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.

It may be the least secret “secret bar” in Chicago, but damn if it ain’t still one of the finest. This veteran Wicker Park institution has long been known as a pioneering cocktail bar, and is a must for any mixology enthusiast. The vibe is polite and not rowdy, which some have deemed pretentious, but just don’t act like a jerk and you’ll be fine. They also host tastings, classes, and even offer globe-trotting three-month cocktail subscriptions.

One of Chicago’s oldest bars, this 1907 original served as notorious gangster Al Capone’s favorite Prohibition-era hangout. These days, Green Mill remains one of the top jazz clubs in the country as well as a damn fine spot to grab a drink. The cinematic vibes of this bucket list-worthy bar are impossible to miss (with several film scenes being shot here), especially when bands hit the old-timey stage. It’s also a top post-show spot after catching a concert at the nearby Riviera or Aragon.

This erstwhile Bridgeport establishment is well known as one of Chicago’s premier “slashies” (half bar/half liquor store), but the vibe is slightly more upscale than the inimitable genre’s usual dive aesthetic. The hip, artsy space features beer bottle chandeliers and a mind-boggling selection of 500-700 craft beers between the bar and bottle shop (making it easily one of the best beer bars in the city as well as a leading South Side institution).

Hey, hey you. You like to booze? You like to booze while trying to properly identify the flag of Bolivia? Then you’ll love Map Room, one of Chicago’s OG craft beer kingpins that’s been doing its thing since 1992. This “traveler’s tavern” has aged gracefully, retaining its laid-back ethos while still managing to curate one of the most interesting beer selections in town.

Whether you’re looking for a secret bar, a beautiful bar, or a tiki bar, Three Dots and a Dash is the place for any occasion. Known for serving up some of the strongest drinks in the city, alongside boozy slushies, much ink has been spilled in this fair publication regarding this uber-popular River North tropical emporium in the past. But that’s because it’s still one of the flat-out best bars in the city, with 200+ rums adrinks like treasure chests packed with booze and dry ice.

Expect the unexpected at this high-end cocktail laboratory from world-renowned chef Grant Achatz, where the drinks are pieced together as meticulously as the dishes in a Michelin-starred restaurant. With bartenders trained as chefs and a state-of-the-art drinks kitchen, beverages here are designed as works of art with past incarnations spanning booze served in balloons, glass ships, and ice spheres.

2021 continues to be a breakout year for Bridgeport’s beloved beer overlords at Marz Community Brewing, who in 2018 opened one of the most celebrated taprooms of the year in an increasingly taproom-heavy city. What makes Marz special is their attention to detail and diehard community spirit. Marz’s 4,000-square-foot tap room features gallery space and arcade games paired with typically atypical eats like spam musubi and ube mochi waffles served in a beautiful industrial chic, art-heavy space.

There are dive bars, and then there is Old Town Ale House. Cited as the “best bar in the world that I know about” by former longtime patron Roger Ebert and frequented by everyone from Bill Murray to Anthony Bourdain over the years, this neighborhood gem sports stiff drinks, a diverse jukebox, an interesting crowd ranging from grizzled old timers to curious tourists, and plenty of stories to tell.

This massive 8,000-square-foot beer bar/music venue/community hangout entered the scene not too long ago courtesy of the crew behind The Whistler and quickly evolved into one of Chicago’s top beer bars. Occupying a former cabinet store that looks more like a neighborhood elementary school from the outside, the inside is bright and open with light blue leather bar stools and booths accenting a wooded space serving up an impressive array of regularly rotating beers on draft plus ciders and meads.

It’s no secret that the live music industry has had a rough go of it as of late, but local dive Montrose Saloon heroically managed to keep the tunes flowing throughout the pandemic with almost-daily outdoor concerts on its cozy back patio. Grab drinks from the side window, find a table, and soak up the atmosphere alongside an eclectic crew from all walks of life brought together by the simple joy of live music.