This cocktail classic has been slinging expertly crafted libations for what feels like ages, and these folks clearly know what the hell they’re doing behind the stick—just try and stump them. Or, better yet, order batched gems on draft like the summery Parcha Punch #3, seasonal standbys like the Summer of ’49, or “Billy Beloveds” like the Billy Sunday Old Fashioned. This is drinking as drinking was meant to be.

This good-time emporium has been serving high-minded yet unpretentious cocktails to a diverse crowd at upscale hostel (AKA “poshtel”) Freehand Chicago for years now. Taking cues from their original Miami location, these Tales of the Cocktail Best Hotel Bar-winners mix up fun tipples like the rum-based Camping on Acid and Mezcal-infused Velvet Revolver to pair with a small but well curated selection of brews from local heros like Maplewood, Off Color, and Half Acre.

Well, this place was quite a surprise. Popping up in Northcenter—a neighborhood not exactly known for upmarket mixology—Victor Bar is a veritable oasis amidst the sea of Miller Lites and jalapeno poppers lapping up against the corner of Damen, Irving Park, and Lincoln. The Parisian-inspired cocktail lounge is dark, sexy, and perfect for one of those awkward “getting-to-know-you” first dates. Sip on some French wine, knock back a few cocktails, and voila—suddenly, you have taste.

Since when is a rooftop bar a bad idea? As the answer is clearly “never,” the idea gets even more pronounced when said rooftop is this new-ish hotspot perched above Robert DeNiro’s fabled Nobu Hotel Chicago. YOLO the night away feasting on sushi, King crab mini tacos, and ribeye sliders paired with exclusive sake and champagne. Hey, gotta cash in that AMC stock at some point,right?

Opened all the way back in 2019 (remember those days?), this hotshot speakeasy-inspired hang brings modern Latinx flair and top-notch cocktailing to a neighborhood traditionally lacking in such offerings. They’ve got DJs and brunch. They’ve got cocktails and micheladas. They’ve got elote ribs and beef michada. More importantly, they’ve got a clear winner on their hands.

This new Logan Square brewpub from Highland Park-based Ravinia Brewing is a chill hang for craft beers paired with Mexican street food like hand-pressed tacos and tortillas. What’s not to like? Choose from offerings like their Food Truck pilsner, Diversey Station pale ale, and Frank’s Fusion hard seltzer as you kick back and relax. They call it “unpretentious beer for unpretentious people,” which is pretty damn accurate.

One of the most buzzworthy developments during the COVID-era has been the opening of this hipster hub in the even hipper Pilsen neighborhood, where simple art-lined walls with exposed brick and wood tables set the scene for a laid-back booze session fueled by delicious margaritas, elevated pub grub, and local classics like the Chicago Handshake. Stop by for weekend vinyl sets and hang in new bar-within-the-bar The Alderman, an intimate 18-seat cocktail lounge.

Patio season isn’t patio season without at least a few sunny post-ups at Parson’s, where the perennially buzzing outdoor expanse has served as the backdrop to many a warm-weather Chicago evening. Play some pong, sip a Negroni slushy, eat some chicken—you know what to do. Once an excellent reward after a stroll along the nearby 606, Parson’s has recently expanded its empire with locations in Lincoln Park, West Town, and Andersonville. Bar crawl anyone?

This longtime Logan Square institution is the kind of place you can visit not knowing anything about the drinks on the menu and leave with a feeling of accomplishment. That’s because you can throw a dart at the menu, order any drink, and rest assured knowing it’s pretty much guaranteed to be good. And, bonus, you’ll feel like you’ve expanded your horizons in the process. While the menu is famously gin-focused, there’s plenty of non-gin offerings like the rum-packed Swizzle 33.

Long known as one of the best beer bars in Chicago, this lively Andersonville neighborhood mainstay has been going strong since 1992 and shows no signs of slowing down. Their famous mussels and fries is bucket-list worthy when it comes to Chicago cuisine, with additional options from the Belgian-inspired kitchen including a brisket reuben and toasted Nueske ham. With 68 taps and more than 400 beers in bottles, the draft list is heavy on Belgians while paying homage to several local brewers.