Top Chicago On the Water
Saved to wishlist!
When are you traveling?
Popular
Search experiences that may have limited interaction with crowds.
Search experiences with increased health and safety practices.
These experiences are highly rated by travelers and have met our top quality standards.
Search tours and activities you can do from home.
You are viewing Virtual Experiences in Chicago. See more Virtual Experiences around the globe. 🌎
Martial Arts Classes
Sports Lessons
4WD Tours
Skydiving
Escape the Room
Flight Simulator
Helicopter Tours
4WD Tours
Aquariums
Nature Walks
Bike Rentals
Mountain Bike Tours
Scavenger Hunts
Price
Duration
Time of Day
RatingClear
Specials
17 Chicago On the Water | All Chicago Tours
Sort by:Featured

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago
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
From
$427.28
per group
From
$427.28
per group
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago
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
From
$427.28
per group
From
$427.28
per group
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

Real Pirates of the Inland Seas: Chicago Pirate-Themed Sailboat Tour
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
From
$40.46
From
$40.46

Chicago Odyssey Lake Michigan 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.
…More
From
$88.26
From
$88.26
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

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 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
From
$74.66
From
$74.66
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

Chicago Odyssey Dinner Cruise
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
From
$108.66
From
$108.66
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

Aqua Water Trike Rentals
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
From
$13.50
From
$13.50
Face masks required for travelers in public areas
Temperature checks for travelers upon arrival
Regular temperature checks for staff

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 or grab a drink at the onboard bar, during your ride.
…More
From
$25.07
From
$25.07
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience

Chicago Odyssey Lake Michigan 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.
…More
From
$108.66
From
$108.66
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

Chicago Architecture River Cruise
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
From
$38.85
From
$38.85
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience

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.
…More
From
$169.86
From
$169.86
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

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
From
$250.00
per group
From
$250.00
per group
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers

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.
…More
From
$76.95
From
$76.95
Transportation vehicles regularly sanitized

90-min Chicago River Architecture Tour
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.
…More
From
$39.00
From
$39.00
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

Chicago Lake and River Architecture Tour
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.
…More
From
$39.00
From
$39.00
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

45-min Chicago River Architecture Tour
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.
…More
From
$23.00
From
$23.00
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

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. Tour departures from 465 N. McClurg Ct.
…More
From
$49.28
From
$49.28
Face masks required for guides in public areas
Social distancing enforced throughout experience
Regular temperature checks for staff
- Art & Culture
- Classes & Workshops
- Food & Drink
- Kid-Friendly
- Outdoor Activities
- Active & Outdoor Classes
- Extreme
- Fun & Games
- In the Air
- Motor Sports
- Nature and Wildlife
- On the Ground
- On the Water
- Boat Rentals
- Coffee Cruises
- Lunch Cruises
- Sailing
- Sightseeing Cruises
- Water Equipment Rentals
- Seasonal & Special Occasions
- Tickets & Passes
- Tours, Sightseeing & Cruises
- Travel & Transportation Services
- Unique Experiences
- Wrigley Building
- Chicago Picasso (The Picasso)
- Prairie Avenue Historic District
- LEGOLAND® Discovery Center Chicago
- Water Tower Place
- Second City
- Tommy Gun's Garage
- Chicago Children's Museum
- Museum of Science and Industry
- Rookery Building
- Marquette Building
- Chicago Board of Trade Building
- Art Institute of Chicago
- United Center
- Lookingglass Theatre Company
- Harold Washington Library Center (Chicago Public Library)
- American Writers Museum
- University of Chicago
- Wrigleyville
- Soldier Field
Things to do near Chicago
- Things to do in Illinois
- Things to do in Cleveland
- Things to do in Nashville
- Things to do in Pittsburgh
- Things to do in Toronto
- Things to do in Niagara Falls & Around
- Things to do in Niagara Falls
- Things to do in Buffalo
- Things to do in Branson
- Things to do in Greenville
- Things to do in Atlanta
- Things to do in Washington DC
- Things to do in Baltimore
- Things to do in Ohio
- Things to do in Ontario