Recent Searches
Clear

Top Chicago On the Water

We’re committed to helping you feel confident as you get back out there. Check out our flexible cancellation policies and learn what steps operators are taking to keep you safe. As conditions evolve, check local regulations for the latest information.

Read More
When are you traveling?
Select Dates
Popular
Search experiences that may have limited interaction with crowds.
Search experiences with increased health and safety practices.
Search tours and activities you can do from home.

You are viewing Virtual Experiences in Chicago. See more Virtual Experiences around the globe. 🌎

Price
US$0
US$500+
Duration
Time of Day
RatingClear
Specials

We’re committed to helping you feel confident as you get back out there. Check out our flexible cancellation policies and learn what steps operators are taking to keep you safe. As conditions evolve, check local regulations for the latest information.

Read More
Select Dates
Today
Tomorrow

28 Chicago On the Water | All Chicago Tours

Sort by:Featured

30 Minute Lake Michigan Speedboat RideJet Boating

30 Minute 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.
More
  • 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$33.58
From
US$33.58
Taking safety measures

Private Pontoon Boat Rental with Pizza IncludedBoat Rentals

Private Pontoon Boat Rental with Pizza Included

star-4.5
Set your own course on this private self-guided cruise along the Chicago River. You're the captain for your group of just eight people, steering the boat wherever you like and getting epic views of the towering buildings along the river. When the munchies hit, grill up the provided pizza on the boat's barbecue and dig in.
More
  • 2 hours
  • Free Cancellation
From
US$297.60
per group
From
US$297.60
per group

Chicago River Kayak TourKayaking

Chicago River Kayak Tour

star-4.5
Set your paddle into the Chicago River on a leisurely 2.5-hour kayak tour past the skyscrapers of downtown Chicago. Both novice and experienced kayakers will be at ease on this excursion past sights such as the Civic Opera Building and the Marina City Towers. Hear fascinating tales of the Windy City as you gaze at a stunning architectural landscape from the water, just how the original Chicago natives originally navigated the area!
More
  • 2 hours 30 minutes
  • Free Cancellation
From
US$66.67
From
US$66.67

Aqua Water Trike RentalsBoat Rentals

Aqua Water Trike Rentals

star-1
Cruise around Lake Michigan and enjoy spectacular views of Chicago on an Aqua Water Trike. This 30-minute rental lets you explore at your own pace and experience the city from the water. There is space for two people per bike and no experience is required—simple hop aboard and pedal your way around the lake.
More
  • 30 minutes
From
US$13.50
From
US$13.50

Chicago River Ghosts and Gangsters Kayak TourKayaking

Chicago River Ghosts and Gangsters Kayak Tour

star-5
Paddle through Chicago’s wild past on a 2.5-hour small group kayak tour on a river that curls through the heart of the Windy City. Learn to navigate your boat and try out paddling techniques, then get ready to navigate the illuminated downtown section of the river. Hear stories of gangsters and their ghosts as you explore the city’s underbelly alongside your guide, and get a glimpse of the city’s gritty past as you travel along riverbanks lined with iconic skyscrapers and historic sites.
More
  • 2 hours 30 minutes
  • Free Cancellation
From
US$66.67
From
US$66.67

Navy Pier Fireworks Chicago Kayak TourKayaking

Navy Pier Fireworks Chicago Kayak Tour

star-5
Kayak down the Chicago River during Wednesday and Saturday nights in the summer to watch the Navy Pier fireworks display. At twilight, follow your adventure guides for this 2.5-hour tour in a double or single kayak. Watch the Windy City's skyline explode with twinkling lights and their dazzling reflections from the water.
More
  • 2 hours 30 minutes
  • Free Cancellation
From
US$70.84
From
US$70.84

Chicago River Architecture Guided Tour by BoatDay Cruises

Chicago River Architecture Guided Tour by Boat

Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a professional guide which leads passengers down the Chicago River to discover the city’s most renowned landmarks. In addition to historical insight on well known structures such as the Civic Opera House, Trump Tower & the Merchandise Mart, passengers will also get a chance to learn about current and upcoming developments. The Chicago River Cruise navigates the three primary branches of the river including the main branch to Navy Pier, the north branch to Goose Island and the south branch to Chinatown.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
US$35.00
From
US$35.00

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.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$49.28
From
US$49.28
Taking safety measures

Chicago Lakeside Architecture TourSailing

Chicago Lakeside Architecture Tour

star-4.5
Get views of Chicago's famous architecture from the deck of a boat during this 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. 
More
  • 1 hour 15 minutes
From
US$40.46
From
US$40.46

Real Pirates of the Inland Seas SailSailing

Real Pirates of the Inland Seas Sail

star-4.5
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.
More
  • 1 hour 15 minutes
  • Free Cancellation
From
US$40.46
From
US$40.46

Chicago Skyline Sailboat CruiseDay Cruises

Chicago Skyline Sailboat Cruise

star-4.5
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.
More
  • 1 hour 15 minutes
  • Free Cancellation
  • Taking safety measures
From
US$35.84
From
US$35.84
Taking safety measures

Chicago Architecture Center River Cruise aboard Chicago's First LadyDay Cruises

Chicago Architecture Center River Cruise aboard Chicago's First Lady

star-5
The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.
More
  • 1 hour 30 minutes
  • Taking safety measures
From
US$53.25
From
US$53.25
Taking safety measures

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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
US$427.28
per group
From
US$427.28
per group
Taking safety measures

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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
US$427.28
per group
From
US$427.28
per group
Taking safety measures

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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
US$108.66
From
US$108.66
Taking safety measures

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.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$108.66
From
US$108.66
Taking safety measures

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.
More
  • 2 hours
  • Taking safety measures
From
US$88.26
From
US$88.26
Taking safety measures

Spirit of Chicago Sunset Dinner Cruise with BuffetHalf-day Tours

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.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$112.74
From
US$112.74
Taking safety measures

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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
US$101.86
From
US$101.86
Taking safety measures

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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
US$74.66
From
US$74.66
Taking safety measures

Odyssey Chicago River Dinner CruiseDay Cruises

Odyssey Chicago River Dinner Cruise

star-5
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.
More
  • 3 hours
  • Taking safety measures
From
US$169.86
From
US$169.86
Taking safety measures

Private Chicago City Mini Bus TourDay Cruises

Private Chicago City Mini Bus Tour

Don’t miss Chicago’s famous sights (now including Wrigley Field!) and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like early skyscraper "The Rookery" (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view in town), Millennium Park (The Bean), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational commentary about the area and its beautiful attractions. Your private tour ensures a more personal experience. If you would like to take the tour at a time other than what is offered, please note in special requests field when booking. The best way to tour at this time! Sanitized vehicles with just your group.
More
  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$200.00
per group
From
US$200.00
per group
Taking safety measures

Chicago Architecture River CruiseDay Cruises

SPECIAL OFFER

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).
More
  • 1 hour 15 minutes
  • Free Cancellation
  • Taking safety measures
From
US$35.49
US$40.33
US$4.84 savings
From
US$35.49
US$40.33
US$4.84 savings
Taking safety measures

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.
More
  • 40 minutes
  • Free Cancellation
  • Taking safety measures
From
US$25.07
From
US$25.07
Taking safety measures

Experiences Themes

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best On the Water in Chicago?
Q:
What On the Water in Chicago are 1 hour or less?
Q:
What tours in Chicago are taking additional safety precautions?
Q:
What tours in Chicago are good for avoiding crowds?

icon_solid_phone
Book online or call
(888) 651-9785
(888) 651-9785