Chicago · CRUISES & BOAT TOURS

The 15 Best Boat Trips in Chicago

37 tours  ·  from $28

River or lake, ninety minutes or a whole evening. These 15 cover the architecture boats, the skyline sailings, the dinner decks and the speedboats, each priced, with a note on how much of the time is commentary.

Chicago Architecture River Cruise - The opening view of Chicago’s skyline
Chicago Architecture River Cruises, Chicago Architecture Tours, Cruises & Boat Tours, Tour Reviews

Chicago Architecture River Cruise

1.Chicago Architecture River Cruise

★★★★★★★★★★5.0 · 15,756 reviews · 1 hour to 1 hour 30 minutes (approx.) · from $39Our pick

Cruise from Navy Pier or Michigan Avenue through the Chicago River while an architecture guide explains landmarks, design, and Chicago’s Great Fire. You’ll see the Wrigley Building, Tribune Tower, Hancock Center, Willis Tower, Marina City, and Aqua. Boats have restrooms and a full bar, and dogs are welcome.

“Wonderful excursion with a highly knowledgeable guide. Jim was a terrific guide with real passion for Chicago. His tour alone would make you want to come back.”

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Chicago River: 1.5-Hour Guided Architecture Cruise - Starting near the Michigan Avenue bridge
Chicago Architecture River Cruises, Chicago Architecture Tours, Cruises & Boat Tours, Guided, Tour Reviews

Chicago River: 1.5-Hour Guided Architecture Cruise

2.1.5-Hour Guided Architecture Cruise

★★★★★★★★★★4.8 · 8,046 reviews · 1h 30m · from $44

Cruise Chicago’s main river and both branches for 90 minutes with a live English-speaking guide. You’ll see Marina City, Willis Tower, the Wrigley Building, Aqua, and more, while choosing open-air or climate-controlled seating. Guides such as John, Sarah, Alex, and Scotty D bring humor and solid city context.

“We had a blast. I first did this cruise back in May with my 81 year old dad. Loved it so much that on my return visit to Chicago I brought 11 of my family memebers. So great!”

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Chicago Architecture Center River Cruise aboard First Lady - Boarding at 112 East Wacker Drive
Chicago Architecture River Cruises, Chicago Architecture Tours, Cruises & Boat Tours, Tour Reviews

Chicago Architecture Center River Cruise aboard First Lady

3.Chicago Architecture Center River Cruise aboard First Lady

★★★★★★★★★★5.0 · 5,536 reviews · 1 hour 30 minutes (approx.) · from $57

Spend 90 minutes aboard Chicago’s First Lady with a Chicago Architecture Center docent such as Cynthia, Laura, or Mark. Hear the story behind Marina City, Willis Tower, and more while viewing the skyline from the river. Choose the open deck or heated salon, and buy drinks from the onboard bar.

“Tour was a great length. Very informative. The docent was excellent. Great fun and clear easy delivery.”

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Chicago: Architecture River Cruise Skip-the-Ticket Line - The central river canyon and Chicago’s big names
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Chicago: Architecture River Cruise Skip-the-Ticket Line

4.Architecture River Cruise Skip-the-Ticket Line

★★★★★★★★★★4.8 · 4,325 reviews · 1 hour - 90 minutes · from $39

Cruise all three branches of the Chicago River for 60 to 75 minutes with a live English or Spanish guide. You’ll see Willis Tower, Marina City, Trump Tower, and more, with guides such as Chicago Bob, Juan, Jeremy, and Kevin bringing the buildings to life.

“Enjoyed the cruise, our guide was fun and very informed! Our flight was late and we missed our scheduled time. The company allowed us to move to the next day to be able to use our tickets. Great service!! Thank you!”

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Chicago: 45-Minute Family-Friendly Architecture River Cruise - Boarding near the Wrigley Building
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Chicago: 45-Minute Family-Friendly Architecture River Cruise

5.45-Minute Family-Friendly Architecture River Cruise

★★★★★★★★★★4.7 · 2,304 reviews · 45 min · from $28Best value

Cruise the Chicago River from Lake Shore Drive toward Willis Tower and back with a live English-speaking guide. Expect family-friendly architecture stories, indoor and outdoor seating, local drinks for purchase, and strong sunset or evening photo chances. Guides such as Kenny, Zach, and Alyssa have earned high marks for humor and clear commentary.

“A great boat ride with an extremely knowledgeable tour guide. We had the best time and it was a great way to end our trip!”

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Chicago: 1.5-Hour Lake and River Architecture Cruise - Up the main branch: Chicago’s architecture at close range
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Chicago: 1.5-Hour Lake and River Architecture Cruise

6.1.5-Hour Lake and River Architecture Cruise

★★★★★★★★★★4.7 · 2,050 reviews · 1h 30m · from $44

Cruise from Michigan Avenue to Wolf Point, through the Chicago Lock, and onto Lake Michigan. An English-speaking guide points out landmarks from Marina City and Tribune Tower to Willis Tower and Navy Pier. Choose an open deck or climate-controlled cabin, with snacks and drinks available onboard.

“I really liked the detailed explanations he gave about the view of the city from Lake Michigan and the various buildings seen from the Chicago River.”

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Chicago River 90-Minute Architecture Boat Tour - Willis Tower and Chicago’s Vertical Ambition
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Chicago River 90-Minute Architecture Boat Tour

7.Chicago River 90-Minute Architecture Boat Tour

★★★★★★★★★★5.0 · 1,635 reviews · 1 hour 30 minutes (approx.) · from $37

This 90-minute Chicago River cruise combines open-air skyline views with a covered, air-conditioned cabin. Guides such as David, Hillary, Heath, and Colleen bring Chicago architecture to life with history, engineering facts, humor, and local detail. The boat visits all three major river branches and returns to the starting point.

“I have been on other Chicago River tours, but we covered parts I had not seen before, the southern end towards Chinatown. Having lived in the area and worked in town, I learned new things about my beloved Chicago. Our tour guide was exceptional- a young man from Traverse City, MI. GREAT experience and well worth the price.”

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Lake Michigan Sunset Cruise in Chicago - A quick Chicago River opening
Cruises & Boat Tours, Evening Experiences, Lake Michigan Boat Cruises, Tour Reviews

Lake Michigan Sunset Cruise in Chicago

8.Lake Michigan Sunset Cruise in Chicago

★★★★★★★★★★4.5 · 1,520 reviews · 1 hour 30 minutes (approx.) · from $45

Board at the Wrigley Building for a 90-minute evening cruise along the Chicago River and through the lock to Lake Michigan. Enjoy skyline views as daylight fades, with narration, music, a climate-controlled lounge, restrooms, and a bar serving drinks and snacks for purchase. Arrive early for the best seats.

“I booked this experience for my husband's first weekend after retiring after 40 plus years. This first step in " the best is yet to be" did not disappoint. Despite the large crowd of participants everything flowed smoothly in getting on the boat. The guide was engaging and very knowledgeable. We learned a lot of interesting facts about Chicago history and architecture. The Skyline view at sunset was awesome. The hour and a half flew by.”

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Lake Michigan Skyline Cruise in Chicago - Leaving Navy Pier for open water
Cruises & Boat Tours, Lake Michigan Boat Cruises, Tour Reviews

Lake Michigan Skyline Cruise in Chicago

9.Lake Michigan Skyline Cruise in Chicago

★★★★★★★★★★4.5 · 897 reviews · 30 to 45 minutes (approx.) · from $32

Board Shoreline Sightseeing at Navy Pier for a short Lake Michigan cruise past Willis Tower, the John Hancock Center, Aon Center, Grant Park, Buckingham Fountain, and more. You get recorded commentary, open views, an onboard restroom, and a dog-friendly boat. Bring lunch or buy drinks with cash.

“Not very entertaining and you could not really hear what the narrator was saying. It would be nice to have heat”

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Chicago River Architecture Tour with Small Boat Upgrade Option - The 90-minute route along the Chicago River
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Chicago River Architecture Tour with Small Boat Upgrade Option

10.Chicago River Architecture Tour with Small Boat Upgrade Option

★★★★★★★★★★5.0 · 818 reviews · from $49

Spend about 90 minutes on the Chicago River learning how Art Deco, Gothic, Neoclassical, and modern towers shaped the city. Guides such as Justine and Jim bring the stories to life. Choose a regular boat, a small boat for up to 60 people, or a combo with a 90-minute minibus tour.

“Nice way to see the buildings of Chicago. Speaker talks very fast! Bit difficult to decipher. Supposedly small boat tour. But, not that small. Punctual.”

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Chicago Architectural River Cruise - The guide can make or break the experience
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Chicago Architectural River Cruise

11.Chicago Architectural River Cruise

★★★★★★★★★★4.5 · 804 reviews · 1 hour 30 minutes (approx.) · from $50

Join Chicago Line Cruises at River East Plaza for a 90-minute architectural cruise past more than 50 buildings, bridges, and historic sites. Guides such as Tyler, Valerie, Brian, Jim, and Justine bring Chicago’s rebuilding story to life. Arrive early for the best open-air seats.

“What a lovely trip. Easy to book through Viator. Great communication. Tickets easy to access and cruise very informative.”

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Chicago by Night River and Lake Cruise - Finding First Lady at Michigan Avenue and Wacker Drive
Cruises & Boat Tours, Evening Experiences, Lake Michigan Boat Cruises, Tour Reviews

Chicago by Night River and Lake Cruise

12.Chicago by Night River and Lake Cruise

★★★★★★★★★★4.6 · 791 reviews · from $45

Board First Lady near Michigan Avenue and Wacker Drive for a 90-minute evening cruise along the Chicago River and Lake Michigan. A live English-speaking guide points out Willis Tower, Navy Pier, Buckingham Fountain, and more, while the boat passes through Chicago Harbor Lock.

“We had 1 night in Chicago and thia trip was the the best was to get the most out of the city by night... this was an amazing experience, it's just a shame we were only there for 1 night... we will definitely be back again and this will definitely be on the list again”

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Chicago: Shoreline Lake Michigan Skyline Cruise - What the 30-minute route actually shows you
Cruises & Boat Tours, Lake Michigan Boat Cruises, Tour Reviews

Chicago: Shoreline Lake Michigan Skyline Cruise

13.Shoreline Lake Michigan Skyline Cruise

★★★★★★★★★★4.6 · 758 reviews · 30 min · from $32

From Navy Pier, you’ll cruise north and south along Lake Michigan for broad views of Chicago’s skyline, Willis Tower, the Field Museum, and 360 Chicago. A recorded English or Spanish commentary adds city history and architecture. Arrive early for better seats and bring a jacket.

“such a great informative tour that showed us the wonderful buildings and lake view!”

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Chicago: 1.5-Hour Scenic Sunset Lake Cruise - Cruising the Chicago River before the lake
Cruises & Boat Tours, Evening Experiences, Lake Michigan Boat Cruises, Tour Reviews

Chicago: 1.5-Hour Scenic Sunset Lake Cruise

14.1.5-Hour Scenic Sunset Lake Cruise

★★★★★★★★★★4.7 · 739 reviews · 1h 30m · from $45

Cruise from Michigan Avenue through the Chicago Lock and onto Lake Michigan as the sun drops behind Chicago’s skyline. You’ll see Willis Tower, the John Hancock Building, Grant Park, Soldier Field, Adler Planetarium, and Shedd Aquarium, with brief live commentary and an onboard bar.

“Fantastic boat ride with very good staff. The sunset view was amazing. Thank you.”

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Chicago City Tour with Architecture River Cruise Option - The Loop and the first skyscraper story
Chicago Architecture River Cruises, Chicago Architecture Tours, City Tours, Cruises & Boat Tours, Tour Reviews, Tours

Chicago City Tour with Architecture River Cruise Option

15.Chicago City Tour with Architecture River Cruise Option

★★★★★★★★★★5.0 · 705 reviews · 2 to 4 hours (approx.) · from $49

Ride a climate-controlled minibus through the Loop, Gold Coast, Lincoln Park, and Museum Campus with guides such as Avery, Rick, and Reenie. Add a 75-minute Chicago River cruise for close views of iconic buildings and the story of the river.

“Very informative and an excellent guide on our walk. So much to learn and absorb about your city..thanks Jennifer”

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★ 4.5City Cruises Chicago: 75-min Speedboat Architecture CruiseFrom $61268 reviews

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