Top Chicago On the Water

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

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.

(3,225)

from USD 28

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,151)

from USD 39

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).

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

4.4

(911)

from USD 33

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

4.5

(73)

from USD 105

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.

Chicago River 90-Minute Architecture Tour

Chicago River 90-Minute Architecture Tour

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.

(10,059)

from USD 45

See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

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.

4.5

(325)

from USD 50

Chicago Architectural River 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!

(826)

from USD 50

Chicago River Ghost & Dark History Night Cruise

Chicago River Ghost & Dark History Night Cruise

4.1

(121)

from USD 46

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.

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

City Cruises Chicago: Signature Lunch Cruise on 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.

3.9

(357)

from USD 63

Chicago Architecture Center River Cruise aboard First Lady

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

4.9

(5,991)

from USD 57

Chicago Lake and River Architecture Tour

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.

(2,339)

from USD 45

Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

(579)

from USD 46

Chicago River 90-Minute Architecture Boat Tour

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.

4.8

(1,659)

from USD 37

Lake Michigan 30-Minute Speedboat Ride

30 minutesFree Cancellation

4.1

(340)

from USD 36

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.

Historical and Architectural Chicago Fireboat River & Lake Cruise

Historical and Architectural Chicago Fireboat River & Lake Cruise

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.

4.9

(298)

from USD 47

Chicago Architecture Tour and Speedboat Ride and Lake Michigan

Chicago Seadog River & Lake Architectural Tour

1 hour 15 minutesFree Cancellation

4.5

(270)

from USD 56

Delve into the world of natural history with admission to Chicago’s Field Museum. Choose general admission or upgrade to visit one or more special exhibits. Spend as long as you like exploring the museum's extensive collection of artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Also take advantage of daily tours led by knowledgeable Field Museum docents, free with admission.

Field Museum of Natural History Admission Tickets

4 hoursFree Cancellation

4.6

(523)

from USD 29

Golden Hour Motorized Paddleboard Tours w/ Mobile DJ

1 hourFree Cancellation

2.0

from USD 105

See Chicago’s legendary Air & Water Show from the best seat in the city! Secure a VIP spot on a Lake Michigan cruise (or Skydeck viewing party) and watch the U.S. Air Force Thunderbirds, Golden Knights, and dazzling stunt pilots soar overhead. Enjoy premium amenities, from fast-track boarding to reserved seating, up-close views, and included food or drinks (per package). With unmatched photo ops and the sound of jets flying overhead, this is a must-see experience for locals and visitors alike—just in time for summer’s biggest Chicago festival. Book early; these shows always sell out fast.

Chicago Air and Water Show VIP Cruise or Skydeck Experience

Chicago Air and Water Show VIP Cruise or Skydeck Experience

2 hours 30 minutes

5.0

(2)

from USD 154

Skip navigating around the city with a map and guidebook and explore Chicago's iconic landmarks in just a few hours on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods, stopping to 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.

Chicago City Tour with Architecture River Cruise Option

Chicago City Tour with Architecture River Cruise Option

2 to 4 hoursFree Cancellation

4.8

(720)

from USD 50

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.

Small-Group Sightseeing Boat Tour in Chicago

Small-Group Sightseeing Boat Tour in Chicago

5.0

(95)

from USD 89

Enjoy a fun and scenic 90-minute Cycleboat Cruise along the beautiful Chicago River! Take in stunning skyline views as you pedal, relax, and sip your favorite drinks with friends, family, or that special someone. • 1.5-hour cruise up and down the iconic Chicago River • Comfortable boat with 10 cycle stations and bench seating at the front • Maximum capacity of 16 passengers — perfect for smaller groups or couples • BYOB! Bring your own beverages and snacks to enjoy onboard • Departs from the Water Plaza on the Chicago Riverwalk (between Wells Street and LaSalle Street bridges) Whether you want a lively group outing or a relaxing ride through the city, this Cycleboat Cruise is one of the most unique ways to see Chicago from the water — no full-boat rental required!

Chicago River Cycleboat Cruise

5.0

(8)

from USD 65

Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

4.6

(3,327)

from USD 49

Chicago 3D Fireworks Cruise

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

4.2

(233)

from USD 52

1 2 3

Top Attractions in Chicago

1 / 2

Attractions

What are people saying about Chicago

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!

Delicious Donuts & City Sights: Chicago's Original Donut 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

Anastasia_F, Sept 2025

Not your average boat tour!

It was so much fun and very informative! I love that the Seadog is a speedboat and takes passengers out onto Lake Michigan, as well as cruises down the river for the architecture tour. Much more fun than your average tour boat!!! Our tour guide H (I can’t recall his name!) was fantastic and kept us entertained the entire time.

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

Alison_P, Sept 2025

Bike tour around Chicago

I had an afternoon to myself and live the outdoors so I booked the 4 hr bike, bites, and brews tour. I had a great time and was completely comfortable doing this tour by self as the guide was great and others in the group very friendly. Not overly strenuous at all, just a decent ride with plenty of stops to learn about Chicago.

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!