Chicago On the Water

Explore Chicago's iconic architecture and skyline with on-the-water tours including river cruises and Lake Michigan cruises. Book your Chicago water tour today!

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Chicago Architecture Center River Cruise aboard First Lady

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 Chi

★ 4.9 (7641)

From $57.00 USD

Chicago Architecture River Cruise

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of th

★ 4.8 (17211)

From $39.00 USD

Chicago By Night River and Lake Cruise

Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night! Enjoy breathtaking views of the dramatic skyscrapers and Buck

★ 4.5 (468)

From $50.00 USD

Chicago City Tour with Architecture River Cruise Option

Uncover the Windy City on Chicago’s premier guided minibus tour! Discover 20+ top landmarks with photo stops at Cloud Gate "The Bean", Museum Campus, & the hist

★ 4.8 (747)

From $49.95 USD

Chicago CityPASS®

Experience 5 top attractions and save up to 50% with Chicago CityPASS® tickets. One simple purchase removes the stress of planning, so you can relax and enjoy y

★ 4.4 (542)

From $144.00 USD

Chicago Fireboat Fireworks Cruise

Enjoy an unforgettable evening on Lake Michigan with the Chicago Fireworks Cruise. Witness the stunning skyline as you glide across the water, leading up to the

★ 4.5 (19)

From $63.13 USD

Chicago Full-Day Walking Food Tour with Free Bike or Kayak Rental

Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary flavors

★ 5.0 (3)

From $99.00 USD

Chicago Jet Ski Rentals

Rent a premium Yamaha VX jet ski and ride the waves on Lake Michigan with Rev & Ride Adventures. Offering flexible 1 hour ride times, this is a great opportunit

From $170.00 USD

Chicago Lake and River Architecture Tour

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years of fascinating soc

★ 4.7 (2492)

From $48.00 USD

Chicago Private Rental Yacht Charter

S. Silvera Charters offers a unique luxury yacht rental for those looking to create unforgettable memories on the water. Perfect for special events or leisurely

★ 4.3 (3)

From $1,300.00 USD

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introdu

★ 4.6 (3778)

From $28.00 USD

Chicago River 90 Minute 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 lega

★ 4.7 (11316)

From $45.00 USD

Chicago River 90-Minute Architecture Boat Tour

Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a profession

★ 4.8 (1992)

From $37.00 USD

Chicago River Fireworks Cruise

Enjoy the Navy Pier Fireworks from the Chicago River. A brief version of Wendella's Lake Michigan Fireworks Cruise, this experience is 45 minutes and does not g

★ 3.3 (3)

From $32.00 USD

Chicago River Floating Tiki Bar Cruise Friday and Saturday

Set sail for an unforgettable evening aboard the River Star or Island Time, where the drinks are flowing and the views are unmatched. Enjoy a refreshing beverag

★ 4.8 (27)

From $42.00 USD

Chicago River Tiki Bar Party Cruise from Chicago River Wednesdays

See Chicago the Island Party Way. Our floating Tiki Bar offers you the opportunity to take in all the sights and sounds as you relax and enjoy a beverage. Have

★ 4.0 (129)

From $43.00 USD

Chicago Seadog River & Lake Architectural Tour

Soak in unobstructed views of Chicago’s world-famous architecture from the water with an exciting ride on our Seadog River and Lake Architectural Tour! Sail thr

★ 4.5 (317)

From $42.84 USD

Chicago Shoreline Adventure Boat Tour

This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military Williard Marine, which prov

★ 5.0 (40)

From $90.00 USD

Chicago's Fireworks Show aboard Tall Ship Windy!

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats

★ 4.7 (26)

From $113.73 USD

Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street Beach

Experience the best Chicago kayak rentals and Chicago SUP & paddleboard rentals from our unbeatable location at Ohio Street Beach, just steps from Navy Pier in

★ 4.8 (26)

From $39.99 USD

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

Enjoy a picturesque day dining on Lake Michigan with our Premier Chicago Brunch Cruise. You’ll indulge in a chef-prepared buffet meal featuring savory and sweet

★ 3.9 (33)

From $120.28 USD

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Sail along the magnificent skyline on our Premier Plus Chicago Brunch Cruise. A chef-curated menu of plated brunch specials will delight your palate while unpar

★ 4.5 (89)

From $84.74 USD

City Cruises Chicago: River Architectural Lunch Cruise

Fine dining and unrivaled skyline views await from the moment you step aboard our Premier Plus Chicago Lunch Cruise. A selection of delectable plated lunch spec

★ 4.4 (44)

From $92.94 USD

City Cruises Chicago: Signature Brunch Cruise on Lake Michigan

Set sail for a memorable experience on Lake Michigan with a Signature Chicago Brunch Cruise that is as scenic as it is delicious! You'll savor a chef-prepared b

★ 3.7 (9)

From $99.78 USD

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

Join us for an unforgettable afternoon on Lake Michigan with a Signature Chicago Lunch Cruise. Whether it’s a family outing or a meal with friends, upgrade your

★ 4.0 (388)

From $62.87 USD

Golden Hour Motorized Paddleboard Tours w/ Mobile DJ

One of a kind experience you can only find in Chicago. Motorized paddle boards take the stress out of paddling. LED-lights make the boards illuminate the water

★ 5.0 (2)

From $105.00 USD

Historical and Architectural Chicago Fireboat River & Lake Cruise

Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel on Lake Michigan and through the Chicago River seeing the sights.

★ 4.9 (514)

From $38.76 USD

Lake Michigan 30 Minute Speedboat Ride

Enjoy Chicago’s iconic skyline with an exciting speedboat Tour on Lake Michigan. Departing from Navy Pier, the Lakefront Speedboat Tour is the best way to view

★ 4.1 (360)

From $45.16 USD

Lake Michigan Fireworks Cruise in Chicago

No city embraces summer quite like Chicago. Join in the celebration with friends and family on this epic fireworks cruise. Get up-close and personal every Wedne

★ 4.2 (142)

From $60.00 USD

Lake Michigan Skyline Cruise in Chicago

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions. Cruise along Lake Michigan and enjoy st

★ 4.4 (956)

From $30.00 USD

Private Chicago City Minibus Tour

Don’t miss Chicago’s famous sights and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on

★ 5.0 (1)

From $999.00 USD

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed capt

★ 5.0 (73)

From $507.96 USD

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lak

★ 4.7 (32)

From $91.23 USD

Unforgettable Small Group Biking Tours from Chicago to Milwaukee

Our tours have varying difficulty levels to accommodate different skill levels. We take every safety precaution available to prioritize your well-being. Our rou

From $349.00 USD