Top Chicago Cruises, Sailing & Water Tours

Chicago Architecture River Cruise

• 2,473 Reviews
• Cruise down the Chicago River to see the city's famous architecture on this 60-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 City Minibus Tour with Optional Architecture River Cruise

• 103 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. The city tour ends at Millennium Park, home of the famous Cloud Gate sculpture, commonly referred to as "the bean."  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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Odyssey Chicago River Dinner Cruise

• Cruise down the Chicago River in style during this 3-hour dinner cruise aboard the Odyssey. Watch the beautiful city and its architecture pass by through the ship’s panoramic windows. Then sit down to delicious 3-course meal accompanied by DJ entertainment to set the mood for your journey. A full-service bar complete with microbrews, creative cocktails, and a wine list is also available for purchase.
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Odyssey Chicago River Lunch Cruise

• Enjoy beautiful views of Chicago’s architectural marvels on this lunchtime river cruise. Board the glass-enclosed Odyssey Chicago River and admire local landmarks like Tribune Tower, the Wrigley Building, and Willis Tower while feasting on a gourmet meal that may feature everything from jumbo crab cakes and baked salmon to maple and mustard glazed chicken breast and braised beef short ribs.
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Chicago Architectural River Cruise

• 141 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 River Architecture Tour

• Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire. This comprehensive tour will navigate through the heart of the city on all three branches of the Chicago River while your professionally-trained architectural guide tells the story of more than 130 years of innovation in design, style and technique and why it is important today.
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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

• 47 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 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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Viator VIP: Willis Tower Skydeck Early Access, Trolley City Tour and Chicago River Cruise

• 102 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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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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Spirit of Chicago Sunset Dinner Cruise with Buffet

• 86 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

• 86 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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Chicago Odyssey Valentine's Day Dinner Cruise

• Enjoy a romantic dinner and beautiful views on this Valentine’s Day river cruise through downtown Chicago. Board the newly renovated, glass-enclosed Odyssey Chicago River and admire the glittering lights of local landmarks like Tribune Tower, the Wrigley Building, and Willis Tower while feasting on a gourmet three-course meal with your special someone.
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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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Valentine's Day Buffet Dinner Cruise

• Book a Valentine's Day dinner cruise aboard the Spirit of Chicago, which gives you epic views of the Chicago skyline lit up for the night. With your special someone by your side, you'll step on to the ship and enjoy a buffet dinner and live DJ entertainment. You can skip the hassle of scrambling for dinner reservations and know you have it all sorted out in advance. Sights include Soldier Field, Buckingham Fountain, the Willis Tower, Navy Pier, and others.
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Chicago Odyssey Fireworks Dinner Cruise

• Expect the exceptional on this 3-hour premier Chicago dinner cruise experience. Newly renovated, this luxury vessel features a newly furnished rooftop lounge, posh atmosphere and stylish interior. Enjoy a 3-course plated meal with celebrity-chef inspired dishes prepared from fresh ingredients right on board. Dance the night away to DJ entertainment or simply relax in the elegant ambiance and take in the unmatched views of the world-famous Chicago skyline as you sail along the shores of Lake Michigan. Take it all in with a front row seat for a breathtaking fireworks show over the Chicago skyline, weather permitting.
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Spirit of Chicago Fireworks Dinner Cruise with Buffet

• 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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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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Odyssey Chicago River Fireworks 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! Your Chicago Dinner Cruise experience will include a spectacular fireworks display on Wednesdays and Saturdays. You will observe the show from the decks of the ship and see the magnificent sky lit up at night.
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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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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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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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