Top Chicago Water Tours

Chicago River 90 Minute Architecture Tour

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.

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.

Chicago Architecture River Cruise

1 hour to 1 hour 15 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

Chicago Lake and River Architecture Tour

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 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

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

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

Explore the Chicago River in a unique way with this 120-minute Guided Ghost Tour. Learn about the city's haunted history, including the Great Chicago Fire and the Eastland Disaster. You are welcome to bring your own beverages and food/snacks to fully enjoy your time on the water. Departing from the Chicago Riverwalk, this is a fun and engaging way to experience the spooky side of the city. This tour is typically smaller allowing for you to interact with the tour guide! Ask all the questions, we are ready! - 120-minute ghost tour on the Chicago River for up to 18 passengers - Fun bring-your-own beverage/snacks experience with a u-shaped bar and coolers - Learn about Chicago's haunted history and significant events - Departures from the Chicago Riverwalk—15-minute early arrival required to allow time for check in and depart on time.

Chicago River Guided Ghost Tour

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

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

See the towers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary non-alcoholic refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot buildings that range from Neoclassical to Art Deco, take in over fifty sites, and see the Second City from the water.

Chicago Architectural River Cruise

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 to know the Windy City the easy and comfortable way on a small-group minibus tour. Instead of long walks and navigating public transit, see major landmarks like Museum Campus, Buckingham Fountain, the Magnificent Mile, and Millennium Park from an uncrowded minibus with large picture windows. Your driver and guide knows where to find all the best views, and there are plenty of photo stops along the way.

Chicago City Minibus Tour

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.

from $144

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

Enjoy waterfront views of downtown Chicago on a 2-hour brunch cruise through the heart of the city. Board a luxurious yacht at Navy Pier then relax on deck with a complementary mimosa. Find a comfortable spot on the three climate-controlled observation decks, and enjoy a sumptuous buffet while the onboard DJ spins a leisurely afternoon playlist. Capture unforgettable images of downtown skyscrapers and architectural landmarks as you navigate along the historic shoreline, then loop back and finish your outing at the bustling Navy Pier.

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

3.9

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from $105

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 All Day Water Taxi

20 minutesFree Cancellation

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

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

Experience the ultimate Windy City adventure on Chicago’s luxury guided minibus tour! Explore 20+ top landmarks with curated photo stops at Cloud Gate "The Bean", Museum Campus, & the historic Palmer House. Start at the Palmer House, birthplace of the brownie, & see Frank Lloyd Wright’s work at the Rookery. Pass soaring icons like Willis Tower & Soldier Field while learning the rich history behind each landmark. Hop off at Buckingham Fountain & Museum Campus for views of Lake Michigan, Navy Pier, & the skyline. Pass cultural icons like Shedd Aquarium & the Field Museum. Snap photos beneath "The Bean" at Millennium Park, view the Chicago River, & cruise down the Magnificent Mile past the Water Tower, Gold Coast brownstones, & Playboy Mansion. UPGRADE YOUR TOUR: Select the Architectural River Cruise option at checkout for the ultimate land & river experience! 75-minute cruise offered during summer (April – October) 60-minute cruise offered during winter (November – April)

Luxury Minibus Chicago City Tour with Architecture Cruise Upgrade

Lake Michigan Sunset Cruise in Chicago

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Must-Dos in Chicago

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What are people saying about Chicago

michelle_m, Oct 2026

Solo Vacation Week -KCMO Visitor

I have always wanted to have a fun adventure. My bucket list of my things to do includes riding the Subway Train, Boat Ride on Lake Michigan as the Sun sets and be Solo. It's been a challenging year for me. I lost a family member, a personal friend and a professional colleague of mine. This is my way of honoring my friends and family and celebrating them.

Historical and Architectural Chicago Fireboat River & Lake Cruise

Allison_B, Oct 2026

Fireboat Tour - highly recommended!

Fun and informative! My partner is a Chicagoland native, but had never done such a tour before. We had a blast! The boat was big enough to roam around if you wanted, but small enough to make it feel like a personalized experience. Our tour guide Cliff was fantastic, so knowledgeable and entertaining. Could have spoken with him for hours. So glad we chose this tour over the giant river cruises. Would highly recommend!

Chicago Seadog River & Lake Architectural Tour

Shelli_K, Oct 2026

One of the best tours on the river

This was a fun tour! You start off on Lake Michigan and get a fantastic view of the skyline. Then, you travel through the locks to get to the river. So interesting. Hymie was the best tour guide. He was vey knowledgeable about the history and the buildings. He also knew a lot of trivia about all the places the riders. He said something about each group on board. We felt connected to him because he cared about everyone on his boat.

Chicago By Night River and Lake Cruise

Daleisha_H, Sep 2026

First boat ride

We really had a wonderful time and the scenery OMG absolutely beautiful. The only thing I would suggest is that you either take a small blanket with you or simply dress for the weather. Although they do have an area where you can sit inside and warm up, but to enjoy the full experience and the view definitely sit up top.

Chicago Sightseeing River and Lake Cruise

Adam_R, Sep 2026

So fun so engaging

Full transparency I didn’t have high expectations going in as I decide to do it on a whim with my dad who was visiting, however, this far exceeded my expectations. It was so fun, the guide was so engaging full of really cool facts about the city and the structures. The boat itself is super practical. All in all it was a great time and I plan on doing it again with other out of town friends and family. Thanks again to our guide (I think Liam or Ian) apologies.

Lake Michigan Skyline Cruise in Chicago

Francesco_R, Sep 2026

Awesome View, Fun Boat Ride, and Excellent Narration— Must Try!

This ride does not go out into Lake Michigan; it goes up to the barrier between the port and the rest of the lake. However, it was still a very fun ride. The boat staff are very courteous and professional, and services include drinks and snacks available for purchase. This tour is exactly as the title advertises, for you get to ride out on the lake’s waters while presented with numerous, impressive views of Chicago’s city, especially at sunset where the bright yellow and orange glare shines across and between the building gaps of the city— as if you see a vast silhouette of a city in said glow. Most of the boat ride is smooth, albeit there are a few fun bumps and easy dips. Along with the ride and panorama you get a historical and geographical narration of Lake Michigan and its ties to Chicago. It is a presentation that enriches the experience altogether. Very much worth the price and time!

Chicago City Minibus Tour

Carol_S, Sep 2026

Number one way to start a visit to Chicago

A must for a good introduction to Chicago. This bus stops at multiple tourist sites and allows you time to take photos. The tour guide( Hailey) was so knowledgeable and friendly. I learned a lot about the city from her. I really think this mini bus is the most excellent way to get acquainted with Chicago. The bus is clean and comfortable. Well worth the price. I highly recommend this tour.

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.

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!