Cheers! Grab a Drink at One of the Best Bars in Chicago

Chicago is a city that knows how to enjoy a drink. Even prohibition couldn't do much to put a damper on the city's bar scene—it was a haven for bootleggers and speakeasies in the Roaring 20s—and that tradition carries on to this day. Of course, today you don't need a secret knock to get into the best bars in Chicago, you just need to show up thirsty.

Come One, Come All

Tucked away in an unassuming corner of Lincoln Park, Delilah’s is a melting pot in the best way. Here you'll find hipsters rubbing shoulders with metal heads and working professionals alongside tattooed punk rockers. It all adds up to a fun, anything-goes vibe, with DJs spinning music that ranges from hard rock and reggae to traditional country and R&B, depending on the night. It also helps that Delilah's has one of the best whiskey selections in Chicago, and they're no slouch in the craft beer department, either.

A Gem of a Gin Joint

Scofflaw offers cocktails to suit any palette and budget, but this Logan Square gem is, at its heart, a gin joint. You're not likely to find a better selection of this often overlooked spirit at any other bar in Chicago. Scofflaw's brick and wood interior gives it a cozy Victorian atmosphere, and if you start to feel a bit hungry, they serve up some tasty small plates that are surprisingly filling.

Savor the View and Save a Little Money

Plymouth Restaurant & Rooftop Bar may be one of the best rooftop bars in Chicago, but it's special for another reason: Unlike many of Chi-Town's upscale rooftop lounges, Plymouth is almost shockingly easy on your wallet. The relaxed atmosphere and affordable specials, like cheap martinis Monday through Friday, make it a great casual hangout. Plymouth also sweetens the deal with a great view and tasty pub grub. Plus, thanks to outdoor heating and removable enclosures, it's open year-round in all weather.

Dive Into a Classic Dive Bar

Let's not beat around the bush—if you're looking for a dive bar, this is your place. You could call Richard's Bar on Milwaukee Ave. an old man's bar, and there's not a thing in the world wrong with that. The atmosphere is dingy, the beer is cheap, the jukebox is loaded with Rat Pack classics and the bartenders do not suffer fools. The clientele ranges from local old-timers to college students and out-of-towners looking for a home away from home.

Craft Beers and Community Cheers

A mainstay of Chicago's South Side, Maria's Packaged Goods & Community Bar is the kind of bar you'll want to revisit every time you come to Chicago. It stocks 200 to 300 selections of American craft beer at the bar—plus many more in the bottle shop, where you can buy it to go. They also serve terrific Korean-Polish fusion fare from the adjacent Kimski Kitchen. The crowd is famously warm and friendly, and the beautifully designed building is a work of art unto itself.

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