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Top Chicago Cruises, Sailing & Water Tours

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42 Chicago Cruises, Sailing & Water Tours

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Did you know?You can reserve your spot today and pay when you're ready.
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Did you know?
You can reserve your spot today and pay when you're ready.Learn more

45-min Chicago River Architecture TourDay Cruises

45-min Chicago River Architecture Tour

star-5
Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.
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  • 45 minutes
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  • Free Cancellation
From  
USD23.00 
From  
USD23.00 
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  • 45 minutes
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  • Free Cancellation

90-min Chicago River Architecture TourDay Cruises

90-min Chicago River Architecture Tour

star-5
Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.
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  • 1 hour 30 minutes
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  • Free Cancellation
From  
USD39.00 
From  
USD39.00 
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  • 1 hour 30 minutes
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  • Free Cancellation

Chicago Architecture Fireworks CruiseNight Cruises

Chicago Architecture Fireworks Cruise

star-4.5
Take advantage of a rare chance to experience Chicago’s illuminated skyline beneath a fantastic fireworks display. This summer evening cruise (available on selected nights), takes you past more than 40 significant works of architecture like the Wrigley Building, Chicago Tribune Tower, John Hancock Center, and more. Your expert guide shares each building’s story, and the cruise concludes with a stunning view of the fireworks from Navy Pier.
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  • 1 hour 30 minutes
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  • Free Cancellation
From  
USD45.40 
From  
USD45.40 
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  • 1 hour 30 minutes
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  • Free Cancellation

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Chicago Architecture River CruiseDay Cruises

Chicago Architecture River Cruise

star-5
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower). Each Architecture River Tour ticket includes a free one-way water taxi pass valid for use any time during the 2020 water taxi season.
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  • 1 hour 15 minutes
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  • Free Cancellation
From  
USD46.87 
From  
USD46.87 
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  • 1 hour 15 minutes
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  • Free Cancellation

Spirit of Chicago Lunch Cruise with BuffetDay Cruises

Spirit of Chicago Lunch Cruise with Buffet

star-4.5
Perfect for families, groups, and corporate outings, the Spirit of Chicago lunch cruise lets you kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.
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  • 2 hours
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  • Free Cancellation
From  
USD74.66 
From  
USD74.66 
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  • 2 hours
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  • Free Cancellation

Chicago Lake and River Architecture TourDay Cruises

Chicago Lake and River Architecture Tour

star-4.5
Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.
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  • 1 hour 30 minutes
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  • Free Cancellation
From  
USD39.00 
From  
USD39.00 
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  • 1 hour 30 minutes
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  • Free Cancellation

Spirit of Chicago Sunset Dinner Cruise with BuffetDining Experiences

Spirit of Chicago Sunset Dinner Cruise with Buffet

star-4.5
Make your evening in Chicago one to remember with this luxury sunset cruise featuring dinner, sightseeing and dancing along the shores of Lake Michigan. Feast your eyes on incredible views of iconic Windy City sights like Navy Pier, the Willis (Sears) Tower, Buckingham Fountain and Soldier Field, then fill your belly with a bountiful all-you-can-eat buffet. Continue the celebration with a live DJ who will mix up a selection of dance favorites.
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  • 3 hours
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  • Free Cancellation
From  
USD112.74 
From  
USD112.74 
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  • 3 hours
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  • Free Cancellation

Chicago Odyssey Dinner CruiseDay Cruises

Chicago Odyssey Dinner Cruise

star-4
Take a gourmet dinner cruise on a high-end luxury yacht with the stunning skyline of Chicago serving as your backdrop. Climb aboard your recently renovated vessel, featuring a sumptuously-appointed rooftop lounge and stylish interior design, for your cruise along Lake Michigan. Then sit down for a 3-course dinner, informed by some of the world’s top celebrity chefs and composed of fresh ingredients cooked right on-board. After dinner, enjoy coffee and tea, captivating views of Chicago landmarks like the Willis (formerly Sears) Tower and Navy Pier, plus musical entertainment provided by the onboard DJ.
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  • 3 hours
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  • Free Cancellation
From  
USD108.66 
From  
USD108.66 
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  • 3 hours
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  • Free Cancellation

Chicago Architectural River CruiseDay Cruises

Chicago Architectural River Cruise

star-4.5
See the towers, piers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.
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  • 1 hour 30 minutes
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  • Free Cancellation
From  
USD49.28 
From  
USD49.28 
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  • 1 hour 30 minutes
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  • Free Cancellation

Chicago Odyssey Fireworks Dinner CruiseDay Cruises

Chicago Odyssey Fireworks Dinner Cruise

star-3
Set sail on Lake Michigan aboard a luxury yacht for a gourmet dinner cruise with views of the Chicago fireworks display. During the 3-hour cruise, the crew serves a 3-course plated meal with dishes prepared by your onboard chef. You can enjoy the stylish interior of the rooftop lounge, dance to DJ entertainment, or relax and soak in the views of the Chicago skyline.
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  • 3 hours
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  • Free Cancellation
From  
USD176.66 
From  
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  • 3 hours
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  • Free Cancellation

Lake Michigan and Chicago River Architecture Cruise by SpeedboatJet Boats & Speed Boats

Lake Michigan and Chicago River Architecture Cruise by Speedboat

star-4.5
Discover Chicago's world-renowned architecture during this sightseeing cruise. Board a comfortable riverboat for a cruise on the Chicago River, viewing landmarks like the Willis Tower and the Tribune Tower while listening to engaging commentary from your guide. Then board a speedboat for an exciting ride up the shore of Lake Michigan for views of Grant Park, the Chicago Harbor, and the Museum Campus.
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  • 1 hour 15 minutes
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  • Free Cancellation
From  
USD49.82 
From  
USD49.82 
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  • 1 hour 15 minutes
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  • Free Cancellation

Lake Michigan Speedboat RideJet Boats & Speed Boats

Lake Michigan Speedboat Ride

star-4.5
Zoom along the shoreline of Lake Michigan, zipping past famous landmarks as you go, during this exhilarating speedboat ride in Chicago. Climb aboard your 2,000-horsepower speed boat at Navy Pier, then hang on for the ride of a lifetime, as you zip past famous attractions like the Willis Tower, Grant Park, and Buckingham Fountain, pausing to learn a little about the history and architecture of the Windy City along the way.
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  • 30 minutes
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  • Free Cancellation
From  
USD32.42 
From  
USD32.42 
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  • 30 minutes
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  • Free Cancellation

VIP: Architectural River Cruise and Chicago Helicopter TourLuxury Tours

VIP: Architectural River Cruise and Chicago Helicopter Tour

star-4.5
Experience Chicago from the air and the water on this two-part tour that features a river cruise and a helicopter ride above the city. First, take a cruise down the Chicago River to learn about the architectural history of the town. Then, board a state-of-the-art helicopter and fly above the skyline. Both tours are fully narrated and pass landmarks including Navy Pier, Wrigley Field, Soldier Field, the John Hancock Center, Willis Tower, and more.
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  • 15 minutes to 1 hour 30 minutes
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  • Free Cancellation
From  
USD195.00 
From  
USD195.00 
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  • 15 minutes to 1 hour 30 minutes
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  • Free Cancellation

Chicago Odyssey Lake Michigan Lunch CruiseDay Cruises

Chicago Odyssey Lake Michigan Lunch Cruise

star-4
Board a luxurious yacht at Navy Pier for a 2-hour lunch cruise along Chicago’s scenic shoreline. Enjoy a three-course gourmet meal as you take in views of the Windy City from a climate-controlled observation deck, then sip coffee or tea while the yacht’s onboard DJ spins a leisurely afternoon playlist.
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  • 2 hours
From  
USD88.26 
From  
USD88.26 
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  • 2 hours

Odyssey Chicago River Architectural Lunch CruiseDay Cruises

Odyssey Chicago River Architectural Lunch Cruise

Travel down the Chicago River on an architecture cruise aboard the "Odyssey." As you pass by some of Chicago's most notable buildings, you'll dine on a 3-course lunch with salad, a main course such as chicken, salmon, pasta, or short ribs, and a dessert such as cheesecake or sorbet. Listen to onboard narration about the city's architecture along the way.
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  • 2 hours
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  • Free Cancellation
From  
USD101.86 
From  
USD101.86 
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  • 2 hours
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  • Free Cancellation

Private Sunset Sail on Lake Michigan with Breathtaking Views of ChicagoDay Cruises

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

star-5
Soak up the views of Lake Michigan and the Chicago skyline with a 2-hour sailing tour. This private charter is completely customizable, giving you the chance to choose your music, route, and up to 5 additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side.
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  • 2 hours
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  • Free Cancellation
From  
USD415.74 
per group
From  
USD415.74 
per group
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  • 2 hours
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  • Free Cancellation

Private Lake Michigan Sailing Charter and Sightseeing Tour of ChicagoDay Cruises

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

star-5
If you’ve ever dreamed of sailing away on your own private sailboat, this is the perfect excursion for you. You and up to five other invited guests will have the exclusive use of a sailboat, complete with captain and crew for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you could even take a turn at the helm.
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  • 2 hours
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  • Free Cancellation
From  
USD466.84 
per group
From  
USD466.84 
per group
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  • 2 hours
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  • Free Cancellation

Chicago Skyline Sightseeing CruiseDay Cruises

Chicago Skyline Sightseeing Cruise

star-5
Escape the bustle of the city on a sailboat tour through Lake Michigan with a convenient departure from Navy Pier. The cruise offers plenty of frame–worthy photo opportunities, including sweeping views of the Chicago skyline rarely seen by visitors. As a popular choice for both locals and visitors, your experience is guaranteed to be family–friendly and tailored to your needs.
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  • 1 hour 15 minutes
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  • Free Cancellation
From  
USD35.84 
From  
USD35.84 
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  • 1 hour 15 minutes
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  • Free Cancellation

Chicago Odyssey Lake Michigan Brunch CruiseDay Cruises

Chicago Odyssey Lake Michigan Brunch Cruise

star-4
Enjoy waterfront views of downtown Chicago on a 2-hour brunch cruise through the heart of the city. Board a luxurious yacht at Navy Pier then relax on deck with a complementary mimosa. Find a comfortable spot on the three climate-controlled observation decks, and enjoy a sumptuous buffet while the onboard DJ spins a leisurely afternoon playlist. Capture unforgettable images of downtown skyscrapers and architectural landmarks as you navigate along the historic shoreline, then loop back and finish your outing at the bustling Navy Pier.
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  • 2 hours
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  • Free Cancellation
From  
USD108.66 
From  
USD108.66 
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  • 2 hours
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  • Free Cancellation

Private Evening Sail in Chicago Ending with the Spectacular Navy Pier FireworksDay Cruises

Private Evening Sail in Chicago Ending with the Spectacular Navy Pier Fireworks

star-5
Treat yourself to an unforgettable Chicago experience with this private sailboat cruise under the Navy Pier fireworks. Over the course of two hours, you’ll sail along Chicago’s beautiful lakefront with a view of the city skyline. You’ll have the perfect vantage point to enjoy the incredible fireworks from Navy Pier. This customizable experience allows you to choose your own, route, music, and guest list.
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  • 2 hours
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  • Free Cancellation
From  
USD530.43 
per group
From  
USD530.43 
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  • 2 hours
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  • Free Cancellation

Lake Michigan Sightseeing CruiseDay Cruises

Lake Michigan Sightseeing Cruise

star-4.5
Take in superlative-worthy views of the beautiful Chicago lakefront and its many landmarks during this 40-minute Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's iconic skyline from a unique perspective. Along the way, you'll listen to informative commentary and take in views of the John Hancock Center and Willis Tower, along with many other landmarks. Plus feel free to bring your own lunch or grab a drink at the onboard bar, during your ride. Please note: This cruise is only 30 minutes during fall and winter
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  • 30 minutes
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  • Free Cancellation
From  
USD27.25 
From  
USD27.25 
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  • 30 minutes
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  • Free Cancellation

Spirit of Chicago Fireworks Dinner Cruise with BuffetDay Cruises

Spirit of Chicago Fireworks Dinner Cruise with Buffet

star-4.5
Celebrate a night out in Chicago with dinner, dancing and sightseeing aboard a three-hour luxury cruise on Lake Michigan. Glimpse top Chicago attractions like Navy Pier, Soldier Field and more while you dine on a lavish, all-you-can-eat buffet! See spectacular views of the Chicago skyline and a live DJ spinning your favorite songs. In the summer months, enjoy a breathtaking fireworks display.
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  • 3 hours
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  • Free Cancellation
From  
USD156.26 
From  
USD156.26 
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  • 3 hours
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  • Free Cancellation

Lake Michigan Sailing Excursion and Sightseeing Tour of the Chicago SkylineDay Cruises

Lake Michigan Sailing Excursion and Sightseeing Tour of the Chicago Skyline

Want to get away from the crowds and see the BEST views of the Chicago? Then you need to come sailing and experience Chicago from the water! Join us for this TWO-HOUR, SEMI-PRIVATE, SHARED SAILING TRIP on Lake Michigan where we’ll sail along the lakefront and take in Chicago’s spectacular skyline. Our SEMI-PRIVATE, SHARED SAILING TRIPS allow a more engaging and personal sailing experience than that of a huge dinner cruise or tour boat filled with strangers. Yes, you may be sailing with a few people that you don’t know. That’s the SHARED part of it. But with a maximum capacity of ONLY 6 passengers, our sailboats provide a more intimate setting. On our sailboats you’re free to engage the captain in casual conversation and even take part in the actual sailing if you so desire. Rest assured, our professional captains will always be there to ensure a safe and enjoyable sailing experience for all. Come Sailing - Chicago’s Premier Sailing Experience and Private Sailing Charter
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  • 2 hours
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  • Free Cancellation
From  
USD117.07 
From  
USD117.07 
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  • 2 hours
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  • Free Cancellation

Odyssey Chicago River Fireworks Dinner CruiseDay Cruises

Odyssey Chicago River Fireworks Dinner Cruise

Book your passage aboard the Odyssey Chicago River ahead of time to guarantee your spot on this popular Chicago River cruise. This modern, glass-enclosed boat makes for a comfortable ride no matter the weather and gives panoramic views of Chicago’s well-known architectural gems on the banks of the river. Dig in to a 3-course plated meal while enjoying live entertainment, including fireworks displays on Wednesdays and Sundays.
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  • 2 hours 30 minutes
From  
USD190.26 
From  
USD190.26 
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  • 2 hours 30 minutes

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
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