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Friends and Groups in Chicago

Browse through our selection of interesting experiences in Chicago, carefully curated for friends and groups of all sizes.
Friends walking together on a sunny day near a safari vehicle, enjoying a group adventure.

Top things to do

Wendella Cruises Chicago
Wendella Cruises Chicago
from $28
Hurricane Harbor Chicago
Hurricane Harbor Chicago
from $36.40

Top experiences in Chicago

Free cancellation
Fireworks over Chicago River with boats during dinner cruise.
Chicago Fireworks Dinner Cruises
Sightseeing Cruises
from
$112.10
Chicago Fireworks Dinner Cruises. Rated 3.3 out of 5 from 12 ratings.From $112.10
Free cancellation
Fireworks over Chicago River with boats during dinner cruise.
Chicago Fireworks Cruise
Sightseeing Cruises
from
$54.76
Chicago Fireworks Cruise. Rated 3.8 out of 5 from 17 ratings.From $54.76
Visitors on a water slide at Hurricane Harbor Chicago with a lifeguard nearby.
Hurricane Harbor Chicago One Day Ticket
Water Parks
$36.40
Hurricane Harbor Chicago One Day Ticket. Rated 0 out of 5 from 0 ratings.From $36.40

Browse by themes

Museums in Chicago
Theme Parks in Chicago
Water Park Tickets 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.

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

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