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Hepcats, artists, and yuppies converge on the famed six corners of North, Milwaukee, and Damen avenues, where the cast of Real World Chicago once resided. Previously scruffy and edgy, the area is now dotted with pricey, upscale bars, though the occasional honky-tonk still survives. Logan Square, in particular, has seen an explosion of new nightlife venues in recent years. Those looking for a dance party tend to head to the Debonair Social Club or Slippery Slope, while cocktail connoisseurs brave the wait at the Violet Hour.
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.
Just a stone's throw from Second City, Old Town Ale House has attracted a diverse cast of characters since it opened in 1958, including comedy legends John Belushi and Bill Murray. With eclectic artwork and a mural of bar denizens painted in the 70s, it's a dingy neighborhood bar unlike any other in the city—perhaps the country. Esteemed film critic Roger Ebert called it "the best bar in the world."
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.
This breezy, seasonal, casual bar and grill puts you so close to Lake Michigan that you might consider wearing a swimsuit. Perched atop the North Avenue Beach Boathouse, Castaways creates the perfect setup for lazy summertime sipping.
The old-school taverns tucked at random along Bucktown's residential streets---many distinguished by a vintage Old Style beer sign---are a major contributor to the neighborhood's character, and this one (the latest iteration of a series of bars that have existed on this site since the 1950s) is a prime example. Come for the ice-cold beer, the easygoing dive vibe, and the jukebox tunes.
A rare dive bar amid Lincoln Park's tonier establishments, Delilah's is dark and a bit grungy. But the bar has a friendly, unpretentious vibe and a standout whiskey selection (more than 800 types are on offer). DJs spin punk, metal, and rockabilly.
Mexican spirits like mezcal, sotol, and raicilla are the focus at petite Estereo, which has an unusual triangular shape due to its position on an angled corner lot. When the garage-style windows that surround the room are rolled up and the vintage Latin tunes are pumping, you’d be forgiven for thinking you’d been transported to a city much nearer to the equator.
Come summer, Ludlow gets top marks for its spacious back patio, and when the weather goes south, it's hard to fathom a cozier spot than one of the high-backed stools that flank the handsome vintage bar. Whatever the season, the drinks here are stiff, and the smash burgers hit the spot. Check the website for the monthly roster of quirky events, like musical bingo nights and tarot readings.
The Map Room might help you find your way around Chicago, if not the world. Guidebooks decorate the walls of this self-described "travelers' tavern," and the craft beers represent much of the globe. This is a favorite gathering spot for soccer fans, so expect it to be roaring during World Cup season.
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.
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.
