Top Chicago Water Tours

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

(16,066)

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

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.

(3,188)

from $28

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

4.9

(5,873)

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

(2,333)

from $45

Chicago River 90-Minute Architecture Boat Tour

Chicago 3D Fireworks Cruise

(1,649)

from $37

See Chicago's magnificent skyline at night!

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

4.2

(231)

from $52

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.

4.6

(69)

from $85

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

(312)

from $50

Chicago Architectural River Cruise

Chicago Water Taxi River Fireworks Cruise

(822)

from $50

45 minutesFree Cancellation

4.6

(10)

from $25

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

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

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.

(571)

from $46

Chicago River and Lake Michigan History Boat Tour

1 hour 15 minutesFree Cancellation

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

from $46

Happy Hour Fireboat 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).

from $80

Per group

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

4.4

(910)

from $33

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

(8)

from $65

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!

1 hour 30 minutes

City Cruises Chicago: Seadog Fireworks Cruise

(14)

from $114

1 hourFree Cancellation

4.3

(24)

from $60

Chicago Architecture River Tour & Hop-on Hop-off Sightseeing Tour

4.2

(39)

from $99

Soak up unbeatable views of Lake Michigan and the Chicago skyline—and stay on the water long enough to watch the lights come on in the city—on this private, sunset sailing tour. This charter is completely customizable, giving you the chance to choose your music, route, and up to five additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side, all led by US Coast Guard–certified captain.

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

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.

(27)

from $508

Per group

City Cruises Chicago: Fireworks Premier Plus Dinner Cruise

2 to 3 hoursFree Cancellation

3.8

(5)

from $169

Chicago River Sunday Funday Mimosa or Bloody Mary Party Cruise

1 hour 30 minutes

4.2

(27)

from $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

Historical and Architectural Chicago Fireboat River & Lake Cruise

(95)

from $89

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What are people saying about Chicago

Richard_H, May 2026

A great tour on a piece of Chicago history

This was a very informative and fun tour. You got to ride on a real piece of Chicago history while learning about the the very diverse architecture of this city. I lived here as a kid/young adult never knew we had a lock between the river and the lake. 🤯. The tour guide was funny and knowledgeable. He answered all our questions and gave us lots of little gems. I learned some things on this tour that I had not heard of on other boat tours. They had a full bar with hot and cold drinks. Bartender was great and made good drinks. Two bathrooms on board. Was a very enjoyable experience. I would highly recommend this tour if you are looking to do a boat tour.

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 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 Sightseeing River and Lake Cruise

Natasha_P, Oct 2025

Views and lots of architectural information

On time departure. First went into Lake Michigan and then up the Chicago River before docking again. A lot of interesting information about the architecture and the guide was entertaining and fun to listen to. Sunset time was perfect. Drinks available for purchase.

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!