Top Chicago Water Tours

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,151)

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

(3,225)

from $28

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

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.

(10,059)

from $45

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 $57

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

(1,555)

from $45

Chicago Lake and River Architecture Tour

(2,339)

from $45

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

Chicago 3D Fireworks Cruise

4.9

(298)

from $47

See Chicago's magnificent skyline at night!

4.2

(233)

from $52

Chicago River 90-Minute Architecture Boat Tour

4.8

(1,659)

from $37

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

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.

(73)

from $105

Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and 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.

(579)

from $46

Chicago Architecture Tour and Speedboat Ride and Lake Michigan

Chicago Seadog River & Lake Architectural Tour

1 hour 15 minutesFree Cancellation

Experience Chicago from the water on a captivating history tour along the iconic Chicago River and Lake Michigan. As you glide through the heart of the city and the Chicago Harbor Lock, expert guides bring the past to life with stories of Chicago’s rise from a frontier town to a world-class metropolis. Discover legendary events like the Great Chicago Fire, marvel at historic landmarks, and gain a deeper appreciation for the maritime history that shaped the city you see today. Travel through the Chicago Harbor Lock and learn about the engineering marvels that reversed the flow of the Chicago River. Learn about how the Chicago Harbor Lock connects the Great Lakes to the Mississippi watershed.

(270)

from $56

Chicago River and Lake Michigan History Boat Tour

Chicago River and Lake Michigan History Boat Tour

1 hour 15 minutesFree Cancellation

5.0

from $46

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 $33

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

(340)

from $36

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

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.

(826)

from $50

Chicago By Night River and Lake Cruise

(325)

from $50

Get a fresher perspective on the Windy City—and a traffic-free one—with this Chicago River architecture cruise. As you pass by some of Chicago's most notable buildings, you'll dine on a 3-course lunch, listening to onboard narration about the city's architecture and history along the way. Unlike your standard walking tour, you can expect comfort, great food, and endless photo opportunities.

City Cruises Chicago: River Architectural Lunch Cruise

City Cruises Chicago: River Architectural Lunch Cruise

4.3

(41)

from $74

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 $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 $50

Chicago Water Taxi River Fireworks Cruise

45 minutesFree Cancellation

4.6

(10)

from $25

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

5.0

from $57

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

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!

3.9

(357)

from $63

Chicago River Ghost & Dark History Night Cruise

Chicago River Ghost & Dark History Night Cruise

Historical and Architectural Chicago Fireboat River & Lake Cruise

4.1

(121)

from $46

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What are people saying about Chicago

toddweitzel, May 2026

Unique and awesome way to see the Chicago river

Had a great time with family cruising on a piece of Chicago history. Smaller boat (ie less people) than the larger boats cruising the river. Great narrator in Cliff! If you’re dead set on being in the sun, you need to get there early and get the seats on the bow. My kids are pretty picky and even they said they enjoyed their time on the river.

Chicago By Night River and Lake Cruise

Crawford_W, May 2026

Phenomenal.

Very memorable. Every staff member performed top tier, from the bartenders to the host who informed us of the Chicago buildings! And we can’t forget the greeters, the staff who was on the street directing us to where we’ll be boarding. And last, but never least, the captain who steered so beautifully 🙏🏾❤️💯! Everyone gets AAAAA’s!

Chicago Architectural River Cruise

Heidi_W, Apr 2026

This is the best way to...

This is the best way to acclimate yourself to Chicago. We learned so much from the tour guide and used what we learned all weekend long. The crew was amazing and professional and the complementary drinks especially he hot chocolate was much needed on this cold afternoon.

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 Seadog River & Lake Architectural Tour

Steve_S, Sept 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

Sian_S, Sept 2025

Outstanding Value

Fantastic trip for a very reasonable price. The host was friendly and knowledgeable and made the trip a real pleasure. We were delighted to find this trip also included the city river tour in the price. One very slight improvement would be to make the location a little better signposted but we would definitely book again.

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Kira_M, Jul 2025

Best Part of Our Trip

We took a two hour sail for our daughter’s 24th birthday. It was fantastic! Everyone in the family felt like it was the best part of our vacation. Captain Mike was awesome and answered all kinds of questions about sailing and some Chicago history. I cannot recommend this enough!