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Chicago Dates That Scream Halloween

Posted on October 24, 2023   |   Updated on September 30, 2025
Sidney Madden

Sidney Madden

Haunted Seadog River Cruise

Haunted river cruise. (Courtesy of City Cruises Chicago)

Hey Chicago rounded up some of our favorite date ideas around the city to get you into the Halloween spirit.

For Pirates at Heart: Haunted River Tour

Sail the haunted waters of the Chicago River to learn about the city’s spooky past and historic architecture. BYOB! Dogs are also welcome.

Catch scary movies like “Nope” and “The Exorcist” at the movie venue. “Coraline” is as scary as it gets for this newsletter editor …

The insect and taxidermy museum has all types of critters to learn about — including scorpions you can help preserve.

For Costume Enthusiasts: Bronzeville Contest

Dress as your favorite Chicago historical figure and win a 1-year membership to Bronzeville Winery’s wine club. Hop on board for historian Shermann “Dilla” Thomas’ two-hour bus tour.

Two clowns in the Hot Clown show

Hot Clown Company show. (Courtesy of Hot Clown Company)

Don’t let the clown noses and fake blood fool you: This Halloween–themed variety show is the raunchiest date on the list.

See the graves of former Chicago mayors, Olympian Jesse Owens, and civil rights activist Ida B. Wells at the 183-acre cemetery.

For ‘Chucky’ Fans: Old Town Haunted Doll Hunt

Search for 13 dolls at the Chicago History Museum by solving riddles.

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