Top Chicago On the Water

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Join us in the daytime or evening for City lights and breathtaking views

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.

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Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

4.7

(3,559)

from $28

Likely to Sell Out

Explore Chicago's legendary architecture and history.

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

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Chicago River 90-Minute Architecture Tour

1 hour 30 minutesFree Cancellation

4.7

(10,863)

from $45

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

Escape the bustle of the city during this one or two-hour kayak rental along Lake Michigan in downtown Chicago. Experience the serene waters of the iconic lake as you paddle at your own pace in a single or tandem kayak, enjoying views of Chicago’s famous skyline. Take breaks along nearby urban beachfronts, with the option to extend your rental time. Stand-up paddleboards are also available for rental.

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

1 to 2 hoursFree Cancellation

4.8

(26)

from $40

See Chicago's magnificent skyline at night!

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.

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Chicago By Night River and Lake Cruise

1 hour 30 minutesFree Cancellation

4.5

(427)

from $50

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

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Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,920)

from $39

Skyline Queen showcasing the Chicago Skyline!

See the Second City from the water with a sightseeing cruise along the Chicago River and the Lake Michigan shoreline, offering a unique perspective of towering skyscrapers and historic architecture. This tour offers stories about the city’s history and culture as you pass by Chicago's landmarks, museums, and buildings. Capture unforgettable images of the city skyline from Lake Michigan, ensuring a unique look at Chicago, perfect for all ages.

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Chicago Sightseeing River and Lake Cruise

1 hour 30 minutesFree Cancellation

4.7

(714)

from $46

Chicago Architecture Center River Cruise aboard First Lady

Enjoy a quintessential Chicago experience—and see more of the city's highlights in less time—on an architecture-themed boat tour of the Chicago River. Pick from multiple convenient start times, and board your vessel directly from the Chicago Riverwalk. Thanks to your trained docent guide, receive a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and spy landmarks like the Marina City towers and Navy Pier from the water’s edge.

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Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

4.9

(6,963)

from $57

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.

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Lake Michigan 30 Minute Speedboat Ride

30 minutesFree Cancellation

4.1

(359)

from $37

Take in views of the Chicago skyline and its landmarks during this Lake Michigan sightseeing boat cruise. Enjoy a laidback ride, soaking up panoramic views from this unique perspective. Listen to audio commentary to give you fresh insight into the landmarks you see, like Navy Pier and the Willis Tower, and feel free to bring your own lunch or grab a drink at the onboard bar (own expense).

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Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

4.4

(945)

from $34

Chicago River Ghost & Dark History Night Cruise

See Chicago from a different perspective on this evening cruise that explores the city’s darker side. As twilight settles over the skyline, glide along the Chicago River while hearing chilling tales of disasters, infamous criminals, and eerie legends tied to the city’s past. This relaxed river cruise blends atmospheric storytelling with some of the best nighttime views of Chicago’s renowned skyline and landmarks. Grab a drink from the onboard bar, settle in, and let the city’s shadowy history unfold as you cruise through the heart of downtown. By the end of the journey, you’ll have experienced Chicago’s skyline in a whole new way—while uncovering the chilling events, legends, and mysteries that shaped the city. Please arrive 30 minutes in advance!

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Chicago River Ghost & Dark History Night Cruise

1 hour 30 minutesFree Cancellation

4.1

(200)

from $46

Historical and Architectural Chicago Fireboat River & Lake Cruise

Maximize your Chicago sightseeing on a river cruise—and travel aboard a unique historical vessel, which other tours don’t offer—on this one-of-a-kind excursion. Pick from different departure times and board a classic Chicago fireboat, which served the city’s fire department from 1937 to 1981. As you sail Lake Michigan and the Chicago River, view architectural highlights including the Wrigley Building and Chicago Lighthouse, and chart the boat’s firefighting history via the on-board displays and commentary.

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Historical and Architectural Chicago Fireboat River & Lake Cruise

2 hoursFree Cancellation

4.9

(471)

from $47

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.

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Chicago Architectural River Cruise

1 hour 30 minutesFree Cancellation

4.7

(856)

from $50

Likely to Sell Out

Chicago River 90-Minute Architecture Boat Tour

1 hour 30 minutesFree Cancellation

4.8

(1,875)

from $37

Likely to Sell Out

Lake Michigan Fireworks Cruise in Chicago

2 to 3 hours

4.2

(140)

from $55

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 opportunity to explore the stunning Chicago lakefront. Enjoy a hassle-free experience with online bookings, safety briefings, and included life jackets. Perfect for locals and tourists looking for fun on the water, our jet skis are well-maintained to ensure a safe and enjoyable ride. - Conveniently located at 63rd Street Beach in Jackson Park - Hassle-free online booking with premium safety gear included - Ideal for both first-time riders and experienced adventurers

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Chicago Jet Ski Rentals

1 hourFree Cancellation

from $170

Per group

Chicago Architecture Tour and Speedboat Ride and Lake Michigan

Discover Chicago's world-renowned architecture during this sightseeing cruise. Board a comfortable riverboat for a trip down the Chicago River, viewing landmarks like the Willis Tower and the Tribune Tower while listening to in-depth commentary from your guide. Then board a speedboat for an exciting ride up the shore of Lake Michigan for views of Grant Park, the Museum Campus, and other top sights.

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Chicago Seadog River & Lake Architectural Tour

1 hour 15 minutesFree Cancellation

4.5

(290)

from $42

Likely to Sell Out

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

2 hoursFree Cancellation

4.5

(81)

from $85

Golden Hour Motorized Paddleboard Tours w/ Mobile DJ

1 hourFree Cancellation

5.0

(2)

from $105

Chicago River Floating Tiki Bar Cruise Friday and Saturday

1 hour 15 minutes

4.8

(20)

from $42

Likely to Sell Out

This tour cruises the Chicago River and Lake Michigan.

Chicago Lake and River Architecture Tour

1 hour 30 minutesFree Cancellation

4.7

(2,428)

from $45

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

Kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks on this scenic lunch cruise along Lake Michigan. 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.

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City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

2 hoursFree Cancellation

4.0

(384)

from $63

Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

Set sail on our flagship vessel, where style meets comfort in a Tiki Chic atmosphere. Your adventure begins on the iconic Chicago Riverwalk, where you’ll board a beautifully appointed boat featuring two climate-controlled decks, two full bars, two bathrooms, and both indoor and outdoor viewing areas—perfect for soaking in the sights no matter the weather. As you sip a refreshing beverage, enjoy the rare experience of transiting the historic Chicago Locks—a must-see for locals and visitors alike. Once you glide into the open waters of Lake Michigan, you’ll be treated to breathtaking views of Chicago’s world-famous skyline, framed by the gentle breeze and city lights. Looking to elevate your cruise? Upgrade to the exclusive Admiral’s Lounge, where you’ll enjoy top-shelf spirits, including selections from the Captain’s Private Reserve, all in a more intimate, upscale setting. This is more than just a boat ride—it’s a uniquely Chicago experience you won’t forget!

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Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

1 hour 30 minutes

3.9

(35)

from $42

Small-Group Sightseeing Boat Tour in Chicago

Get a chance to experience the Windy City from multiple vantage points during this two-hour, small-group boat tour in Chicago. Hop aboard a secure and reliable US Navy-built Rigid Inflatable Boat (RIB) for a unique sightseeing experience. Pass by iconic sights such as Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and more, all while comfortably seated in a group capped at only six people.

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Small-Group Sightseeing Boat Tour in Chicago

2 hoursFree Cancellation

5.0

(113)

from $89

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

1 hour 15 minutes

4.8

(28)

from $91

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Top Chicago On the Water

48 results

Top Attractions in Chicago

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago Theatre

Art Institute of Chicago

Chicago River

Chicago Riverwalk

The Magnificent Mile

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago Theatre

Art Institute of Chicago

Chicago River

Chicago Riverwalk

The Magnificent Mile

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago Theatre

Art Institute of Chicago

Chicago River

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