One thing we've always appreciated about the city of Chicago is how acceptable it is to be drunk in public at all hours of the day. Grocery store chains legitimately offer wine bars and outfit their carts with fucking glass holders so you can get wasted with ease while you buy cereal. This is Chicago and we have a God-given right to drink wherever and whenever we please.
Day drinking isn't just tolerated, it's downright encouraged—just remember the unspoken rules: no puking, no punching, no unsolicited ass grabs. Screaming incoherently is fine so long as it's about the weather, the Cubs, or Rahm Emanuel. But for the last time, no, we don't want a shot of Malort because we are human beings and not sentient trash disposals.
This prominent drinking culture means there are thousands of great places to get drunk in the city, so this is not an exhaustive list by any means. These bars are for the most part years-old Chicago staples that feature pool tables, jukeboxes, big booths, and occasionally craft cocktails. These are the bars to go to if you want to have one of those intense 2 AM heart-to-hearts with a stranger.
Basically everyone can agree that "lesbian karaoke dive bar" is by far the most beautiful phrase in the English language. In addition to being the physical embodiment of these four words, the drinks at Spyner's are strong, the bartenders are sassy, the regulars are kooky and the line for karaoke is never too long. The negative Yelp reviews are often straight, white dudes complaining about how lesbians get better service which, in our opinion, is always the mark of a good bar.
The Violet Hour
This place is classy as fuck. There's no sign, because of course there isn't, and the entrance is a hidden door on the ever-changing mural adorning the wooden building across from Big Star. Inside it's all velvet curtains, $13 craft cocktails that taste otherworldly, and delicious appetizers you can share with your table of fancy friends. The "house rules" card they present you with is just pretentious enough to make you feel superior to everyone in the line of shivering, well-dressed fools waiting to get in. You made it. You're here. It's happening.
Craft beer bar in the front, bump n' grind dance party in the back. The front bar's got a pool table, 16 different beers on tap, and a jukebox full of live-recorded rock songs, but the back bar is a world of its own. Expect steamy, sensual grinding to classic R&B hits, and plenty of sweaty singles to rub up against. We don't want to put too fine a point on it, but if it's been awhile since you got laid, this is gonna be a good place to remedy that situation.
A loud grungy metal bar with ample pool tables, video games and wall-to-wall murals. It also features a photo booth and a 4 AM closing time, so things tend to get sloppy in the best way possible.
Maria's Packaged Goods & Community Bar
Part liquor store, part local tavern, this place is a perfect mixture of spooky (it features an unsettlingly large doll collection) and dive-y, and the bartenders know their shit. The beer selection is wide and varied and rotates in and out frequently. It's not huge—get ready to make some new friends while squished up against some strangers waiting for a drink—but there is a pretty sweet patio situation in the summer.
The Broken Shaker
Located inside the Freehand Chicago, this bar/lounge is basically a Wes Anderson movie set come to life. The cocktails are dangerously strong and tasty, the vibe is quirky chic, and the crowd is young and exceptionally chill given the River North location. Plus, if you drink too much, you can just book a cheap room upstairs and sleep it off.
Chicago is a Polish town, and this is a damn good Polish dive. It's got it all: the classic dive bar smell, dirt cheap drinks, a bumping 90s selection on the jukebox, pool, and the occasional free shot if you speak Polish. If not, try to keep up anyway and befriend the regulars, who tend to be a tough bunch of rowdy older Poles.
It is cash only and rarely packed, and it's a great place to take anyone you've just started dating to test their street cred. If they can't handle the vibe at Zakopane, how are they going to handle your naked body? Probably not well.
Think back to the person your childhood self imagined you would be as an adult. A person who actually has their shit together, who can taste the difference between various kinds of beer, who has a group of smart and interesting friends who meet up and smile knowing, adult smiles at each other at least once a week.
You are probably not that person, but hanging out at Hopleaf will make you feel like you are for a brief, shining moment. It's got high ceilings, lots of light, a wood cabin vibe, a vast international draft beer selection, a sweet summer patio and fucking delicious food. Another major perk is that, although it is a top-notch eatery, absolutely no one under 21 is allowed, so no screeching babies or surly teens can salt your drinking game.
Town Hall Pub
This dive haven is smack dab in the middle of the Boystown club cluster and a godsend for anyone who needs a momentary break from the MDMA mayhem but doesn't want to stop drinking (or doing drugs: the bathrooms are singles). Town Hall almost always features a drink special that's reminiscent of your college house party days—think jello shots, pudding shots, and vodka gummies. The jukebox is bumping, everyone sings along if you pick a banger, and the photobooth offers enough weird framing options to fit any occasion.
Big Chicks is brunch haven Tweet by day, and a gay dance party bonanza by night. When the sun is out, the food is heavenly, the bloodies are on point, and the coffee is strong AF. But the real fun begins when darkness falls: with Bear nights, monthly trans and genderqueer raves and queer musical events, this is always a great place for LITERALLY ANYONE to get their drank on.
Essentially three different bars for the price of one, Matilda is a good place to go if you've got a big group of friends with different drinking styles. The front bar's got a neighborhood restaurant vibe and great food, the side is dark and intimate, and down a set of dangerously steep steps is a party bar reminiscent of the classiest frat basement you can imagine. The DJ spins classic 80s/90s/00s hits all night, and crowd (who are all over the age of 23 due to Matilda's entrance requirements) happily grind all night.