Free cancellation: get a full refund up to 24 hours in advance. Learn more
Questions? (888) 680-5729(888) 680-5729

Top Chicago Cruises, Sailing & Water Tours

Category
Select Dates
Filter




Clear Filters
Clear Filters

32 Tours and Activities

Sort by:Default


Chicago Architecture River Cruise

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).
  • Duration: 1 hour
  • Free Cancellation
  • Duration: 1 hour
  • Free Cancellation
From  
US$41.44
From  
US$41.44
See Details

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

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.
  • Duration: 6 hours
  • Free Cancellation
  • Duration: 6 hours
  • Free Cancellation
From  
US$124.00
From  
US$124.00
See Details

NEW TO VIATOR

Chicago River Architecture Tour

Discover the architectural gems of the Windy City from an ideal vantage point on a 75-minute 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.
  • Duration: 1 hour 15 minutes
  • Free Cancellation
  • Duration: 1 hour 15 minutes
  • Free Cancellation
From  
US$39.00
From  
US$39.00
See Details

Chicago Architectural River Cruise

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.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
US$49.28
From  
US$49.28
See Details

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.
  • Duration: 3 hours
  • Duration: 3 hours
From  
US$169.86
From  
US$169.86
See Details

NEW TO VIATOR

Chicago Land and River Architecture Tour: North and South Shores

Whether you’re short on time or want to orient yourself to Chicago, a 3.5-hour land and river tour is the perfect option. The comprehensive itinerary takes you through both the North and South sides. Listen as your guide tells insider stories about the people who shaped the city. After the land tour, rest your feet and see the city from a unique vantage point during a 90-minute river cruise.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
US$89.95
From  
US$89.95
See Details

Chicago Odyssey Fireworks Dinner Cruise

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.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$169.86
From  
US$169.86
See Details

Spirit of Chicago Sunset Dinner Cruise with Buffet

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.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$108.66
From  
US$108.66
See Details

NEW TO VIATOR

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.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
US$48.00
From  
US$48.00
See Details

Chicago Odyssey Dinner Cruise

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.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$156.26
From  
US$156.26
See Details

SPECIAL OFFER

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.
  • Duration: 15 to 90 mins
  • Free Cancellation
  • Duration: 15 to 90 mins
  • Free Cancellation
US$224.99
US$46.99 savings
From  
US$178.00
US$224.99US$46.99 savings
US$224.99
US$46.99 savings
From  
US$178.00
US$224.99US$46.99 savingsSee Details

Chicago Odyssey Brunch Cruise

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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$122.26
From  
US$122.26
See Details

Chicago Urban Adventure River and Lake Cruise

See the the Second City from the water with a 1.5-hour cruise on the Chicago River and the Lake Michigan shoreline. Take in towering skyscrapers and spot the gargoyles that live on to of the city’s historic buildings. Hear stories about the city’s history and culture as you pass Chicago landmarks, museums and iconic buildings. Capture unforgettable images of the city skyline from Lake Michigan, and get a unique look at Chicago that’s perfect for all ages.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
US$36.00
From  
US$36.00
See Details

Chicago City Tour and Chicago River Cruise

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.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
US$73.95
From  
US$73.95
See Details

Spirit of Chicago Lunch Cruise with Buffet

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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$74.66
From  
US$74.66
See Details

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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$389.76
From  
US$389.76
See Details

Rock the Yacht: All White Midnight Yacht Party Aboard the Spirit of Chicago

The July 4th celebrations continue onto the weekend aboard this all-white midnight fiesta on #TheLake. A night of drinks, great music, and unmatched views of Chicago’s skyline at its finest. What more could you ask for? Catch us living it up aboard The Spirit of Chicago for the best 4th of July weekend yacht party in ChiTown! Tickets will move fast, so secure your spot on this epic patriotic party cruise before it’s too late.
  • Duration: 3 hours
  • Duration: 3 hours
From  
US$35.50
From  
US$35.50
See Details

Chicago Architecture Fireworks Cruise

Take advantage of a rare chance to experience Chicago’s illuminated skyline beneath a fantastic fireworks display. This 90-minute cruise, offered on Wednesday and Saturday evenings all summer, 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.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
US$42.56
From  
US$42.56
See Details

Lake Michigan Sightseeing Cruise

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.
  • Duration: 40 minutes
  • Free Cancellation
  • Duration: 40 minutes
  • Free Cancellation
From  
US$25.76
From  
US$25.76
See Details

NEW TO VIATOR

Chicago Fireworks Cruise

Enjoy your favorite drink while gazing Chicago’s magnificent architecture and finish your cruise with fabulous light show, at Navy Pier. Enjoy drink specials on board such as $7 Beer, $9 Wine, $10 Mixed Drinks. You can also purchase the optional Bar Package at the Ticket Office upon arrival for $22.
  • Duration: 2 hours
  • Duration: 2 hours
From  
US$49.28
From  
US$49.28
See Details

Chicago Odyssey Lunch Cruise

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.
  • Duration: 2 hours
  • Duration: 2 hours
From  
US$88.26
From  
US$88.26
See Details

Lake Michigan Sightseeing Fireworks Cruise

If you’re visiting Chicago during summer, this Lake Michigan cruise is a family-friendly activity that all ages can enjoy. Board a spacious vessel and learn about about Chicago’s colorful history and architectural history. Relax with a drink from the onboard cash bar and take in panoramic views of the skyline to one side and expansive blue waters on the other. The ride culminates with an impressive fireworks display over Navy Pier.
  • Duration: 1 hour
  • Free Cancellation
  • Duration: 1 hour
  • Free Cancellation
From  
US$31.36
From  
US$31.36
See Details

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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$389.76
From  
US$389.76
See Details

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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$445.76
From  
US$445.76
See Details


Book online or call
(888) 680-5729
(888) 680-5729