One day, someone will ask you where you go out, and you’ll just stare into space for a second or two and then say, “I don’t.” This might happen when you’re 23 or it might happen when you’re 63. If it happened already, this guide’s for you.
Below you’ll find two lists of options. The first has a bunch of relatively calm bars that are trendy but not too sceney, and the second has some places where people who don’t need this guide already know they’re supposed to go.
CALMER BARS WHERE NO ONE WILL SPILL A DRINK ON YOU
The Pink Squirrel’s theme is “Midwestern culture,” but unlike your uncle who lives in Wisconsin with his taxidermy collection, this place is actually very cool. They serve retro drinks you’ve probably heard of but might not have tried (like Harvey Wallbangers), along with things like gimlets and Old Fashioneds. The space is low-key, and has plenty of diner-style booths that make getting a seat pretty easy. There’s even duckpin bowling in case you get bored with just drinking.
The last time you were a regular someplace, you were happy sharing whatever was in the communal pitcher. But now you like having your very own beverage, and are ready to have a new spot where people recognize you. Spilt Milk in Logan Square is the kind of laid-back neighborhood bar you’re looking for, where everyone (including the bartenders) is really friendly. There’s a great outdoor patio that’s perfect for groups, and when it’s not nice outside, the interior is dark and cozy, decorated with little candles you can pretend are tiny fireplaces.
If you still have terrible memories of spring break and sugary drinks from Senor Frog’s, you might not be very excited about tiki bars. And while Lost Lake in Logan Square is full-blown tiki (including bamboo chairs and floral wallpaper), its tropical cocktails are well-balanced and delicious. The space isn’t very big, so you might have to wait for a table - but once you get one, you’ll want to stay there.
This Logan Square spot feels like an old tavern, but is actually pretty trendy (we know this because the drink menu includes a bourbon root beer float with fernet ice cream). But if you’re afraid of trying new things, or just like your alcohol to be ice cream-free, you can have some very good classic cocktails here, too. It gets crowded (but not so crowded that you won’t be able to find a seat), and they actually serve really good small plates.
Going to a tiki bar in River North might not sound like the best first move for someone who (like you) doesn’t go out anymore - after all, this is the sceniest neighborhood in Chicago. But even though this place serves cocktails in mugs shaped like pineapples and mermaids, it manages not to be obnoxious or completely full of tourists. This is helped at least a little bit by the fact that the entrance is hard to find (it’s hidden in an alley). All that being said, you can absolutely order a $385 smoking Treasure Chest here if you feel like it.
Wine bars in general might make you think of boring lectures on varietals and/or the characters from Sideways, but The Press Room doesn’t really fit this stereotype. It’s very laid-back, and rarely crowded because it’s hiding in the basement of a building in the West Loop. They have a wide range of wine options, but also really good cocktails, and a short small plates menu that goes well with both. This is an easy place to hang out all night.
You’re tired of drinking in your house, but you still like the idea of drinking in a house. Go to Scofflaw in Logan Square. It looks a little like a living room, and you can enjoy a few of the generally gin-focused drinks while sitting around a fireplace. Plus, they give out free freshly-baked chocolate chip cookies after midnight. So there’s a pretty good chance that hanging out here is better than hanging out in your actual home.
The “House Rules” at this spot in Wicker Park (which ban baseball caps, Cosmopolitans, and any drink that’s a -bomb, jager or otherwise) manage to keep it pretty low-key inside. It really feels more like a lounge than a bar - it’s dark, with lots of candlelight, comfy chairs, and tables that can be sectioned off for privacy. Just know that the door is unmarked, so it might be a little hard to find. But it does exist, we promise.
Busier Places For When You Really Want To Go Out
Celeste is in River North, and it has four levels, each with its own theme. The third floor is a little swanky, with chandeliers and a couple of curtained booths for groups, and the rooftop level is designed to feel like a garden, with plants and marble tables all around. But when you really want to go all out, hit the dance club “disco floor,” which is pretty self-explanatory.
If you want music and a crowd, but not someplace that could possibly be a filming location for The Real Housewives of Schaumburg, you should know about The Bassment in River North. This club has live jazz, DJs (sometimes both on the same night), and plenty of space to dance. But if dancing sounds like a bad idea, they also have big leather chairs and couches. Another thing to know: they have a “bathtub gin” drink that comes in a tiny bathtub.
You definitely want to go out out, and also go back to the time when the biggest responsibility you had was folding T-shirts at the mall. Go to Esco Bar, the club on the top of Ronero in the West Loop. This place is full of people who give absolutely no f*cks - as in dancing on tables, and seemingly worrying about nothing (including general table safety). An hour here and you’ll forget about that condo assessment in no time.
Yes, this is a pizza restaurant in the West Loop. But on weekends it happens to be full of crowds who are way more interested in drinking than eating the average pies. And because it has two huge outdoor areas (a patio and a rooftop), you won’t have to compete to get a seat outside. You will have to compete to be heard, however, so just come prepared to shout your conversation.
Chicago is definitely more of a bar city than a big club city. But sometimes just you want to go a multi-level spot that has long lines to get in, fog and light machines, and a packed dance floor. Somewhere you can go dancing until 4am and/or relive that trip to Berlin you took after college. Prysm in Lincoln Park is where you can do this and actually have a good time. Then you can back home and remain dormant until you need this guide again.