The Best Dive Bars in Chicago

An offbeat, welcoming joint surrounded by craft breweries and fancy cocktail houses, Cole’s is a throwback that hosts revolving art exhibits, variety shows, live bands and a mentalist. It also screens films you haven’t heard of and staffs quirky DJs that spin everything from scratchy 1920s records to shoegaze singles.

Any lived-in, urban dive that pays homage to Joe Strummer, pinball and whiskey in equal measure, could be a potential classic. Delilah’s—dark, friendly and loud—is. It boasts more than 600 bourbons, ryes and Scotch whiskeys, many of them rare and top-flight, and a great jukebox packed with anthemic punk rock and swingin’ rockabilly. And though the beer list doesn’t get much glory, it’s also pretty terrific.

This Northwest side liquor store/beer bar (called a "slashie" in Chicago) is just as likely to throw a trivia night party as it is to book a live Iron Maiden tribute band. The wood-paneled walls and scruffy environs scream dive, but Fischman has its own food truck (Fischmans Wagyu Wagon) and hosts regular food-truck gatherings. It also takes craft beer very seriously, tapping 18 gems and selling even more in the store.

A hodgepodge establishment of board games, pieced together basement décor, ping pong tables and a goldfish pond-adorned backyard, Happy Village will keep any ADD drinker occupied late into the evening. Back in the day, HV's building was a tied house (a tavern subsidized by a beer company) for the 19th-century local brewery, Peter Hand, and the building still bears its seal out front. If you stick around long enough, the tamale man (Chicago's dive-to-dive tamale hawker) will stop by at least once to sell his steaming little cornmeal love letters.

The Matchbox is a Chicago institution that dates to the 1990s, well before mustachioed mixologists entered the scene. This is the kind of place where classic Collinses are still mixed with powdered sugar by a staff that truly understands that a few good Daiquiris can fix just about any bad day. Aptly named, the place is limited to less than two-dozen barstools tucked into a long, narrow room. But if the bar stools are all full—and they almost always are—there's an outdoor patio that's oddly charming despite its proximity to the highway.

Rossi’s isn’t a cocktail bar. It’s not even a beer bar. It’s a bar-bar—a perfectly sinister, open-all-day dive for those days when work simply won’t do. (It’s also technically a slashie—half bar/half liquor store—making it a true Chicago institution.) Located smack-dab in the middle of downtown, it’s close enough to the edges of The Loop, River North and Michigan Avenue to serve as a catchall rendezbooze point. Rossi’s is devoid of sunlight and always has at least a strand of Christmas lights thrown up in a corner, underscoring the theory that once inside, the world outside might as well come to a standstill.

The neighborhood’s Swedish history lives on in this worn-and-warm tavern, which dedicates one whole wall to a deer-hunting mural featuring regulars from years past. There are also goblets of seasonal homemade glögg (mulled wine), Viking tchotchkes and an iconic neon sign out front featuring a fish holding a martini glass. (Pickled herring. Get it?)

The sister bar to Wicker Park’s Rainbo Club, Skylark is by far the coolest bar in Pilsen. It’s a timeless Chicago haunt: long wooden bar, cracked vinyl booths, faded linoleum, minimal lighting and questionable bathrooms. It all lends just enough charm to lure its patrons to stay longer than planned, aided by good music and solid crowd. There’s a better-than-average bar menu, too.