Best Bars To Go To In Chicago

Chicago is a city that takes drinking seriously, but not itself. A great bar here can be a dim tavern with a tattered Bears flag, or a velvet-seated cocktail den where the ice costs more than your lunch. Either way, you’re welcome—as long as you don’t block the bartender’s path to the register.

Consider this a loose, unscientific map to some of Chicago’s best bars. It’s a list of places where you’ll accidentally stay for three hours and leave with a new best friend or at least a solid buzz.

Dive Bars Where You’ll Make Friends by Accident

Richard’s Bar

Richard’s Bar in Humboldt Park is loud, dim, and indifferent to your Instagram feed. It’s cash only, so bring actual money, not your tap-to-pay face. Order a beer and a shot, then settle in like you’re in your weird uncle’s living room.

Gold Star Bar

Gold Star Bar on Division Street feels like a time capsule with a cocktail shaker. The crowd mixes old-school regulars, service-industry folks, and people who claim they “don’t really go out anymore.” You’ll fit right in after the first round.

Cocktail Bars That Make You Feel Fancy Without a Dress Code

The Violet Hour

The Violet Hour hides behind an unmarked Wicker Park door, which makes you feel like you’re entering a speakeasy or an exclusive laundry room. The cocktails are serious, the rules are gentle, and the lighting makes everyone look Photoshopped. Don’t take a phone call at the bar unless you want the side-eye.

Kumiko

Kumiko in the West Loop is Japanese-inspired, precise, and dangerously easy to linger in. The drinks are balanced, the space is warm, and the bartenders treat ice like a tiny sculpture. You’ll spend too much, but you’ll feel elegant doing it.

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Beer Bars for People Who Say “I’m Just Having One”

Map Room

Map Room on Armitage is a beer lover’s library, with travel posters and a tap list that rewards curiosity. You’ll walk in planning one pint and leave debating whether a Belgian sour counts as a fruit serving. The patio is a gem when Chicago remembers what sunshine is.

Hopleaf

Hopleaf in Andersonville is famous for Belgian beers and mussels, meaning “you’ll need a nap afterward.” The bar is cozy, the fries are excellent, and the beer list is long enough to require a strategy. Bring a friend who likes to share, or pretend you will.

Music Bars Where You Can Nod Along

Green Mill

Green Mill in Uptown is a historic jazz club with curved booths, dim lights, and the ghost of Al Capone’s tab. The music is top-notch, and the vibe is “cool without trying,” which is the best kind of cool. Sit close, order something simple, and let the saxophone do the talking.

Kingston Mines

Kingston Mines runs two stages, so the blues basically never stop. It’s loud, sweaty, and unapologetically fun, like a family reunion where everyone can dance. If you leave without tapping your foot, check your pulse.

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Neighborhood Taverns That Feel Like a Warm Hug

Simon’s Tavern

Simon’s Tavern in Andersonville serves glögg in winter and feels like a Swedish grandmother’s basement, if she stocked Aquavit. It’s cozy, quirky, and perfect for a cold Tuesday.

Old Town Ale House

Old Town Ale House is a legendary corner bar with satirical paintings, strong opinions, and a jukebox that understands your mood. It’s small, so you might end up talking to strangers. That’s not a bug; it’s the feature.

Final Call

The best bar in Chicago is the one closest to your friend’s apartment when you’re too tired to be picky. But if you’re exploring, pick a neighborhood, walk into somewhere with a glowing sign, and trust your gut. Order a local beer, tip like you mean it, and let the night unfold.

Chicago bars are like the city itself: loud, warm, stubborn, and full of stories. You might come for one drink, but you’ll leave with a memory—or at least a receipt you don’t fully understand. Either way, you’ll be back.