Sightseeing Cruises

Chicago River Architecture Cruise

Chicago River cruise with tourists viewing city skyline and architecture.

Chicago River with skyscrapers at sunrise in downtown Chicago.

Chicago River cruise boat passing downtown skyscrapers.

Person on a boat enjoying the Chicago River Architecture Tour with city skyline views.

Duration

45 mins - 1 hr 30 mins

Free cancellation

Free cancellation up to 24 hours before the start of your experience

Book now, pay later

Book now without paying anything. Cancel for free if your plans change.

Guided tour

4.8/5(432)

Tiffany G

Group

Verified booking

5 days ago

Our 45-minute Chicago River Architecture Cruise with Wendella was one of the highlights of our trip! The views of the city's iconic skyline were absolutely stunning, and seeing Chicago from the river gave us a whole new appreciation for its incredible architecture and history. The tour guide was engaging, knowledgeable, and made the experience both informative and entertaining. Even though it was only 45 minutes, it was packed with fascinating stories about the buildings and the city's rich architectural heritage. The boat was clean, comfortable, and well-organized, making the entire experience relaxing and enjoyable. Whether it's your first time in Chicago or you're visiting again, this cruise is definitely worth it. Highly recommended for anyone looking to experience the beauty of the city from a unique perspective!

Heather S

Couple

Verified booking

5 days ago

Very informative and great views! We enjoyed seeing everything at night and took some great pictures along the way. Our tour guide was great. He was both informative and entertaining!

Nael M

Family

Verified booking

5 days ago

“I absolutely love this place! The service is top-notch, and I highly recommend everyone to come here. I like it so much, and it really exceeded my expectations

Allison G

Family

Verified booking

Last week

Excellent tour! The views were spectacular, and our guide was incredibly knowledgeable, providing interesting information about each of the buildings along the way. My only suggestion would be for the tour staff to remind guests to be mindful of others when taking photos. During the tour, a large family stood at the front the entire time while taking pictures, making it difficult for others to enjoy the views and capture their own photos. It was a bit frustrating, but aside from that, the experience was fantastic. I would definitely recommend this tour!

Adam G

Couple

Verified booking

Last week

Really enjoyable. Entertaining guide. Informative. Note: It was particularly sunny out and so as we were boarding the very full cruise we had the opportunity to sit on the deck, but we opted to go sit down below despite a few seats still being available. What we didn't realize is that (obviously) they'd be talking about things on either side of the boat so from our vantagepoint we were only able to take-in 50% of what was being pointed out. Still enjoyable -- just a warning to get more out of the experience than we did.

Mason C

Group

Verified booking

Jun 2026

The Chicago River Architecture Cruise through Wendella and Headout was a great experience overall. Booked for a work team building and culture event and the group had a great time on the cruise connecting and enjoying the tour. The process was easy from purchase to day-of boarding. Highly recommend booking for your next team event.

Discover Chicago's architectural wonders on a guided cruise along the Chicago River with live commentary.

As you set sail, enjoy insights from your local guide on Chicago's architectural heritage.

Take the cruise to gain a deeper appreciation of Chicago's legacy by exploring its most famous landmarks from a unique vantage point on the river.

See over 50 landmarks, including the Wrigley Building, Chicago Riverwalk, Michigan Avenue Bridge, and Willis Tower, offering a blend of educational insights and comfort.

Choose to upgrade from a 45-min cruise to a 60-min or a 90-min cruise for a more in-depth exploration of Chicago's history.

45-minute narrated architecture boat tour along the Chicago River (as per option selected)

60-minute narrated architecture boat tour along the Chicago River (as per option selected)

90-minute narrated architecture boat tour along the Chicago River (as per option selected)

Expert English-speaking guide

Access to the upper deck for fresh air and views

Access to the climate-controlled lower deck lounge

Full-service bar onboard (available for purchase with a valid ID)

Food and beverages (available for purchase at the bar)

Parking fees

Refunds or transfers after the scheduled departure time

Gratuities

TOTAL DURATION45 minutes
1 Boarding point
Wendella's Michigan Avenue Docks
Get direction
Sights covered
London Guarantee Building
Carbide and Carbon Building
Crain Communications Building
35 East Wacker
Leo Burnett Building
77 West Wacker
Chicago Riverwalk
LaSalle/Wacker Building
333 West Wacker
Civic Opera Building
CME Center
Willis Tower
2 North Riverside Plaza
100 N Riverside Plaza
150 N Riverside Plaza
River Point
Merchandise Mart
Reid-Murdoch Center
Marina City
AMA Plaza
Trump International Hotel & Tower
Wrigley Building
Tribune Tower
NBC Tower
Centennial Fountain
Lake Point Tower
TOTAL DURATION1 hour 15 minutes
MODE OF TRANSFERBoat
2 Boarding points
Michigan Avenue
Get direction
Navy Pier
Get direction
Sights covered
Tribune Tower
Lake Point Tower
Centennial Fountain
NBC Tower
Wrigley Building
Trump International Hotel & Tower
AMA Plaza
Marina City
Reid-Murdoch Center
Merchandise Mart
Wolf Point Development
River Point
333 West Wacker
Chicago Riverwalk
77 West Wacker
Leo Burnett Building
35 East Wacker
Carbide and Carbon Building
London Guarantee Building
Crain Communications Building
Aon Center
Aqua Tower
Chicago Marine Safety Station
TOTAL DURATION1 hour 30 minutes
1 Boarding point
Wendella's Michigan Avenue Docks
Get direction
Sights covered
Lake Point Tower
Centennial Fountain
NBC Tower
Tribune Tower
Wrigley Building
Trump International Hotel & Tower
AMA Plaza
Marina City
Merchandise Mart
Reid-Murdoch Center
Residences at River Bend
Kinzie Park
River Point
150 N Riverside Plaza
100 N Riverside Plaza
2 North Riverside Plaza
Old Post Office
Union Station Power House
Canal Street Railroad Bridge
River City
The Southbank
311 South Wacker
Willis Tower
Chicago Board of Trade
CME Center
Civic Opera Building
333 West Wacker
LaSalle/Wacker Building
Chicago Riverwalk
77 West Wacker
Leo Burnett Building
35 East Wacker
Carbide and Carbon Building
London Guarantee Building
Aon Center
Aqua Tower
Vista Tower
Crain Communications Building
Chicago Marine Safety Station
Goose Island
The Domain

You can cancel these tickets up to 24 hours before the experience begins and get a full refund.

432 reviews
How do we collect reviews?
These ratings include verified reviews from both Headout guests and our trusted partners who operate this experience locally. All reviews come from real travelers who've taken this experience.
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Guests from Canada, Mexico, Ireland and over 33 countries have loved this experience
What our guests say
Tiffany G
Group
Verified booking
5 days ago
Our 45-minute Chicago River Architecture Cruise with Wendella was one of the highlights of our trip! The views of the city's iconic skyline were absolutely stunning, and seeing Chicago from the river gave us a whole new appreciation for its incredible architecture and history. The tour guide was engaging, knowledgeable, and made the experience both informative and entertaining. Even though it was only 45 minutes, it was packed with fascinating stories about the buildings and the city's rich architectural heritage. The boat was clean, comfortable, and well-organized, making the entire experience relaxing and enjoyable. Whether it's your first time in Chicago or you're visiting again, this cruise is definitely worth it. Highly recommended for anyone looking to experience the beauty of the city from a unique perspective!
Allison G
Family
Verified booking
Last week
Excellent tour! The views were spectacular, and our guide was incredibly knowledgeable, providing interesting information about each of the buildings along the way. My only suggestion would be for the tour staff to remind guests to be mindful of others when taking photos. During the tour, a large family stood at the front the entire time while taking pictures, making it difficult for others to enjoy the views and capture their own photos. It was a bit frustrating, but aside from that, the experience was fantastic. I would definitely recommend this tour!
Adam G
Couple
Verified booking
Last week
Really enjoyable. Entertaining guide. Informative. Note: It was particularly sunny out and so as we were boarding the very full cruise we had the opportunity to sit on the deck, but we opted to go sit down below despite a few seats still being available. What we didn't realize is that (obviously) they'd be talking about things on either side of the boat so from our vantagepoint we were only able to take-in 50% of what was being pointed out. Still enjoyable -- just a warning to get more out of the experience than we did.
Margaret B
Group
Verified booking
3 weeks ago
We took Strake Jesuit Quiz Bowl Teams on the River Cruise. The students and teachers loved the boat, the guide, and the fabulous views. We had a wonderful cultural experience! I highly recommend Wendella Tours; this experience really made a good memory for our students. Next year, we hope to go on the 90 minute tour.
Deanna D
Solo
Verified booking
3 weeks ago
We took my son's pre-school class and they had a blast! The guide was extremely knowledgable but also entertaining and funny. I would recommend this for fieldtrips, bring your out of town guests to see our city's beautiful landscape or great for datenight. 10/10

What to bring

Carry a valid photo ID for ticket verification.

Dress according to the weather and consider bringing sunscreen if needed.

What’s not allowed

Outside food and alcohol are not permitted onboard.

Weapons of any kind are strictly prohibited on the cruise.

Accessibility

The tour is wheelchair accessible from the West Dock.

Select boats feature an elevator between decks.

ADA-compliant restrooms are available onboard.

Additional information

All bags are subject to mandatory security screening.

Children under 4 can ride for free.

Snacks and beverages are available for purchase on board.

The tour operates rain or shine, with most boats offering climate-controlled indoor seating.

Guests should arrive 45 minutes before departure, with boarding typically starting 15 to 30 minutes prior.

Your voucher will be emailed to you shortly.

Display the voucher on your mobile phone with a valid photo ID at the starting point.

Please check your final voucher for the starting point details & specific instructions.