Kingston Mines offers free or discounted cover to students, members of the military and seniors. Green Mill is perfect for those who appreciate live jazz in a speakeasy atmosphere while Rosa's Lounge lets you enjoy live blues without the unnecessary pretentiousness of a club-like atmosphere. Many clubs offer nightly performances 365 days a year. ![]() Luckily one doesn’t need to wait for the free festivals to enjoy live music in Chicago. King, Bo Diddley, Buddy Guy and Koko Taylor while the Jazz Fest shows off Chicago's vast jazz talent alongside national and international artists to encourage and educate a jazz audience of all ages. Past performers of the Blues Fest include Ray Charles, B.B. The city’s annual Chicago Blues Fest and Chicago Jazz Fest are popular free events that take place during the summer. If you’ve got room for one more, sip some whiskey at Longman & Eagle and then stumble upstairs, where the hipster tavern doubles as an inn with a few beautifully designed rooms.Music lovers crowd Chicago’s blues and jazz clubs where legendary figures as Von Freeman, Franz Jackson and Eddy Clearwater have played. For an alluring speakeasy vibe, descend into Golden Teardrops, a nondescript basement bar underneath Lonesome Rose that’s so dark it feels like a haunted house that just happens to make a killer nightcap. ![]() The neighborhood has its fair share of timeworn dives too, like Whirlaway Lounge and Bob Inn, while The Owl and Cole’s Bar are the kinds of dives with dance tunes. The same folks behind the latter put the spotlight on wine at artsy, wood-filled bar Outside Voices, while Union is an impressive beer bar with an equally stunning food menu from the meaty minds behind nearby Lardon. The northwest side neighborhood, conveniently accessed right off the Blue Line (so you can save money on regrettably tipsy Uber expenses), Logan Square is home to Instagrammable cocktail haunts like tropical Estereo, swanky Billy Sunday, tavern-inspired Spilt Milk, and The Heavy Feather, a retro-glam fern-filled bar above dance club Slippery Slope. Practically all Chicago neighborhoods have their share of CTA-worthy bars, pubs, taverns, and dives, but perhaps nowhere is the drinking scene more dynamic-and worthy of a bar crawl-than Logan Square. 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. The all-night entertainment isn’t confined to summer, either. ![]() 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. During the day, this mighty metropolis is well known for its world-class museums, festivals, shopping, parks, and restaurants. 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.
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