Processing your payment

Headout logo. Link to home.
Help

Top experiences in Chicago

41 experiences

Free cancellation
Chicago River cruise boat passing under a bridge with city skyline.
Sightseeing Cruises
45-min Chicago River Architecture Cruise by Wendella
from
$28
45-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 547 ratings.From $28
Free cancellation
Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.
Sightseeing Cruises
90-min Chicago River Architecture Cruise by Wendella
$45
90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 346 ratings.From $45
Free cancellation
Guests dining on Odyssey Lake Michigan Dinner Cruise at sunset.
Dinner Cruises
Odyssey Lake Michigan Dinner Cruise
from
$136.68
Odyssey Lake Michigan Dinner Cruise. Rated 5 out of 5 from 1 ratings.From $136.68
Free cancellation
Odyssey Chicago River boat cruising on the Chicago River with city skyline.
Sightseeing Cruises
Odyssey Chicago River Architecture Dinner Cruise
from
$147.62
Odyssey Chicago River Architecture Dinner Cruise. Rated 4.7 out of 5 from 18 ratings.From $147.62
Cruise boat on Chicago River passing under Clark Street Bridge.
Sightseeing Cruises
Official Chicago Architecture Cruise by First Lady
$57
Official Chicago Architecture Cruise by First Lady. Rated 4.9 out of 5 from 48 ratings.From $57
View from the Skydeck at Willis Tower, Chicago, overlooking the cityscape.
Observation Decks
Skydeck Chicago Tickets
from
$42.33
Skydeck Chicago Tickets. Rated 4.7 out of 5 from 111 ratings.From $42.33
Free cancellation
Couple taking a selfie at Chicago 360 Observation Deck with city skyline view.
Landmarks
360 Chicago Observation Deck Skip-the-Line Tickets
from
$30
360 Chicago Observation Deck Skip-the-Line Tickets. Rated 4.3 out of 5 from 152 ratings.From $30
Free cancellation
Guests enjoying drinks on a Lake Michigan dinner cruise with Chicago skyline in the background.
Dinner Cruises
Lake Michigan Dinner Cruise
from
$121.65
Lake Michigan Dinner Cruise. Rated 0 out of 5 from 0 ratings.From $121.65
Free cancellation
big bus: chicago hop-on hop-off bus tour-1
Hop-on Hop-off Tours Chicago
Big Bus: Chicago Hop-on Hop-off Bus Tour
from
$45
Big Bus: Chicago Hop-on Hop-off Bus Tour. Rated 4.6 out of 5 from 298 ratings.From $45
Free cancellation
Cruise boat on Lake Michigan with Chicago skyline at sunset.
Sightseeing Cruises
90-min Scenic Sunset Lake Michigan Cruise by Wendella
$45
90-min Scenic Sunset Lake Michigan Cruise by Wendella. Rated 4.9 out of 5 from 18 ratings.From $45
Free cancellation
Chicago River architecture cruise boat passing under a lift bridge with city skyscrapers in the background.
Sightseeing Cruises
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella
$45
90-min Chicago River and Lake Michigan Architecture Cruise by Wendella. Rated 4.7 out of 5 from 56 ratings.From $45
Free cancellation
Big Bus Chicago tour and Chicago 360 observation deck view.
Combo
Combo (Save 10%): Chicago Hop-on Hop-off Bus Tour + 360 Chicago Observation Deck Skip-the-Line Tickets
from $75
$67.50
10% off
Combo (Save 10%): Chicago Hop-on Hop-off Bus Tour + 360 Chicago Observation Deck Skip-the-Line Tickets. Rated 4.5 out of 5 from 449 ratings.From $67.50
Show more

Browse by themes

Museums in Chicago
Chicago City Cards
Landmarks in Chicago
Observation Decks in Chicago
View all Chicago Attractions
Guided Tours in Chicago
Hop-on Hop-off Tours Chicago
View all Chicago Tours
Airport Transfers in Chicago
Public Transport Tickets in Chicago
Shared Airport Transfers
View all Transportation in Chicago
Sightseeing Cruises in Chicago
Dinner Cruises in Chicago
View all Cruises in Chicago
Combos Tickets in Chicago
View all Chicago Specials

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 49 million+ guests and we are here for you

49 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