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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.
Official Chicago Architecture Cruise by First Lady
Sightseeing Cruises
$57
Official Chicago Architecture Cruise by First Lady. Rated 4.9 out of 5 from 247 ratings.From $57
Chicago River cruise boat with city skyline in the background.
Chicago River & Lake Sightseeing Cruise by First Lady
Sightseeing Cruises
from
$46
Chicago River & Lake Sightseeing Cruise by First Lady. Rated 4.8 out of 5 from 5 ratings.From $46
Free cancellation
Tour boat on Chicago River with city skyline in background.
Chicago River Architecture Cruise
Sightseeing Cruises
from
$28
Chicago River Architecture Cruise. Rated 4.8 out of 5 from 369 ratings.From $28
Crowd on Chicago Haunted River "Creepy Cruise" by First Lady under moonlit skyline.
Chicago Haunted River "Creepy Cruise" by First Lady
Sightseeing Cruises
from
$46
Chicago Haunted River "Creepy Cruise" by First Lady. Rated 4.5 out of 5 from 2 ratings.From $46
Free cancellation
Tour boat on Chicago River with city skyscrapers in the background.
Lake Michigan Cruise
Sightseeing Cruises
from
$32.50
Lake Michigan Cruise. Rated 4.8 out of 5 from 191 ratings.From $32.50
Free cancellation
Guided group walking under Calder's Flamingo sculpture in Chicago.
Architecture Center Admission with Must-See Chicago Walking Tour
Museums
$35
Architecture Center Admission with Must-See Chicago Walking Tour. Rated 0 out of 5 from 0 ratings.From $35
Selling out fast
Skyscrapers at 111 E. Wacker Dr. in Chicago with clear blue sky.
Chicago Architecture Center Admission With Walk Through Time Tour
Museums
$35
Chicago Architecture Center Admission With Walk Through Time Tour. Rated 0 out of 5 from 0 ratings.From $35
Chicago Theatre marquee lit up at night with nearby subway entrance.
The Chicago Theatre Tour Experience
Guided Tours
from
$28.12
The Chicago Theatre Tour Experience. Rated 0 out of 5 from 0 ratings.From $28.12

Browse by themes

Museums in Chicago
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Observation Decks in Chicago
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Hop-on Hop-off Tours Chicago
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Airport Transfers in Chicago
Public Transport Tickets in Chicago
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Sightseeing Cruises in Chicago
Dinner Cruises in Chicago
Lunch Cruises in Chicago
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Combos Tickets in Chicago
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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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