyline, enjoy spectacular city views and discover the Windy City from the water. Select from Pirates and Maritime stories at 1pm, Architectural Tour and Skyline at 3pm and 5pm or a Chicago Sunset Cruise at 7pm.

Hour Glass 75 Minutes | Starting at $39

• Hour Glass 90 Minutes

Fireworks Cruise From Navy Pier 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, 1 Night Only
• Hour Glass One Day Only - VIP Event - 1.5 Hours

4th of July Independence Celebration Sail! Aboard Chicago's Official Tall Ship Windy!

A SPECIAL EVENT SAIL! Treat yourself to an Independence Day Sail from the best seat in town!

Order a cool drink from our bar, then relax and enjoy a leisurely evening listening to patriotic music and enjoying the Chicago skyline. The City of Chicago MAY also have fireworks on July 4th, but officially this has not been announced. Chicago’s Fourth of July celebration is one of the best in the nation. Enjoying this event from Chicago’s official Schooner, Tall Ship Windy, is truly a VIP event. This event sells-out early.

• Hour Glass 2 Hours

Monday Night Blues Summer Concert Series

There is something special about sailing in Chicago combined by kicking off your week and joining us for a 2-hour concert sail. This Navy Pier boat tour sails 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 at sunset from the waters of Lake Michigan, accompanied by the sweet sounds of the blues.

• Frequently Sells Out
• Hour Glass 75 Minutes

Chicago Skyline Sunset Sail

For the best Chicago sunset, visitors and residents alike, join us aboard the 148′ Tall Ship Windy – the official ambassador for the City of Chicago. Departing from Navy Pier daily, you will enjoy a spectacular sailing cruise and enjoy the breathtaking moments as the sun sets gently behind the Chicago Skyline. There is nothing like Chicago at sunset.

• Great for Children!

Educational Sail: Tall Ship Discovery Sail

History comes alive on this exciting Windy City boat tour. Enjoy an educational adventure for curious minds of all ages with the backdrop of the iconic Chicago skyline always in view. Led by our crew-educators, experience a hands-on sailing excursion in Chicago aboard Windy.

• Every night at 5pm!

Happy Arr-our Chicago Architecture and Skyline Sail

Enjoy happy hour drink specials onboard this Navy Pier Boat Tour 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 and an Architectural Tour of Chicago from the water.

Explore Chicago Sailing Special Events

Chicago fireworks cruises, special event sails, welcome aboard tall ship windy.

Tall Ship Windy, sailing from Chicago’s Navy Pier, brings you exciting boat tours that are educational, creative and inspiring. From our daily storytelling adventures and field trips for students to our concert sails to lively Chicago Architectural Tours, there is something for everyone. Enjoy the Chicago skyline as you sail on our tall ship!

For group boat excursions and private sailing charters, email us at [email protected] or call us at (312) 451-2700 .

Tall Ship Windy offers the most spectacular Chicago fireworks cruises during the summer.

Our boat tours are both fun and educational, which makes them the perfect way to see Lake Michigan.

Feel the spirit of centuries past and hoist the sails as part of your Chicago boat excursion on Tall Ship Windy.

There is simply no better way to experience Chicago’s world-famous skyline than on a Windy City Boat Tour with Tall Ship Windy.

Choose Tall Ship Windy For Your Special Event

Tall ship windy chicago sailing reviews.

We went on the "pirate" cruise. They told tales of actual Lake Michigan pirates and made it very entertaining for the kids and the adults. I want to go on this cruise again!

We went on the Lakeside Architecture Tour. It was a very educational and relaxing seventy-five minutes. I highly recommend the experience.

I've set sail on Tall Ship Windy 4-5 times over the past few years, and it is always a good time. You get a nice view of the city and the crew is entertaining and knowledgeable.

If you want humor, entertainment, and an inclusive experience for young and the old, don’t miss this! I appreciate everything about this adventure, and Austin you’re the best!

Had a wonderful sail on a chilly, overcast night! Crew was professional, friendly and informative. Would recommend this trip to anyone, so relaxing. Oh, used a Groupon, an extra bonus!

Best view of the city! Highly recommend the 7pm sail to watch the sunset between the buildings. Fun and knowledgeable crew made the Windy the highlight of our Chicago visit.

The most fun tour we’ve had of Chicago. The crew is fantastic and the tour guide is hilarious. His sense of humor really sets this tour apart from the rest, while still offering interesting insights on the city’s unique skyline. Loved it.

Loved our sail! I love sunsets and this in my opinion was the best way to experience the Chicago skyline. When I return I’d love to do another tour!

Honestly, a perfect experience. Exactly on-time departure and arrival. Perfect boat - size and look. The Captain and crew were friendly and knowledgable. My son raised the sail. Hard. Fun. An experience. The frozen drinks and cold beers were excellent. The views? Wow. A great soundtrack plays during the excursion at perfect volume level. A great time for all ages of Pirates. I guess I liked it :) Just do it. Thank me later.

The Tall Ship Windy is a must thing to do at Navy Pier. Very friendly and funny staff and always a good time, with beautiful views of the city of Chicago.

My husband and I just did the "Pirate and Maritime Stories" tour with Tall Ship Windy and it was fabulous. A lovely cruise around the Navy Pier, while hearing some fascinating pirate history about Chicago. We highly recommend this experience for any age!

I’m a life long Chicagoan and I brought my out of town relatives on this cruise and we all loved it! It was a gorgeous summer late afternoon and the city was just sparkling. I loved having a new view of the city. Crew excellent. My nephew helped hoist a sail. Narrator very entertaining and informative. I thought the price was great for the experience.

What a great experience! Beautiful and ever-changing views of the night skyline from the lake. When they hoisted the sails and turned off the motor, it was so peaceful. The incredible fireworks were the perfect ending to this cruise. Highly suggest!!