Top Chicago On the Water

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 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).

(3,186)

from $28

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

4.4

(910)

from $33

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.

Chicago Architecture River Cruise

1 hour to 1 hour 30 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.

(16,060)

from $39

See Chicago's magnificent skyline at night!

Chicago By Night River and 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.

4.5

(311)

from $50

Historical and Architectural Chicago Fireboat River & Lake 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!

4.9

(273)

from $47

Chicago River Ghost & Dark History Night Cruise

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.

4.1

(113)

from $46

Chicago River 90-Minute Architecture Tour

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

(9,971)

from $45

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.

4.6

(69)

from $85

Chicago Architectural River Cruise

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.

(821)

from $50

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

3.9

(355)

from $63

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.

(2,332)

from $45

Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

(570)

from $46

Chicago River 90-Minute Architecture Boat Tour

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!

(1,649)

from $37

Chicago River Cycleboat Cruise

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.

5.0

(8)

from $65

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

4.9

(5,863)

from $57

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.

Chicago Seadog River & Lake Architectural Tour

1 hour 15 minutesFree Cancellation

4.5

(265)

from $48

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.

Lake Michigan 30-Minute Speedboat Ride

30 minutesFree Cancellation

4.1

(337)

from $36

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 buffet and bottomless mimosas while in our comfortable indoor areas. Marvel at unparalleled views of Chicago’s iconic landmarks, such as Willis Tower and Navy Pier from inside or enjoy fresh breezes on the open-air decks. This fun-filled brunch cruise experience for all ages is complete with lively DJ entertainment, dancing, games, and a fully stocked cash bar. Elevate your weekend plans with a one-of-a-kind brunch cruise on the water!

City Cruises Chicago: Signature Brunch Cruise on Lake Michigan

Enjoy a memorable, one-of-a-kind night out on Lake Michigan aboard this combination dinner, dancing, and sightseeing cruise. Make your own way to Navy Pier, and set off as the evening begins. You can admire views of Chicago’s picture-perfect skyline as the sun starts to set. While on board, take advantage of the all-you-can-eat buffet dinner, drinks to purchase, a DJ-helmed soundtrack, and even a fireworks display (weather permitting).

4.0

(4)

from $101

City Cruises Chicago: Fireworks Signature Dinner Cruise

2 to 3 hoursFree Cancellation

3.9

(85)

from $128

Set sail for an unforgettable experience on the water with private boat tours and captained rentals along the Chicago River and Lake Michigan. Whether you're looking to explore the city’s historic waterways or enjoy a relaxing cruise with skyline views, we’ve got you covered. Cruise past iconic landmarks like the Wrigley Building on the Chicago River before heading out to Lake Michigan, where you'll take in panoramic views of the city’s world-famous skyline. With a comfortable and stylish cruiser boat, every ride is smooth, scenic, and uniquely Chicago. Want a custom experience? Choose a private boat rental with a licensed captain—ideal for birthdays, date nights, family outings, or simply relaxing with friends. You enjoy the moment, and we handle the navigation. No boating experience needed. Just bring your favorite snacks, drinks, and good vibes—we’ll provide the boat, the captain, and the unforgettable views. Book now and experience Chicago like never before—from the water!

Chicago Private Boat Tours

2 to 8 hoursFree Cancellation

4.4

(7)

from $299

Per group

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.

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

1 to 2 hoursFree Cancellation

Enjoy a celebratory way to sightsee—and a river cruise like no other—with this evening excursion along the Chicago River. Your modern, glass-enclosed boat makes for a comfortable ride, no matter the weather—and gives panoramic views of Chicago’s well-known architectural gems. As you go, indulge in a gourmet, multi-course meal while enjoying live entertainment, including a DJ and fireworks displays on Wednesdays and Saturdays.

(23)

from $40

City Cruises Chicago: Fireworks Premier Plus Dinner Cruise

2 to 3 hoursFree Cancellation

3.8

(5)

from $169

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

2 to 4 hoursFree Cancellation

(719)

from $50

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

1 hour 15 minutes

Delicious Donuts & City Sights: Chicago's Original Donut Tour

(20)

from $91

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Top Attractions in Chicago

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What are people saying about Chicago

Lindsey_S, Mar 2026

Donut miss this tour!!!

This was such a fun morning! Nick was engaging, funny and knowledgeable about the shops we visited and sites of downtown. We got to see several new parts of Chicago we hadn't seen yet, and sample some absolutely delicious donuts until we were completely stuffed - you won't go hungry on this tour and we even took some leftovers for the road! Thanks for making our last morning in Chicago GREAT!

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, Sep 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, Sep 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

Stephanie_P, Jun 2025

Amazing! Highly recommend!

This adventure was the highlight of our trip. Captain Ken was amazing and so knowledgeable. We learned so much about Chicago’s history and had a wonderful time out on the water. We always felt very safe as he is very skilled at what he does. Captain Ken is super funny which was a bonus! We would definitely re book with him.