City Cast Chicago logo

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.

Share article

Hey Chicago

Stay connected to City Cast Chicago and get ready to join the local conversation.

Can't subscribe? Turn off your ad blocker and try again.

The latest in Chicago

Neighborhood GuidesSeptember 16

7 New Spots to Dine and Drink

Seven recently opened bars and Restaurants in Chicago

Two people at a table holding up their drinks. On the table there's a martini with olives.
Chicago, ExplainedSeptember 15

The Latest Candidates Running For Mayor

Mayor Brandon Johnson officially launched his reelection campaign, joining a race that includes roughly a dozen other challengers.

A composite photo of three people. On the left is a man in glasses and a dark suit. In the middle is a man in a blue suit, on the right is a woman wearing blue feathers and with white hair
Chicago, ExplainedSeptember 11

Take This Week's Chicago News Trivia Quiz

How closely were you paying attention to this week's current events in Chicago? Test yourself in our weekly trivia quiz.

A large brick building with glass roof and intricate metal on the corners
Keep It LocalSeptember 10

Sheep Cult Comics Celebrates Local Chicago Comic Artists

Stepping into Sheep Cult Comics, you’re surrounded by whimsical, winding caverns of cloud-like shelves, presided over by sculpted sheep h...

A large entrance in a store in the shape of a sheep. There are books along both sides of it
Keep It LocalSeptember 10

Your Guide To Chicago’s Comic Book Stores

I’ve compiled a list of stores where you can find the newest graphic novels, affordable used comics, or even your next favorite board gam...

Comics on display in what looks to be a multicolored customized bookshelf
Chicago, ExplainedSeptember 8

Mayor Brandon Johnson Answers YOUR Tough Questions

Mayor Brandon Johnson told City Cast Chicago he’ll announce whether he’s running again Sept. 13. And that’s not all he said. We sat down...

Two men sitting across from each other at a table looking at the camera. The man on the left has his arms crossed and is holding a piece of paper. The man on the right has a suit on and is showing a peace sign
Keep It LocalSeptember 3

Your Guide To Karaoke Bars in Chicago

Whether your perfect karaoke night involves performing to an entire bar or renting a room for a more intimate experience, you’ve got opti...

A woman singing into a mic. A man is holding up what looks to be a tv screen
Keep It LocalSeptember 3

The Art of Karaoke

Karaoke is pretty serious business, and I want to make sure you know what you’re getting yourself into.

A woman singing into a mic with her finger pointed up. There's a man behind her holding a screen