Mary K’s Guide to Chicago Nightlife

Somehow, a few wild nights in Chicago captured on Snapchat have earned me the reputation of a party girl who knows the best nightlife in the city. Often, I feel like the cis Stefon when people ask where they should go out. I tell them, “Chicago’s best rooftop bar is…” while curled up in bed with a good book, trusting that they’ll still have a good night without me.

Alas, I’ve compiled a list of the best spots to hit up by neighborhood. Enjoy, and keep in mind that I have never once paid for a full-priced drink in Chicago. That shit’s expensive.

(PS this is not a sponsored post. These are my honest opinions!)

Old Town

Old Town is the place to be if you’re a recent grad and want a “chill” night out without puking college students. Dress code is flexible at most places — you can be casual after your softball league or you can be in clubbing attire. Benchmark, Pour House, Woodie’s Flat, and Hopsmith are all favorites. It’s not the most diverse crowd, though — be prepared to hear white people singing Sweet Caroline at least some point in the night.

River North

If you’re tryna club, head to River North. Hubbard Street is the hub of nightclubs, and I like Joy District and the Bottled Blonde best. If you’re trying to get into SHAY, Studio Paris, or any of the legit nightclubs, make sure you know a promoter or else you’re going to be waiting in line all night. Don’t get there before 11 or 12 because you’ll be out ’til 4AM anyway.

Three Dots and a Dash is a well-known tiki bar speakeasy, if there is such a thing. If you’re feeling country, you can always go to Concrete Cowboy or Bub City (live music but cover, ew).


Sigh. Wrigley is the ratchet place we went to college because they didn’t strictly card (Disclaimer: I never had a fake ID, which was definitely for the best, but I had a lot of younger friends). Between wannabe frat stars and random Cubs fans, you have to be dRuNk to handle it. Loyola’s bar was Irish Oak, which is fun if you’re into singalongs. Once, I sang and danced to a Lion King theme song remix. Hell yeah. My personal favorite is Deuce’s and the Diamond Club, which is the most club-like. With two stories and an outdoor patio, it can get crazy during warm weather. Others might recommend Old Crow or Slugger’s, but seriously RIP Red Ivy. </3

Lincoln Park

I live in Lincoln Park, but so do DePaul students so I seldom go out here. If I do, I usually end up at Prysm. Not only is it a short walk from my apartment, but it’s also my favorite club in the city. For a night that doesn’t require six inch heels, Lincoln Avenue is always a blast. I recommend starting downstairs at the Lion’s Head Pub, then going upstairs to the Apartment once you’re drunk enough to handle a legitimate dance floor. Lincoln Park has the best late night food too: as you’re walking back to the Fullerton stop, pick up your go-to Mexican at Allende.

West Loop

I’ve never actually been out at night in West Loop, but I love West Loop. If you’re looking for a Sunday Funday day-drinking excursion, go to West Loop. Start with brunch at the Publican, then make sure you go to Federales for a signature shot: tequila in an ice glass and throw at a bell. If you do want to go clubbing, find a promoter and hit up the MID.


Rooftops are my THANG and I am constantly hunting for new skyline views. Not only is Joy District a fun club, but it also has a gorgeous rooftop. Rock Bottom is a great place to take your parents and eat some yummy food. In Lincoln Park, J. Parker is bougie but worth it. However, I recommend going to the Cabana Club at the Robey Hotel in Wicker Park. The unprecedented #VIEWS are far enough away from the city that you can really soak it all in. It’s also right by a Stan’s Donuts sOoOo…

I’m typically in bed by 9PM, but on special occasions, you’ll find me out ’til 4AM dancing my ass off. I hope you have as much fun as Blackout Mary has at each of these bars/clubs!

++ Mary K

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