Step into the Dark

It might not have the harrowing history of Stephen King's Overlook Hotel, but the Chicago Athletic Association certainly has an eerie, antiquated atmosphere—which makes it the perfect place for a creepy Halloween party. This year, guests will enjoy palm and tarot readings on the hotel's first floor, before moving up to the Game Room for appearances by artists and musicians. The evening ends in the Stagg Court, where throwback country singer Nikki Lane will perform. Attendees are encouraged to arrive in costume (there's even a mood board to guide your attire).