Top Chicago Water Tours

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

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

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!

Chicago River Ghost & Dark History Night Cruise

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

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

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.

Chicago Architecture Center River Cruise aboard First Lady

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

Chicago Lake and River Architecture Tour

Lake Michigan Fireworks Cruise in Chicago

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.

Chicago Sightseeing River and Lake Cruise

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

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

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

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

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.

4.0

(384)

from $63

City Cruises Chicago: River Architectural Lunch Cruise

City Cruises Chicago: River Architectural Lunch Cruise

4.3

(43)

from $85

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

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

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

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

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

Chicago River Sunday Funday Mimosa or Bloody Mary Party Cruise

Chicago All Day Water Taxi

20 minutesFree Cancellation

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

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

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Top Attractions in Chicago

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What are people saying about Chicago

Chicago Sightseeing River and Lake Cruise

Jessicca_A, Sep 2026

Slightly damp but still fun

Be prepared for temp to drop 10-15 degrees as soon as you get out to the harbor/lock area. The seats in the bow are best for less crowds/noise but you will likely get wet if there is any wind or chop at all, and it is known as the Windy City! Wear nonskid shoes for the stairs and bring cash for tips for the crew/bartender.

Chicago Architectural River Cruise

John_B, Sep 2026

The original architecture tour

A very hot day in Chicago so it was OK that the boat had covered lower deck. Otherwise it might’ve been a no go. But the boat was not what was pictured. It was an older boat in the picture that I booked because it looked quaint and different. Staff and amenities on the ship were great, it was cold water, and included soft drinks. Information from the guide to talk to almost an hour and a half about the architecture of the city of Chicago was very good detailed and interesting.

Small-Group Sightseeing Boat Tour in Chicago

Jasyn_H, Aug 2026

Great option for water time.

This was an incredible time. We were looking for something that was a little less crowded but involved the water. Cptn Ken was great and provided. The boat was incredible, he was informative, and we got to see the lake, river and much of the shore. Communication was superb. Well worth the time and no disappointment. Simply book this.

Historical and Architectural Chicago Fireboat River & Lake Cruise

ashleyness45, Aug 2026

Best Tour of Chicago

Absolutely wonderful tour all around. The boat is amazing and the crew was fantastic. We learned so much about the area and history, with lots of laughs from the amazing Cliff. Magic Manny the bartender quenched our thirst the entire time. Great seating options with sun and shade, and plenty of space to walk around the boat. It was our first time to Chicago so we highly recommend this tour to get a great view of the city and learn about the architecture of the amazing city. We loved going thru the lock and river, as well as getting the skyline view from Lake Michigan. 10/10!!

Chicago By Night River and Lake Cruise

Lisa_G, Jul 2026

Very informative and beautiful

Taking the sunset architectural cruise near the Riverwalk was easily one of the highlights of our trip. Seeing the city's iconic skyline transition from the golden hour glow into the beautifully lit evening cityscape is an absolute must-do. The vessel was comfortable, the atmosphere was relaxed, and the tour provided fascinating insights into the history and design behind Chicago's world-famous buildings. If you want a peaceful, breathtaking, and informative way to experience the city from the water, this is it! Highly recommended.

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.

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Jennifer_G, Jul 2026

A+! We loved every minute.

We LOVED our sailing excursion with Captain Ulysses! 6 of us went during a girls weekend, and it was the absolute highlight of our trip. Captain Mike and Captain Ulysses got us on board right on time, and we enjoyed two hours of sailing with great wind and a ton of excitement. If you’re considering booking, DO IT. As a group of moms, we tend to spend our girls trips catching up and reminiscing, and not always making NEW fun memories together. This was exactly what we needed, and we’ll remember this outing forever. We were begging to buy out the next hour, but someone already had it booked. We’d absolutely do it again! Thank you for a great time!

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.

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

Dawn_G, Dec 2025

Worth it!

Love all the information of the buildings’ history! Seeing them in one area was amazing! The tour took about an hour. I didn’t visit the bar/cocoa area downstairs but it’s great that they have one. The guide was funny and friendly. He interacted with us as well. Once trip was over, he stood by to say bye to everyone. I would do it again!

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

Allison_M, Sep 2025

wonderful Windy

This was a lot of fun. The crew was all very engaging but was all business when it was time to raise or lower the sails. Granted we had a perfectly clear and windy day, but the sailing conditions were perfect. As someone from the east coast, it's hard to fathom that we were on a lake, not the ocean. The only complaint was it could have been longer.

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.