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United StatesChicago, United States

Chicago for history geeks

Immerse yourself in Chicago’s heritage with our selection of historical experiences and guided tours. Perfect for all you history enthusiasts.
Ancient Mayan artifacts in a museum exhibit, ideal for history buffs.

Top things to do

First Lady Cruises Chicago
First Lady Cruises Chicago
from $28
Chicago Architecture Center
Chicago Architecture Center
from $15

Top experiences in Chicago

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 47 ratings.From $57
Couple taking a selfie in a gallery at The Art Institute of Chicago.
Museums
The Art Institute of Chicago Tickets
$40
The Art Institute of Chicago Tickets. Rated 0 out of 5 from 0 ratings.From $40
Free cancellation
Guided group walking under Calder's Flamingo sculpture in Chicago.
Museums
Architecture Center Admission with Must-See Chicago Walking Tour
$35
Architecture Center Admission with Must-See Chicago Walking Tour. Rated 0 out of 5 from 0 ratings.From $35
Free cancellation
Skyscrapers at 111 E. Wacker Dr. in Chicago with clear blue sky.
Museums
Chicago Architecture Center Admission With Walk Through Time Tour
$35
Chicago Architecture Center Admission With Walk Through Time Tour. Rated 0 out of 5 from 0 ratings.From $35

Browse by themes

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

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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.

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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

We've served 48 million+ guests and we are here for you

48 million+

Happy customers across 10,000+ experiences

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