Top experiences in Chicago

41 experiences

Moored tour boats on the Chicago River at sunrise with city skyline.

Sightseeing Cruises

Chicago Architecture Evening Cruise by Shoreline

Unavailable

Chicago Architecture Evening Cruise by Shoreline. Rated 5 out of 5 from 21 ratings.

Cruise boat on Lake Michigan with Chicago skyline in the background.

Sightseeing Cruises

45-Min Lake Michigan Tour by Shoreline

Unavailable

45-Min Lake Michigan Tour by Shoreline. Rated 4.2 out of 5 from 11 ratings.

Free cancellation

Guest viewing Chicago skyline from lakefront during Skydeck and Architecture Cruise tour.

Guided Tours

Chicago Skydeck & Architecture Cruise with Small Group Guided Tour

Unavailable

Chicago Skydeck & Architecture Cruise with Small Group Guided Tour. Rated 5 out of 5 from 1 ratings.

Landmarks

Adler Planetarium

Unavailable

Adler Planetarium. Rated 0 out of 5 from 0 ratings.

Art Institute of Chicago entrance with iconic lion statue and city skyline.

Art Institute of Chicago Fast Pass Tickets

Unavailable

Art Institute of Chicago Fast Pass Tickets. Rated 0 out of 5 from 0 ratings.

Field Museum of Natural History entrance with columns and banners in Chicago.

Museums

Field Museum of Natural History Tickets

Unavailable

Field Museum of Natural History Tickets. Rated 0 out of 5 from 0 ratings.

Cirque du Soleil 'Twas The Night Before poster with excited child and festive elements.

Circus

Cirque du Soleil 'Twas the Night Before: Chicago

Unavailable

Cirque du Soleil 'Twas the Night Before: Chicago. Rated 0 out of 5 from 0 ratings.

Field Museum interior with dinosaur skeleton and elephant exhibit, Chicago.

Museums

Field Museum of Natural History

Unavailable

Field Museum of Natural History. Rated 0 out of 5 from 0 ratings.

Musicals

Million Dollar Quartet

Unavailable

Million Dollar Quartet. Rated 0 out of 5 from 0 ratings.

Silhouettes of jazz musicians playing saxophone, trombone, and trumpet against a city skyline.

Private Tours

Jazz & Blues Tour

Unavailable

Jazz & Blues Tour. Rated 0 out of 5 from 0 ratings.

Musicals

Blue Man Group

Unavailable

Blue Man Group. Rated 0 out of 5 from 0 ratings.

Sky Deck Chicago

Unavailable

Sky Deck Chicago. Rated 0 out of 5 from 0 ratings.

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Museums in Chicago

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Landmarks 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

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Top experiences in Chicago

Browse by themes

How Headout makes choosing experiences effortless

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

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