The Best After-Hours Bars in Chicago

Founded as a tribute to its owner’s boyhood summers in Burlington, Wisconsin, this rock 'n' roll bar is dark, loud and low-key. Vintage church pews line the walls, a cluster of bare bulbs barely illuminate the bar and a retro wall decal of a woodsy, autumnal scene sets the Midwestern mood. In the back room, bands play for the price of a few pints, most of which are local or regional (both the bands and the beers). If you must, there’s a full stock of liquor, but anything other than shots or a whiskey and ginger is likely to raise an eyebrow. Unlike most of Logan Square’s bars, The Burlington is refreshingly ...

Back in the mid-aughts, when the Continental opened its doors on an isolated industrial strip with views of a train yard, foot traffic came from the only place around: the Superior Street band rehearsal warehouse down the block. Little has changed since. The bar, infamously dubbed “Mistakes” by the local hipsterati, still draws a rock ‘n’ roll crowd content to chug beers 'til the wee hours, and the jukebox still spins an eclectic mix of cult-classic rock.

Long, narrow and always packed, Estelle’s is an after-hours go-to thanks to its prime location in the heart of Wicker Park and Bucktown’s Six Corners and its 4 a.m. liquor license (5 a.m. on Saturdays). With art deco décor illuminated by a sinister red glow, the place has a sultry, vintage vibe that lends itself well to late-night conversations and canoodling. Don’t let the early evening quietude fool you: Estelle’s doesn’t really wake up 'til after midnight.

In a city of institutions, the Green Mill is exemplary for its ties to both Prohibition-era speakeasies and Chicago’s legendary jazz scene. Established in the early 1900s, the North Side cocktail lounge was a go-to for Al Capone and his gang, who allegedly avoided run-ins with the law by sneaking out via the back bar’s hidden tunnels. These days, it’s best known for nightly live jazz and the renowned Uptown Poetry Slam, which has been hosted here since the 1980s.

We like to think of this watering hole as everything to everyone. It’s a bar; it’s a lounge; it’s a low-key place to have a Martini; it’s a sweaty late-night spot to get your dance on. Really, it all depends on the day of the week, who’s DJing and how late you’re willing to stay out (you’re welcome until 4 a.m. weeknights and 5 a.m. Saturday nights).

During the week, the Rainbo effortlessly defends its reputation as a timeless, maroon-vinyl-boothed tribute to 1980s post-punk cooldom, luring generations of hipsters who know a legit dive when they smell one. Sadly, come Saturday nights, it’s a victim of its own geography: an untouchable icon whose Damen & Division address was once dodgy, and is now unfashionably yuppie. Still, it’s worth stopping in for a round, even if the cheap beer and cheaper liquor are more means to an end than anything else.