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Chicago for families

Discover a world of family adventure in Chicago! From thrilling theme parks to delightful zoo and aquarium visits, we have curated the best options for the perfect family getaway.
Family enjoying bubble play at an amusement park with a Ferris wheel in the background.

Top things to do

360 Chicago
360 Chicago
from $27
Willis Tower Skydeck Tickets
Willis Tower Skydeck Tickets
from $42.33
Six Flags: Great America
Six Flags: Great America
from $46.80

Top experiences in Chicago

Free cancellation
Guests dining on Odyssey Lake Michigan Dinner Cruise at sunset.
Odyssey Lake Michigan Dinner Cruise
Dinner Cruises
from
$132.58
Odyssey Lake Michigan Dinner Cruise. Rated 4.7 out of 5 from 93 ratings.From $132.58
Free cancellation
Chicago River with tour boats and bridges in downtown Chicago.
Sea Dog Cruise on Lake Michigan
Dinner Cruises
from
$35.72
Sea Dog Cruise on Lake Michigan. Rated 5 out of 5 from 4 ratings.From $35.72
View from the Skydeck at Willis Tower, Chicago, overlooking the cityscape.
Skydeck Chicago Tickets
Observation Decks
from
$42.33
Skydeck Chicago Tickets. Rated 4.8 out of 5 from 128 ratings.From $42.33
Riders upside down on Maxx Force roller coaster at Six Flags Great America.
Six Flags Great America One Day Tickets
Theme Parks
from
$46.80
Six Flags Great America One Day Tickets. Rated 4.8 out of 5 from 6 ratings.From $46.80

Browse by themes

Museums in Chicago
Theme Parks 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
Lunch Cruises in Chicago
View all Cruises in Chicago
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 51 million+ guests and we are here for you

51 million+

Happy customers across 10,000+ experiences

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