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.
For Cinephiles: Rooftop Cinema Club in Fulton Market
Catch scary movies like “Nope” and “The Exorcist” at the movie venue. “Coraline” is as scary as it gets for this newsletter editor …
For Bug Lovers: The Insect Asylum in Avondale
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.

Hot Clown Company show. (Courtesy of Hot Clown Company)
For Oddballs: Hot Clown Horror Show in Uptown
Don’t let the clown noses and fake blood fool you: This Halloween–themed variety show is the raunchiest date on the list.
For Historians: Grand Crossing Oak Woods Cemetery
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.