Sightseeing Cruises

Chicago Architecture Evening Cruise

Tour boat on Chicago River at sunset, surrounded by tall buildings and orange sky.

DuSable Bridge illuminated at twilight with Chicago skyline in the background.

Boat tour on Chicago River with group, surrounded by modern skyscrapers and bridges.

People on a boat deck viewing Chicago skyline at dusk with water and cloudy sky.

Duration

1 hr 15 min

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.

5.0/5

(21)

Steohen

Sep 2025

Verified booking

5/5

The young man...a college student was very knowledgeable re archetural history style. Our family on tour was my husband, retired building contractor, our daughter and her 9 yr old son who was engaged throughout the 90 min tour. Thank you 😊

Janet

Aug 2025

Verified booking

5/5

We are very happy that we did this cruise! I would say the best cruise I've ever made. Our guide Charlie was a major part in this though. Without him that would only have been half as good.

Admire evening views of Chicago’s skyline from the water, offering a fresh vantage point beyond traditional river cruises.

Cruise past iconic landmarks like Willis Tower, Tribune Tower, and Wrigley Building with stunning views.

Enjoy live or recorded commentary revealing the city's rich architectural history and landmark stories.

Capture incredible photo ops of over 40 architectural marvels bathed in the glow of twilight.

Select either a 75-min cruise departing from Michigan Avenue or a 45-min cruise leaving from Navy Pier.

Commentary in English

75-min evening sightseeing cruise departing from Michigan Avenue (as per tour selected)

45-min evening sightseeing cruise departing from Navy Pier (as per tour selected)

TOTAL DURATION45 minutes
MODE OF TRANSFERBoat
FIRST DEPARTUREHancock Building (875 North Michigan Avenue)
LAST DEPARTUREHancock Building (875 North Michigan Avenue)
1 Boarding point
Navy Pier
Get direction
Sights covered
Hancock Building (875 North Michigan Avenue)
Chicago Lighthouse
Willis Tower
The Museum Campus
Shedd Aquarium
Adler Planetarium
Field Museum of Natural History
Centennial Wheel
Aon Center
Aqua Tower
Field Museum of Natural History
Adler Planetarium
Shedd Aquarium
Chicago Harbor Lighthouse
Lake Point Tower
Grant Park
TOTAL DURATION75 minutes
MODE OF TRANSFERBoat
FIRST DEPARTURETribune Tower
LAST DEPARTURETribune Tower
1 Boarding point
Michigan Avenue
Get direction
Sights covered
Tribune Tower
Lake Point Tower
Centennial Fountain
NBC Tower
Wrigley Building
Trump International Hotel & AMA Plaza Tower
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

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

5
21 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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What our guests say
Graham
Oct 2025
Verified booking
5/5
Fantastic tour, beautiful tour and very informative but in a funny way. Definitely recommend
Cristina
Oct 2025
Verified booking
5/5
The girl who explained all was wonderful
Steohen
Sep 2025
Verified booking
5/5
The young man...a college student was very knowledgeable re archetural history style. Our family on tour was my husband, retired building contractor, our daughter and her 9 yr old son who was engaged throughout the 90 min tour. Thank you 😊
Janet
Aug 2025
Verified booking
5/5
We are very happy that we did this cruise! I would say the best cruise I've ever made. Our guide Charlie was a major part in this though. Without him that would only have been half as good.
Mariano
Aug 2025
Verified booking
5/5
exceptional experience, professionalism and punctuality, to be repeated in the future.

What to bring

Credit card for onboard purchases (no cash accepted).

Light layers or sun/rain protection, especially for boats with open upper decks.

Camera or smartphone for capturing skyline views.

What's not allowed

Outside food and beverages are not permitted on board.

Motorized or oversized wheelchairs are not allowed on most ramps and boats.

Accessibility

Architecture River Tour dock at Navy Pier is wheelchair accessible (for narrow-base wheelchairs only).

Michigan Avenue dock is not wheelchair accessible.

Some boats have restrooms on lower decks that are not accessible due to lack of elevators.

Upper decks are open-air with minimal weather protection.

Additional information

Life jackets are available but will only be distributed in an emergency.

Tours follow local, state, and federal health and safety guidelines.

Most boats are double-decker; some have partial overhead cover, while a few have no cover at all.

Restrooms are available onboard.

Light snacks and beverages are available for purchase.

Leashed dogs are welcome on board.

Your voucher will be emailed to you instantly.

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

Please arrive at the boarding point 15 minutes before the scheduled time of your cruise to avoid any delays.

Boarding point

Please check your final voucher for the boarding point details and specific instructions.