Top Chicago Water Tours

Chicago River 90-Minute Architecture Tour

(10,000)

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

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.

(3,191)

from $28

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

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.

(16,075)

from $39

Chicago Architecture Center River Cruise aboard First Lady

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

4.9

(5,883)

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

4.5

(1,545)

from $45

Chicago Lake and River Architecture Tour

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.

(2,333)

from $45

Historical and Architectural Chicago Fireboat River & Lake Cruise

Historical and Architectural Chicago Fireboat River & Lake 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.

4.9

(278)

from $47

See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

4.5

(314)

from $50

Chicago River 90-Minute Architecture Boat Tour

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.

(1,650)

from $37

Chicago Architectural River Cruise

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

(822)

from $50

Chicago 3D Fireworks Cruise

4.6

(69)

from $94

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.

4.2

(231)

from $52

Chicago Architecture Tour and Speedboat Ride and Lake Michigan

Chicago Seadog River & Lake Architectural Tour

1 hour 15 minutesFree Cancellation

4.5

(265)

from $48

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

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.

(719)

from $50

Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

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).

(571)

from $46

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

4.4

(910)

from $33

Chicago Water Taxi River Fireworks Cruise

45 minutesFree Cancellation

4.6

(10)

from $25

Chicago River and Lake Michigan History Boat Tour

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.

Chicago River and Lake Michigan History Boat Tour

1 hour 15 minutesFree Cancellation

5.0

from $46

City Cruises Chicago: Seadog Fireworks Cruise

1 hourFree Cancellation

4.3

(24)

from $55

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a leisurely evening sail past the brilliant and beautiful Chicago nighttime skyline. Windy provides the accompanying sound track, over the ship sound system coordinated fireworks display, amazing show! Rain or Shine event. no umbrellas are allowed to be opened underway. Tall Ship Windy, located on Navy Pier, and we have a ticket booth and dock, in front of the Billy Goat Bar and Grill. Arrive early, as fireworks crowds are huge! expect travel delays.

Chicago's Fireworks Show aboard Tall Ship Windy!

Chicago's Fireworks Show aboard Tall Ship Windy!

1 hour 30 minutes

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!

(14)

from $114

Chicago River Ghost & Dark History Night Cruise

Chicago River Ghost & Dark History Night Cruise

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.

4.1

(113)

from $46

City Cruises Chicago: River Architectural Lunch Cruise

City Cruises Chicago: River Architectural Lunch Cruise

4.3

(41)

from $74

Take part in a unique evening Happy Hour Cruise, featuring fresh craft beers while cruising the stunning Chicago skyline. Every Thursday and Friday evening, this 2-hour experience begins on Lake Michigan, sails through the locks, and navigates the Chicago River, providing breathtaking views and delightful sunsets. On Thursdays, a representative from Phase Three Brewing will be onboard to share insights about their innovative ales and lagers, enhancing your tasting experience. On Fridays, we showcase live music. This cruise is exclusively for adults 21 and older, making it the perfect outing for beer enthusiasts looking to unwind in a vibrant setting. - Enjoy a 2-hour sunset cruise - Cruise through Lake Michigan and downtown Chicago's iconic skyline - Exclusively for adults 21 and over, ensuring a mature atmosphere

Happy Hour Fireboat Cruise

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

5.0

from $80

Per group

from $144

1 2

Top Attractions in Chicago

1 / 2

Attractions

What are people saying about Chicago

Historical and Architectural Chicago Fireboat River & Lake Cruise

Karla_S, May 2026

Don’t Miss This One!

What a wonderful tour! I highly recommend! Smaller boat, with history, made this so much more intimate than being on one of the normal Chicago River boats jammed with people. And you get to see the skyline from the lake as well as experience the river. Don’t miss this one! And……. our guide, Cliff was awesome!

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.

Chicago Sightseeing River and Lake Cruise

Micheal_B, Oct 2025

Great tour of Chicago river and Lake Michigan

This is a fantastic river and lake tour that gives you great insight into the architecture of Chicago and some of its history. Our guide Hayley was fantastic (as was Mary Jo at the bar). Informative, fun, engaging — a great way to see some of Chicago!

Chicago By Night River and Lake Cruise

Tracy_V, Oct 2025

Unforgettable!

Absolutely breathtaking!!! Pictures are beautiful but there are no words to describe the night cruise, it’s one of a kind! Book your night cruise, and post your word to describe! Haiku our tour guide was amazing, knowledgeable, funny and friendly! Thank you for sharing Chicago’s history with all of us.

Chicago River 90-Minute Architecture Boat Tour

Noreen_S, Oct 2025

As out of state visitors,...

As out of state visitors, learning about Chicago’s history, and particularly the architecture that has evolved since the Great Fire, was a great introduction to Chicago. The boat tour was a great way to see the city and its history. David was a fantastic docent, extremely knowledgeable, engaging, informative and humorous. Already recommended this to my daughter.

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Stephany_G, Oct 2025

perfect, 10/10 experience

My friend and I went and it was seriously the best time. the food was really good and the service was amazing. The waiters kept the mimosas full at all times! there’s also a deck at the front of the boat to go and enjoy the views and take some pictures. Seriously a 10/10 experience! Will be coming back for sure.

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!

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!

City Cruises Chicago: River Architectural Lunch Cruise

Donna_G, Jun 2025

Excellent excursion

The staff on board was very friendly and helpful from start to finish. Our server, Heather, provided outstanding service, and shared local tips for us. We appreciated everything she did for us. The cruise itself was comfortable and enjoyable. We learned quite a bit along the way. The link for directions to the meeting point that Viator provided was inaccurate; it brought us to the NBC building. This was problematic and stressful. We tried contacting the tour operator via the chat feature to ask for help, but we never received a response. This was also problematic. We only managed to locate the meeting location because we allowed a lot of extra time to do so. Both Viator and the tour operator need to do better. I am tempted to give only four stars to make that point, but I am opting instead to rate the tour and staff. I hope this review will prompt them to look into these issues.