Processing your payment

Headout logo. Link to home.
Help
Sightseeing Cruises

Chicago Architecture Evening Cruise by Shoreline

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.

Meals included

Indulge in a sumptuous meal as a part of your experience
    • Commentary in English

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

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

  • TOTAL DURATION45 minutes
    MODE OF TRANSFERBoat

    1 Boarding point

    Navy Pier

    Get direction

    Sights covered

    Hancock Building (875 North Michigan Avenue)

    Hancock Building (875 North Michigan Avenue)

    Chicago Lighthouse

    Chicago Lighthouse

    Willis Tower

    Willis Tower

    The Museum Campus

    The Museum Campus

    Shedd Aquarium

    Shedd Aquarium

    Adler Planetarium

    Adler Planetarium

    Field Museum of Natural History

    Field Museum of Natural History

    Centennial Wheel

    Centennial Wheel

    Aon Center

    Aon Center

    Aqua Tower

    Aqua Tower

    Field Museum of Natural History

    Field Museum of Natural History

    Adler Planetarium

    Adler Planetarium

    Shedd Aquarium

    Shedd Aquarium

    Chicago Harbor Lighthouse

    Chicago Harbor Lighthouse

    Lake Point Tower

    Lake Point Tower

    Grant Park

    Grant Park

    TOTAL DURATION75 minutes
    MODE OF TRANSFERBoat

    1 Boarding point

    Michigan Avenue

    Get direction

    Sights covered

    Tribune Tower

    Tribune Tower

    Lake Point Tower

    Lake Point Tower

    Centennial Fountain

    Centennial Fountain

    NBC Tower

    NBC Tower

    Wrigley Building

    Wrigley Building

    Trump International Hotel & AMA Plaza Tower

    Trump International Hotel & AMA Plaza Tower

    Marina City

    Marina City

    Reid-Murdoch Center

    Reid-Murdoch Center

    Merchandise Mart

    Merchandise Mart

    Wolf Point Development

    Wolf Point Development

    River Point

    River Point

    333 West Wacker

    333 West Wacker

    Chicago Riverwalk

    Chicago Riverwalk

    77 West Wacker

    77 West Wacker

    Leo Burnett Building

    Leo Burnett Building

    35 East Wacker

    35 East Wacker

    Carbide and Carbon Building

    Carbide and Carbon Building

    London Guarantee Building

    London Guarantee Building

    Crain Communications Building

    Crain Communications Building

    Aon Center

    Aon Center

    Aqua Tower

    Aqua Tower

    Chicago Marine Safety Station

    Chicago Marine Safety Station

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

  • 26 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.

    25
    1
    0
    0
    0

    What our guests say

    Ardian J

    Group
    Verified booking
    3 weeks ago
    Perfect professional Cruise and workers are so nice 😊

    Cheryl W

    Solo
    Verified booking
    4 days ago
    Great and well informed tour guide. Very nice and professional.

    Maliya R

    Couple
    Verified booking
    2 weeks ago
    The boat is always a must do, and to hear awesome dad jokes

    Brenda K

    Group
    Verified booking
    Last week
    Lots of fun! Definitely worth it!

    Graham R

    Couple
    Verified booking
    Oct 2025
    Fantastic tour, beautiful tour and very informative but in a funny way. Definitely recommend
  • 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 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.

Similar experiences you'd love

Free cancellation
Couple taking a selfie at Chicago 360 Observation Deck with city skyline view.
360 Chicago Observation Deck Skip-the-Line Tickets
Landmarks
from
$30
360 Chicago Observation Deck Skip-the-Line Tickets. Rated 4.4 out of 5 from 159 ratings.From $30
Free cancellation
Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.
90-min Chicago River Architecture Cruise by Wendella
Sightseeing Cruises
$45
90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 425 ratings.From $45
View from the Skydeck at Willis Tower, Chicago, overlooking the cityscape.
Skydeck Chicago Tickets
Observation Decks
from
$42.33
Skydeck Chicago Tickets. Rated 4.7 out of 5 from 124 ratings.From $42.33
Free cancellation
big bus: chicago hop-on hop-off bus tour-1
Big Bus: Chicago Hop-on Hop-off Bus Tour
Hop-on Hop-off Tours Chicago
from
$49
Big Bus: Chicago Hop-on Hop-off Bus Tour. Rated 4.6 out of 5 from 300 ratings.From $49
Free cancellation
Family enjoying view from Chicago 360 Observation Deck with city skyline.
360 Chicago Sip & View
Observation Decks
from
$44
360 Chicago Sip & View. Rated 4.2 out of 5 from 17 ratings.From $44

How Headout makes choosing experiences effortless

We curate the best ways to experience

We research and organise all unique experiences - from tickets to tours to special combos - so you get all the choices without the clutter.

We partner with the best

Every supplier is vetted for quality, reliability, and value so you only get top rated experiences. No surprises, no disappointments.

All the best options, in one place

Each experience is thoughtfully organised to give you maximum availability, great value and an easy way to choose.

Book with complete peace of mind

Free cancellations, Flexible payments, and 24/7 support - thoughtfully designed for flexibility, assurance, and total peace of mind.

1/4

Slide 1 of 4
We curate the best ways to experience
We partner with the best
All the best options, in one place
Book with complete peace of mind
Download app section background

We've served 50 million+ guests and we are here for you

50 million+

Happy customers across 10,000+ experiences

In the media

Featured and recommended by the best brands

24 x 7 help center

Have a question? Live chat with local experts anywhere, anytime