Top Chicago On the Water

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

1 to 2 hoursFree Cancellation

(25)

from $40

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.

Explore Chicago's legendary architecture and history.

Chicago River 90-Minute Architecture Tour

(10,351)

from $45

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.

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

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

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.

(3,343)

from $28

See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

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.

4.5

(356)

from $50

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

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).

(16,435)

from $39

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

4.4

(928)

from $33

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.

Chicago Architectural River Cruise

(839)

from $50

Chicago Lake and River Architecture Tour

This tour cruises the Chicago River and Lake Michigan.

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.

(2,355)

from $45

Chicago Architecture Center River Cruise aboard First Lady

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

4.9

(6,328)

from $57

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.

Chicago Sightseeing River and Lake Cruise

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.

(617)

from $46

Lake Michigan 30-Minute Speedboat Ride

30 minutesFree Cancellation

4.1

(348)

from $36

Chicago River 90-Minute Architecture Boat Tour

(1,785)

from $37

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.

Chicago Architecture Tour and Speedboat Ride and Lake Michigan

Chicago Seadog River & Lake Architectural Tour

1 hour 15 minutesFree Cancellation

4.5

(277)

from $48

Lake Michigan Fireworks Cruise in Chicago

2 to 3 hours

4.2

(130)

from $55

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Chicago 3D Fireworks Cruise

4.5

(77)

from $85

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!

4.2

(242)

from $52

Chicago River Ghost & Dark History Night Cruise

Chicago River Ghost & Dark History Night 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.

4.1

(146)

from $46

Historical and Architectural Chicago Fireboat River & Lake Cruise

Historical and Architectural Chicago Fireboat River & Lake Cruise

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.

4.9

(360)

from $47

Small-Group Sightseeing Boat Tour in Chicago

Small-Group Sightseeing Boat Tour in Chicago

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.

5.0

(99)

from $89

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

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

3.9

(365)

from $63

1 hour 15 minutes

City Cruises: Chicago Fireworks Premier Dinner Cruise

(24)

from $91

2 to 3 hoursFree Cancellation

3.2

(73)

from $153

Admire a side of Chicago that few other visitors get to experience—and enjoy a relaxing trip out on the water, tailored to your party—with this private sailboat charter and sailing tour. You and up to five other guests will have the exclusive use of a sailboat, complete with a captain for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you can even take a turn at the helm.

Heading out to Four Mile Crib on a beautiful day of sailing.

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Golden Hour Motorized Paddleboard Tours w/ Mobile DJ

5.0

(70)

from $508

Per group

1 hourFree Cancellation

5.0

(2)

from $105

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

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

alyssa_l, May 2026

Fun daytime activity in Chicago!

A fun activity for a beautiful Chicago day! The guide who greeted us was so friendly and helpful. He gave us great instructions, locked up my bag for when we were on the water, and got us all set up to go. The wind made the water a little choppy but it’s to be expected. The water color was gorgeous. Highly recommend!

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Darcy_S, May 2026

Great food, great guide, great biking

This was an awesome tour. Matt was our guide and it was his first solo tour and he did a great job. Go hungry! This is not “tastes” of food, it is a full on meal by the end of the day. The biking was easy, you are on some city streets, Matt had everything under control and we felt safe the whole time. I would highly recommend this tour.

Chicago's Downtown Donut & Family-Friendly History Walking Tour

Kimberly_K, Apr 2026

Book this tour!

BOOK THIS TOUR!! My sister and I had a couple of hours before we left Chicago and booked this walking donut tour. We had an absolute blast!! Jackson was a great tour guide. The donuts were absolutely delicious and plentiful. You won't go away hungry. The walking tour was insightful and interesting. One of our favorite adventures of the weekend.

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

chloe_b, Dec 2025

Thank you leslie <3

Leslie made our experience wonderful! We celebrated my girlfriend’s birthday by doing the brunch. Even though it was raining, it was still beautiful! Leslie made sure that our mimosas were filled, the staff was very friendly, and food was delicious. We will definitely be back for another brunch or dinner!

Field Museum of Natural History Admission Tickets

Robert_J, Dec 2025

Get the Extras... worth it!

Even though sometimes it is annoying to have to pay extra for some installations, it is worth it here at the Field. The extra admission (I am sure) helps with the installation and creation of the "extras". We saw "After the Dinosaurs" and the detail, stories, timeline and everything made it a wonderful experience for the family. We used to bring the kids here all the time (from Wisconsin) when they were younger, and now that they are teens they are still fascinated by it all!

Chicago Seadog River & Lake Architectural Tour

Steve_S, Sep 2025

Ryan and his entire team...

Ryan and his entire team were fantastic. They provided fun and engaging tour also allowing time for questions. We highly recommend attending this tour. It is suitable for all ages and especially fun for those who are interested in learning about the architecture of the downtown area.

Small-Group Sightseeing Boat Tour in Chicago

Matthew_P, Aug 2025

Perfect ending to a great family trip to Chicgao!

This was an absolute awesome experience! Highly knowlegable and friendly captian! Good mix of excitement and information. Perfect for a family! Way better than one of those crowded commercial river tours...our captain previously worked for one of those and had extensive knowledge! 1000x recommend!