Recent Searches
Clear

Top Chicago On the Water

Saved to wishlist!
Dates
Select Dates
Cruises & Sailing
Cruises & Sailing
Day Cruises
Day Cruises
Water Equipment Rentals
Architecture Tours
Architecture Tours
Water Tours
Water Tours
Arts & Design
Arts & Design
Sunset Cruises
Sunset Cruises
Night Cruises
Night Cruises
City Tours
City Tours
Culinary Tour
Culinary Tour
Sailing
Sailing
Sightseeing Tours
Sightseeing Tours
Dinner Cruises
Dinner Cruises
Half-day Tours
Half-day Tours
Historical Tours
Historical Tours
Power Boats
Power Boats
Boat Rentals
Boat Rentals
Private Sightseeing Tours
Private Sightseeing Tours
Night Tours
Night Tours
Speed Boat Rentals
Speed Boat Rentals
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
$0
$500+
Duration
Time of Day
RatingClear
Specials

49 results | All Chicago Tours

Revenue may affect this sort orderWhy you are seeing these results Sort by: Featured

Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
8513
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
From
$46.87
From
$46.87

90-Minute Chicago River Architecture Tour
Likely to Sell OutLikely to Sell Out

90-Minute Chicago River Architecture Tour

star-4.5
2194
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
  • 1 hour 30 minutes
  • Free Cancellation
From
$42.00
From
$42.00

Chicago Lake and River Architecture Tour
Likely to Sell OutLikely to Sell Out

Chicago Lake and River Architecture Tour

star-4.5
863
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
  • 1 hour 30 minutes
  • Free Cancellation
From
$42.00
From
$42.00

Lake Michigan Sightseeing Cruise

Lake Michigan Sightseeing Cruise

star-4.5
447
Take in iconic views of the beautiful Chicago lakefront and its many landmarks during this Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's 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
From
$28.34
From
$28.34

Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship

Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship

star-4.5
299
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. Select from Pirates and Maritime Stories Sail at 1pm, Skyline/Architectural Theme at 3pm and 5pm, and Skyline Sunset Sail at 7pm. This sail is approximately 75 minutes. The ship leaves promptly at the scheduled time, please allow for time to park, off the pier if necessary.
More
  • 1 hour 15 minutes
  • Free Cancellation
From
$49.00
From
$49.00

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1515
Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.
More
  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
From
$46.00
From
$46.00

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
2898
Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
More
  • 2 hours
  • Free Cancellation
From
$35.00
From
$35.00

Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

star-5
475
Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. Upgrade your tour to include three pours of local craft beer.
More
  • 3 hours
  • Free Cancellation
From
$74.99
From
$74.99

Chicago Small-Group City Tour with Optional Architecture River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Small-Group City Tour with Optional Architecture River Cruise

star-5
520
Explore Chicago's iconic landmarks on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore downtown and Northside neighborhoods. You have a chance to get out and visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.
More
  • 2 to 4 hours
  • Free Cancellation
From
$43.95
From
$43.95

Chicago CityPASS

Chicago CityPASS

star-4.5
366
Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Shedd Aquarium, Skydeck Chicago, and the Field Museum plus your choice of admission to 3 of the following attractions: Adler Planetarium, Art Institute of Chicago, Museum of Science and Industry, Chicago, and the 360 CHICAGO Observation Deck. Also enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers. Attractions may be required to verify proof of full COVID-19 vaccination (14 days past final vaccine dose) before allowing entry. Please review attraction requirements before visiting Chicago.
More
  • 9 days
  • Free Cancellation
From
$114.00
From
$114.00

Field Museum of Natural History Admission Tickets

Field Museum of Natural History Admission Tickets

star-4.5
195
Delve deep into the world of natural history with this Field Museum admission ticket in Chicago. Spend as long as you like exploring the museum's collection of more than 26 million artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Time travel through 13,000 years of history in the Americas, from the Ice Age to Inca and Aztec temples. Take advantage of the free daily tours, led by Field Museum docents.
More
  • 4 hours
  • Free Cancellation
From
$35.00
From
$35.00

Underground Donut Tour: Chicago's First Donut Tour
Likely to Sell OutLikely to Sell Out

Underground Donut Tour: Chicago's First Donut Tour

star-5
468
Sample some of the Windy City’s tastiest donuts on this Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit to some of Chicago’s tastiest donut purveyors, offering a chance to savor all of your favorite varieties, on the city's only donut-themed excursion. All tastings are included, and vegan, gluten-, and nut-free options are also available.
More
  • 2 hours
  • Free Cancellation
From
$40.00
From
$40.00

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

star-5
387
Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following an informative guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Gold Coast, Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and Chicago’s Lakefront trail. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.
More
  • 4 hours
  • Free Cancellation
From
$89.99
From
$89.99

30 Minute Lake Michigan Speedboat Ride

30 Minute Lake Michigan Speedboat Ride

star-4
177
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
From
$39.21
From
$39.21

Chicago Architecture Boat Tour
Likely to Sell OutLikely to Sell Out

Chicago Architecture Boat Tour

star-5
485
Chicago is famous for its architecture, and the best way to see it is on a cruise down the Chicago River. Glide by historic and modern marvels like the Civic Opera House, Wrigley Building, and Willis Tower from the comfort of an open-deck boat. Live narration reveals each building’s fascinating history, so you'll learn more than you would just observing on your own.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$32.00
From
$32.00

Chicago River Tiki Bar Cruise from Chicago Riverwalk

Chicago River Tiki Bar Cruise from Chicago Riverwalk

star-4
55
Chicago is well known for its architecture and many visitors admire the buildings on a cruise along the Chicago River. Take your river cruise to the next level aboard a floating tiki bar that allows you to take in all the sights with a drink in hand. Your captain also enhances the atmosphere with island tunes as you enjoy your leisurely sail.
More
  • 1 hour 15 minutes
  • Free Cancellation
From
$30.00
From
$30.00

Chicago 3D Fireworks Cruise
Likely to Sell OutLikely to Sell Out

Chicago 3D Fireworks Cruise

star-4
109
Enjoy Chicago’s fireworks in 3D during a 2-hour boat cruise on the Chicago River or Lake Michigan. Capture stunning photos of Chicago’s skyline from the Lake on Saturdays or from the mouth of the river on Wednesdays. Before the fireworks begin, learn about the history of The Windy City as your boat cruises along the waterfront, passing sights including Buckingham Fountain, Museum Campus and the John Hancock Building. Hear informative commentary from your onboard guide about the landmarks, the locks system and more, then sit back with the best seats in the city for the spectacular fireworks show.
More
  • 2 hours
From
$45.00
From
$45.00

Chicago Urban Adventure River and Lake Cruise

Chicago Urban Adventure River and Lake Cruise

star-4.5
153
See the the Second City from the water with a sightseeing cruise along 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.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$42.00
From
$42.00

Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

star-5
786
Enjoy a quintessential Chicago experience when you go on an architecture-themed river tour. Pick from multiple convenient start times, and board your vessel—the Lady Liberty—directly from the Chicago Riverwalk. Your trained docent guides will give you a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and you can spy landmarks like the Marina City towers and Navy Pier from the water’s edge.
More
  • 1 hour 30 minutes
From
$56.00
From
$56.00

45-Minute Chicago River Architecture Tour from Magnificent Mile
Likely to Sell OutLikely to Sell Out

45-Minute Chicago River Architecture Tour from Magnificent Mile

star-4.5
233
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
  • 45 minutes
  • Free Cancellation
From
$25.00
From
$25.00

Chicago Lunch Cruise on Lake Michigan
Likely to Sell OutLikely to Sell Out

Chicago Lunch Cruise on Lake Michigan

star-3.5
115
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
From
$81.82
From
$81.82

Chicago Premier Lake Michigan Lunch Cruise

Chicago Premier Lake Michigan Lunch Cruise

star-4
35
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
From
$98.22
From
$98.22

Chicago Premier Dinner Cruise on Lake Michigan
Likely to Sell OutLikely to Sell Out

Chicago Premier Dinner Cruise on Lake Michigan

star-3.5
192
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
  • 2 hours 30 minutes
From
$180.18
From
$180.18

Chicago by Night: 90 Minute River and Lakefront Cruise

Chicago by Night: 90 Minute River and Lakefront Cruise

star-4.5
52
Discover the beauty of Chicago at night during a 1.5-hour cruise on the Chicago River and Lake Michigan. Watch the city sparkle as you pass landmarks such as Museum Campus, Willis Tower, Aon Center and the John Hancock Building, and the illuminated waters of Buckingham Fountain. You'll learn about the history of the city from live commentary by your knowledgeable guide as you glide along the waterfront of Chicago.
More
  • 1 hour 30 minutes
From
$45.00
From
$45.00

Filters

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 On the Water in Chicago are taking additional safety precautions?
Q:
What On the Water in Chicago are good for avoiding crowds?
A:
These hidden gems in Chicago may have limited interaction with crowds: