Capture a magical moment
Chicago Magic Lounge
Magic shows aren’t just for kids anymore, especially when they’re presented with a side of booze in a lux space. There are various spots to catch a magic show in the city, but the Chicago Magic Lounge whisks you away the moment you enter through the faux-laundromat door. Have a cocktail and share a small bite or two as you settle in for an evening of illusion and mystery -- the lounge is open until 2am, Fridays and Saturdays.
Visit a (quality) sex shop
Whether you’re in the market for a new toy, want to stock up on lube or simply study up on the latest kinks, a stroll around the sex shop with an open-minded friend makes for a night full of laughs and maybe even a touch of pleasure. The Lincoln Avenue location of The Pleasure Chest is open till midnight and even offers workshops on topics like sex and disability, squirting, and pleasing the penis, while Early to Bed in Andersonville was founded with the mission of providing a safe space for folks of all genders.
Eat, drink, and sing in Chinatown
Chinatown is one neighborhood that never sleeps. Chi Cafe, for instance, is open until 4am during the week and 24 hours on Fridays and Saturdays. Even in the winter, you’ll spot people having bubble tea or ice cream, and if you’re not in the mood for food there’s always karaoke. Spots like Sakura Karaoke Bar and Zero Degree Karaoke Bar and Club are open until 2am or 3am.
Watch a midnight movie
Music Box Theatre
There are times for matinees, times for movies in the park and times for cult classics when the clock strikes 12. Around since 1929, the Music Box is a Chicago institution that hosts all types of events, including midnight showings of classics like The Room -- bring your own spoons! -- The Rocky Horror Picture Show, and other rotating features.