Compared to other sleepless cities, like Las Vegas and New York, Chicago may not be the most obvious destination for late-night revelry, but the Second City is really second to none when it comes to past-your-bedtime fun. During the day, this mighty metropolis is well known for its world-class museums, festivals, shopping, parks, and restaurants. Come sunset, the city continues to awe. Under the twinkling glow of one of the country’s best skylines, you’ll find all manner of activities and attractions worth staying up for, from bougie billiards and after-hours museums to sleight of hand with a side of goat cheese. The all-night entertainment isn’t confined to summer, either. Just because the winter weather outside is often frightful doesn’t make nightlife in Chicago any less action-packed—plus there’s the added bonus of “after dark” in winter meaning “any time after, like 4:30 pm.” Which means more time to partake in any of these 12 things to do in Chicago after dark.
Game Room | Photo by Clayton Hauck
Pair billiards with fried chicken sandwiches
Loop
Bocce gets a serious glow up at Game Room, a retro-chic billiards bar nestled inside the Chicago Athletic Association hotel downtown. A far cry from the endearingly dusty dive bar stereotypes, this modestly dubbed bar is a sprawling adult playground filled with classic games like bocce, chess, shuffleboard, and checkers—all served up with food and drink menus that go far beyond the call of checkers duty. Owned by the same folks behind some of Chicago’s most beloved late-night haunts, like Parson’s Chicken & Fish and Lonesome Rose, you’ll find crowd-pleasing snacks like Parson’s fried chicken sandwiches, Lonesome Rose beef tacos, whitefish patty melts, and foot-long hot dogs, plus frozen Malort cocktails (if you know you know) and other classic-inspired tipples. It’s game on until 11 pm Monday – Thursday, and until 2 am Friday – Saturday.
See a free late-night show
Ukrainian Village
Late-night live music is a rite of passage in Chicago, and while there are always new venues popping up all over town, there’s always something nostalgic about revisiting an old haunt. For the most heartwarming, intoxicating blast from the past, head to the Empty Bottle, a Ukrainian Village institution that’s been pumping out live shows and dirt-cheap beer since 1992.
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