Top Chicago Water Tours

Chicago River 90-Minute Architecture Tour

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.

(10,600)

from $45

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,689)

from $39

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

(3,447)

from $28

Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel (with an enclosed and climate-controlled lounge) in the heart of the Magnificent Mile, and cruise along the Chicago River. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.

Lake Michigan Sunset Cruise in Chicago

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.

(1,635)

from $45

Chicago Architecture Center River Cruise aboard First Lady

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

4.9

(6,629)

from $57

Chicago Lake and River Architecture Tour

This tour cruises the Chicago River 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.

(2,396)

from $45

Chicago Architecture Tour and Speedboat Ride and Lake Michigan

Chicago Seadog River & Lake Architectural Tour

1 hour 15 minutesFree Cancellation

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.

(280)

from $42

Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

(666)

from $46

Lake Michigan Fireworks Cruise in Chicago

2 to 3 hours

4.2

(133)

from $55

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.

Chicago By Night River and 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!

(399)

from $50

Chicago River Ghost & Dark History Night Cruise

Chicago River Ghost & Dark History Night Cruise

4.1

(172)

from $46

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.

The Chicago River, as seen from our stop on wacky Wacker Drive

Chicago City Tour with Architecture River Cruise Option

2 to 4 hoursFree Cancellation

4.8

(731)

from $50

Chicago River Floating Tiki Bar Cruise Friday & Saturday

1 hour 15 minutes

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).

(7)

from $42

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

4.4

(940)

from $34

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

Admire up-close views of the Chicago skyline—and a fireworks show over the city—on this tiki bar boat tour. In the evening, make your own way to the departure point at the Chicago Riverwalk, hop aboard, and get comfortable in the air-conditioned seating area or on the deck. Purchase cocktails and food from the on-site tiki bar, watch the city float by, and then sit back and take in the show.

(842)

from $50

Chicago River Spectacular Fireworks Show and Tiki Bar Cruise

Chicago River Spectacular Fireworks Show and Tiki Bar Cruise

1 hour 30 minutes

3.9

(29)

from $53

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

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.

5.0

(12)

from $65

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

(412)

from $47

Small-Group Sightseeing Boat Tour in Chicago

Small-Group Sightseeing Boat Tour in Chicago

5.0

(106)

from $89

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

Chicago 3D Fireworks Cruise

5.0

(72)

from $508

Per group

Chicago River Tiki Bar Party Cruise from Chicago River Wednesdays

4.2

(257)

from $52

1 hour 15 minutes

4.0

(123)

from $42

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 spectacular fireworks display at Navy Pier. This 1.5-hour cruise offers a unique perspective of the city while providing a relaxed atmosphere for friends and family to gather and enjoy the show. Boarding begins 15 minutes prior to departure, so arrive early to secure your spot and make the most of this dazzling experience. - 1.5-hour cruise featuring panoramic views of Chicago's skyline - Marvel at the iconic fireworks show off Navy Pier - Departing and returning to 111 N Lake Shore Drive

Chicago Fireboat Fireworks Cruise

4.6

(13)

from $57

Chicago Water Taxi River Fireworks Cruise

45 minutesFree Cancellation

Historical and Architectural Chicago Fireboat River & Lake Cruise

(12)

from $25

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Top Attractions in Chicago

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What are people saying about Chicago

Daniell_S, Jul 2026

Very relaxing and well worth the money

This was a lot of fun and very knowledgeable. There is a parking lot nearby that is reserved for the boat cruises. It showed full when we went at noon but we asked and they let us in. This was very relaxing and you got to see the architecture up close. Would definitely do again.

Chicago's Fireworks Show aboard Tall Ship Windy!

Chris_T, Jul 2026

A great trip aboard the...

A great trip aboard the tall ship Windy. The fireworks display was well worth waiting for and highly recommended! And afterwards I was one of the 4 volunteers who helped raise the mast (quite an enjoyable experience) for us to sail around before returning. The crew were very accommodating. Altogether a quite relaxing time really.

Chicago By Night River and Lake Cruise

Gabrielle_B, Jul 2026

Pleasant Suprise!

This was a wonderful experience. We chose the First Lady as a last‑minute excursion to close out our vacation, and it ended up being a highlight of our trip. The crew was friendly, professional, and exceptionally knowledgeable.I highly recommend taking the evening tour being out on the lake and river while the city lights reflect off the architecture creates an unforgettable atmosphere. It’s the perfect blend of learning about Chicago’s rich history and enjoying a relaxing, scenic experience.The gentleman leading the tour did an excellent job balancing insightful information with moments for us to take photos and simply enjoy the view, ensuring we never missed anything important.We can’t wait to do this again on our next visit. Well done 😊

Chicago CityPASS®

Dana_R, Jul 2026

Loved the City pass and...

Loved the City pass and the expedited lines that allowed us to make the most of our time in Chicago (no waiting in long lines). We had 5 days to see the sites and were able to plan all of our activities before we even arrived in Chicago. We stayed at the Sheraton Grand Riverwalk near Navy Pier over July 4th weekend.

Small-Group Sightseeing Boat Tour in Chicago

Carolina_M, Jul 2026

Thrilling and Beautiful

Thrilling and beautiful suitable for all ages Shows off Chicago and her history. Captain Ken has a charming personality and a great knowledge of Chicago. It is a little difficult to find but despite us being late he gave us the full tour. We would do this trip again if in Chicago PS When you reach the harbour Captain Ken can be found at Peir A

Chicago Seadog River & Lake Architectural Tour

ROMANA_K, Jun 2026

Speed boat ride in Chicago

This was fantastic experience from the start to finish! We did the 7:15 pm ride and it was the best time to do it in June. It was hot during the day but for the 7:15 pm ride the weather was much cooler which felt great! We boarder and finished at the Navy Pier. The pier is great to walk, have drink and food and enjoy some live music! It is fun amusement place! First we went on the river to downtown which was awesome! So informative and spectacular to see all the buildings!!! Wow! To see the buildings from the river and considering that it was slowly getting to sunset hour, I would do it again in a heartbeat! The reflection of the sun going down on the buildings at different angles was incredible! After the river Seadog team took us on the speed boat on the lake when Sun completed its sunset! We went fast on the boat, water splashing, music playing and everyone was laughing and having so much fun! IT WAS the BEST THING we did in Chicago! Book your tickets for the 7:15pm only with Seadog Speed Boat! The time of the ride and the company matters very much for the experience. And the boat is smaller than the other ones from other companies so we were smaller group of people given great fun and informative experience from the Crew! Thank you SEADOG! We love it!😍

Chicago Architectural River Cruise

Marcia_H, May 2026

Architectural river boat cruise

The Chicago Riverboat Architecture tour is a must do if you travel to or live near Chicago. I have taken these tours in past years when I lived in the city, and I’m always impressed with and proud of Chicago’s international renowned reputation regarding historic building architecture as well as the recent and ongoing architectural achievements that make up Chicago’s downtown and skyline. The tour I booked via Viator was excellent because of the docent’s knowledge of Chicago’s building history and architectural significance. I highly recommend this tour!

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Amena_S, Apr 2026

Top tier experience

It was amazing from start to finish. Very aesthetically pleasing and service and food was top tier. Our server Heather was a perfect 10 across the board. Her recommendations, her spirit, her genuine energy was a breath of fresh air. She helped us with food selections, which were amazing down to photo opportunities. She even led us to the amazing bartender Keisha who made the best bottomless mimosas to say the least. We had to stop by the bar to let Ms Keisha know how well she mixed those cocktails. This was truly an amazing birthday brunch experience. Great way to start my birthday!!!

Chicago City Tour with Architecture River Cruise Option

Marty_R, Mar 2026

Wonderful tour with Alan!

Alan was a great tour guide - lots of fun information and entertained all of our questions. It was my 17 year old daughter’s first trip to Chicago, so I wanted her to get to see as much of the main parts of the city as possible, and we definitely hit all the ones I had on my list! The bus itself was clean and well cared for, and I like that it was smaller than the other buses because it made it much more personal. Alan also had great recommendations for places to go, where to eat, and was able to give ideas for spots that were of interest to us specifically. Highly recommended!