11 Best Bars in Wicker Park, Chicago

This place may have toys and knickknacks around the bar (including a case of macabre baby-doll heads), but when it comes to booking rock, punk, and jazz bands from the indie scene, it's a serious place with no pretensions. Grab some grub next door at Pizza Friendly Pizza before the show—the thick Sicilian-style squares, created in collaboration with fine dining vet Noah Sandoval, are among the best pizza bets in the whole city.

The Hideout, which is literally hidden away in a North Side industrial zone, has managed to make country music hip in Chicago. Players on the city's alternative country scene have adopted the friendly hole-in-the-wall, and legendary local acts like Wilco and Andrew Bird have been known to use the crowd here as a sounding board for new material. Late-night DJ sets, stand-up, and even the odd square dance round out the entertainment offerings.

In West Town near Wicker Park, the Matchbox isn't much bigger than a you-know-what, but the hodgepodge of regulars doesn't seem to mind. In fact, many claim it's the dark, cramped quarters (we're talking three feet wide at its narrowest) that keep them coming back. A heated front patio comes in handy when you need to reclaim a little personal space. You're practically required to try the signature drink, a margarita.

Lovers of vintage bar rooms will be in heaven at this veritable 1950s-era time capsule on Division Street. After shuttering in 1975, it was left undisturbed until 2015, when a local hospitality group dusted off the warm wooden interior and reopened the doors. Today there’s an emphasis on nautical quaffs like grog and navy strength gin. The Sunday and Monday oyster and martini happy hour is a favorite with locals.

Two of America’s favorite pastimes—drinking and playing classic arcade games—come together here. More is more is the governing M.O.: there are over three dozen arcade games to choose from, along with Skee-Ball, pinball machines, and around two-dozen beers on draft. There are also locations in Logan Square and the West Loop. 

Done up in pretty Prussian blue with warm walnut accents, this wine bar/bottle shop channels calm vibes—and if you're still feeling keyed up, a pour or two from the Eurocentric wine list should do the job. Standard wine bar fare like cheese and charcuterie plus a few Spanish-inspired pintxos make up the small food menu. 

Chicago hipsters and indie rockers have made Rainbo Club their unofficial meeting place. Apart from the working photo booth wedged into a corner, the stripped-down hangout is pretty barren, but drinks are dirt cheap and the crowd is loyal.

Grab a biscuit and a tang (that is, a shuffleboard disc and cue) and embark on a vacation within a vacation at this Brooklyn import, featuring 11 shuffleboard courts (one of them up on a seasonal rooftop deck) that channel a retro cruise ship, as well as a rotating lineup of food trucks and tropical cocktails. Courts are first come, first served; to minimize the wait, try turning up at opening time (that's 5 pm on weekdays, and noon on weekends).   

This Ukrainian Village bar’s roots as a nightspot for local Polish immigrants can still be felt in its warm wood accents and retro backbar. Classic cocktails are the drink of choice; they pair perfectly with the warmth of the back patio’s brick fireplace.

Check the letter board over the front door of this Wicker Park storefront for a list of the rising indie rock and hip-hop acts playing there soon, often on their first Chicago gigs. Chances are good they'll be playing a larger venue the next time through. Locals also come for the popular Thursday reggae nights and regular open-mic events.

The Violet Hour channels a Prohibition-era speakeasy—an unmarked door in the mural-covered facade leads to a mysterious, curtained hallway. Inside, twinkling crystal chandeliers cast a glow on cornflower-blue walls, and extremely high-backed blue leather chairs encourage intimate conversations. Add to that pricey but flawlessly executed cocktails and a small menu of refined snacks, and it's our idea of nightlife heaven.