Top Chicago Cruises, Sailing & Water Tours

Chicago Architecture River Cruise

• 2,460 reviews
• Cruise down the Chicago River to see the city's famous architecture on this 75-minute tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like the Aon Center, 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).
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Chicago Architectural River Cruise

• 138 reviews
• See the towers, piers and iconic landmarks along the Chicago River on a 90-minute architectural tour 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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Chicago City Minibus Tour with Optional Architecture River Cruise

• 95 reviews
• Explore Chicago's iconic landmarks on this 2-hour sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus with a small group of twelve people or less. This ensures an intimate touring experience as you enjoy downtown and some North side neighborhoods. You will have a chance to get out and visit several locations such as the 1888 skyscraper called The Rookery, with its Frank Lloyd Wright designed lobby and the unparalleled skyline views from Museum Campus. Listen as your guide talks about the historical and cultural factors that make Chicago unique. Opt to upgrade your tour with a popular 75-minute open-top boat tour on the Chicago River that focuses on the city's renowned architecture. Pick-ups from most downtown Chicago hotels are included.
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NEW TO VIATOR

Viator VIP: Architectural River Cruise and Chicago Helicopter Tour

• 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 you will see Navy Pier, Wrigley Field, Soldier Field, the John Hancock Center, Willis Tower, and more.
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Chicago Odyssey Dinner Cruise

• 43 reviews
• Take a 2.5-3 hour gourmet dinner cruise on a high-end luxury yacht with the stunning skyline of Chicago 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 John Hancock building, plus musical entertainment provided by the on-board DJ.
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Chicago Odyssey Lunch Cruise

• 19 reviews
• 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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Spirit of Chicago Sunset Dinner Cruise with Buffet

• 82 reviews
• Make your evening in Chicago one to remember with this 3-hour 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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Lake Michigan Sightseeing Cruise

• 84 reviews
• 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, along or grab a drink at the on-board bar, during your ride.
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Viator VIP: Willis Tower Skydeck Early Access, Trolley City Tour and Chicago River Cruise

• 100 reviews
• See Chicago from several angles, including the 103rd floor of Willis (Sears) Tower, where you have early access to the Skydeck. This Viator VIP package — available nowhere else — provides a crowd-free morning overlooking city landmarks from glass-enclosed balconies. Follow up your vista with a 2-hour narrated trolley tour past Grant Park, the John Hancock Center, the Wrigley Building and more. Finish with an afternoon cruise on the Chicago River and enjoy a complimentary drink as you discover the city's distinctive skyscrapers from an architecture-savvy guide.
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Odyssey Chicago River Dinner Cruise

• Discover fine dining, upscale entertainment and unparalleled riverfront views aboard the brand new Odyssey Chicago River! The Odyssey Chicago River is a brand new, glass enclosed boat, exclusively on the Chicago River – being the first of its kind!  This beautiful glass ship provides panoramic views of the Chicago River and its famous architecture right from your table all year round!  Included is 3-course plated meal, entertainment, outdoor lounge, high-end table side service, and 3-hour cruise with the best views of the Chicago River!
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Chicago Lakeside Architecture Tour

• 8 reviews
• Get views of Chicago's famous architecture from the deck of a boat during this 75-minute sailing excursion. Learn about the people, plans, and persistence that shaped Chicago's architecture along the shoreline. Hear about the city's historical maritime roots to modern science and technology through your guide's commentary while taking advantage of great photo ops. Choose between an afternoon or early evening departure and relax as you enjoy the sights. 
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Chicago City Tour and Chicago River Cruise

• 88 reviews
• See Chicago from a new perspective during this 4-hour combined bus and boat excursion covering some of the city's most iconic sights. First discover Windy City landmarks such as the skyscrapers of the Loop, Grant Park, Shedd Aquarium, Soldier Field and the former stomping grounds of President Obama during a narrated coach tour. Then take a Chicago cruise aboard your state-of-the-art yacht, enjoying a cruise of the Chicago River that provides a unique look at the city's architecture from the water. This half-day Chicago exploration also includes hotel pickup.
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Real Pirates of the Inland Seas Sail

• 1 review
• Experience Lake Michigan from a perspective rare to visitors and locals alike on a pirate–themed sailboat tour. Your guides tell true but little–known stories about pirates, battles, and treasure hunts as you cruise past sweeping views of the Chicago skyline. Relax on deck while or join your guides for an interactive experience—the flexibility of the tour makes this a popular choice for families with children.
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Chicago Odyssey Brunch Cruise

• 8 reviews
• 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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Private Day Sailing Excursion on Lake Michigan

• 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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Private Chicago Sunset Sail on Lake Michigan

• 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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Spirit of Chicago Lunch Cruise with Buffet

• 1 review
• 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 two-hour cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a deejay, games, and a dance floor to keep your group entertained.
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Chicago Skyline Sightseeing Cruise

• 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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Private Navy Pier Fireworks Sail in Chicago

• 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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Chicago New Year's Eve Luxury Dinner Cruise

• Board a luxury yacht for a 3-hour dinner cruise on New Year's Eve in Chicago. Choose to be seated in the rooftop lounge or explore the well-appointed ship before sitting down for a 3-course, gourmet meal. Relax with tea and coffee while taking in views of the skyline or dancing to the onboard DJ.
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Chicago New Year's Eve Dinner Cruise with Buffet

• Celebrate New Year’s Eve in Chicago with a 3-hour dinner cruise on Lake Michigan, an evening of dining, dancing, and spectacular views. You’ll set sail from Navy Pier aboard a luxurious cruiser, enjoy a freshly-prepared buffet dinner and dessert bar, then get the party started with a top Chicago DJ. This 3-hour New Year’s Eve cruise includes dinner, entertainment, and a Champagne toast at midnight, with the option to upgrade for a private table and open-bar access.
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Private Morning Sail on Lake Michigan

• You will be treated to a morning of relaxation and fun on Lake Michigan on this sailboat charter. You are in charge of the itinerary, guest list, even music choices! There is a fridge and ice aboard if you would like to bring refreshments (no glass please) and if you are feeling adventurous, you can take a turn at the helm.
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Odyssey Chicago River Lunch Cruise

• Discover fine dining, upscale entertainment and unparalleled riverfront views aboard the brand new Odyssey Chicago River! The Odyssey Chicago River is a brand new, glass enclosed boat, exclusively on the Chicago River – being the first of its kind!  This beautiful glass ship provides panoramic views of the Chicago River and its famous architecture right from your table all year round!  Included is 3-course plated meal, entertainment, outdoor lounge, high-end table side service, and 2-hour cruise with the best views of the Chicago River!
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Chicago River Boat Architecture Tour

• 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.
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