Where to Grab a Drink in Chicago Right Now

Posh hotel rooftops, natural wine newcomers, and the California Clipper retakes the stage.

Chicago’s known for many signature culinary delights—deep dish pizza, loaded brats and hot dogs, overstuffed Italian beef sandwiches, even homestyle Ukrainian pierogi, to name a few. But what’s a hearty Midwestern meal without some quality beverages to help wash it all down? That’s exactly where Chicago’s epic bar scene comes in, a veritable boozy wonderland that’s been keeping its residents in good spirits since the days of hog butchers and big shoulders. And, hell, if even pesky old Prohibition couldn’t get in the way of our notoriously speakeasy-friendly city’s collective thirst, it goes without saying that nothing can.

From low-key dives, rowdy sports bars, and romantic cocktail spots to top-notch beer bars, breezy rooftop hideaways, and fancy hotel lounges, it’s tough to chart a course through the city’s bustling nightlife landscape. So it’s a good thing we got together to curate the very best bars in Chicago to hit this spring, whether you’re looking for a cutting edge newcomer or a tried-and-true neighborhood hangout. Drink up, Chicago—there’s only a few more months until winter rears its frosty face once again.

Good Funk

Loop
$$$$

The seasoned brunch wizards who brought us hotspots Beatnick, Beatnik on the River, and Michelin-starred Porto dropped this downtown ode to natural wine back in December and were immediately met with rave reviews. Embrace the bugs inside this intimate, narrow space (formerly Cafe Bonhomme) by sidling up to the glossy marble-topped bar and perusing the stocked, ever-changing wine list curated by Bonhomme Group wine director Colin Hofer. Throw in some bougie shareables—think housemade free range Chicken Liver Pâté, Anchovy Butter Toast, and Steak Tartare with dry-aged Angus beef and confit egg yolk—and consider date night done and dusted.
How to book: Stop by for first come, first served seating.

Moonflower

Portage Park
$$$$

If you were recently wandering around the far northwest side, scratching your chin and dwelling on the fact that this stretch of Windy City real estate somehow still lacked a plant-themed drinking den, your prayers have been answered in the form of this moody Portage Park debut. Housed in the former Hops and Barley space, industry vets Zach Rivera, Marvin Boeving, and Christina Chae joined forces to bring this verdant saloon to life—quite literally. Blooming, thriving fauna dots nearly every surface, sharing space with classic cocktails (Negronis, Espresso Martinis), original concoctions (Seeing Green, a Dude-abided mix of matcha-spiked sweetened condensed milk, Jinro Soju, and vodka), and a concise menu of quirky bites like Artichoke-Pickle Dip and Bacon Cheddar Fritters.
How to book: Stop by for first come, first served seating.

Dorothy Downstairs

West Town
$$$$

Cloaked in ‘70s-era flair—wood-paneling, disco balls, pressed velvet wallpaper, an enticing array of plump burgundy-hued sectional couches and vintage lounge furniture—this queer-owned and -operated speakeasy beneath West Town fried chicken palace Split-Rail is back in action after two years of COVID-fueled hibernation. And while the lounge might lean LGBTQ+—“a friend of Dorothy” was a covert identifier for closted gay folks in the mid-20th century—this joint’s subterranean doors are open to bar-goers of any background, dubbing themselves queer-friendly rather than exclusively gay. Check your preconceptions at the door, grab a skillfully made throwback cocktail, and get into the groove Thursday through Sunday evenings starting at 6 pm.
How to book: Stop by for first come, first served seating.

The Clipper

Humboldt Park
$$$$

This beloved Humboldt Park haunt made its triumphant return to California Avenue in late February, 2022 after a sudden and heartbreaking closure two years ago. And you better believe the old-school jazzy vibes are still alive and well inside the red lit space. The new owners have painstakingly maintained the 1930s-era refuge’s ancient long wooden bar and cozy vinyl booths, keeping the ambiance simple and sultry while subtly ushering the sound system into the 21st century with a noteworthy upgrade. To pair with the sound boost, the team also converted the old C.C. Ferns space into a backroom listening lounge for sipping audiophiles. In terms of drinks, the broad list of standards that once hung above the vintage back bar has been swapped for a slightly smaller selection (though still just as tasty) plus clever house cocktails, beers by the bucket, and a coveted Suntory Toki highball machine, while the bartenders are just as talented and personable as ever.
How to book: Stop by for first come, first served seating.

The Welcome Back Lounge

Logan Square
$$$$

Opened in summer 2020 in the heart of Logan Square’s Hipster Highway, this unapologetically ‘70s and ‘80s-themed good-time emporium has everything you need for a fun night on the town… And a few things you don’t, but certainly help, like drinks served from a playfully colored bus in their cozy mural-lined patio. Inside the bar, there’s enough tacky wallpaper and checkered linoleum floors to remind you of your grade school days, served up alongside inner-childlike delights like Jell-O shots, fried bologna sandwiches, and canned wine. Order up some brats and tots during weekend brunch or head in for charity bingo on Monday nights, benefiting a different organization every month.
How to book: Stop by for first come, first served seating.

Bar Goa

River North
$$$$

Escape the same-sameness of the River North bar scene at this vibrant spot named after the so-called “Ibiza of India.” Bright coastal colors and tropical vibes greet visitors to this lively gastropub marrying Portuguese and Indian flavors via dishes such as Pork Vindaloo Sliders and Goan Chicken Curry. Entertainment includes live comedy and EDM-focused DJs, and don’t leave without trying their international version of the Chicago Handshake (known as the ChicaGOAN Handshake), which swaps the Malort for the infamous Goan cashew brandy Feni. While it’s not quite as pungent as the Midwestern wormwood thriller, you might still end up making this face.

Available for Reservations

Ludlow Liquors

Avondale
$$$$

It’s been nearly three years since it was named one of the Best Bars in America by Esquire, and in that time, many trends have come and gone. But drinking in a cool, dimly lit bar never goes out of style. Ludlow continues keeping it real in low-key retro-chic environs aided by an affable picnic tables- and murals-ensconced patio and one of the most underrated bar burgers in the city. The loaded fries are also no joke, although slightly more adventurous diners might want to try their hand at something like the Ratatouille Parm Sandwich. Drinks are done right and without pretension, with classics like Old Fashioneds and cans of Hamm’s high on the agenda. Don’t think too hard about it—just go.
How to book: Stop by for first come, first served seating.

Bokeh

Albany Park
$$$$

This chill hang just north of the Kedzie Brown Line stop in the slowly but steadily increasingly cool Albany Park neighborhood may not be the craziest bar in the city, but that’s kind of the point. Brick walls and a minimalist vibe cultivate an air of relaxed sophistication as you dive into standout cocktails with which you might not be overly familiar, such as the signature Fernet-based Bokeh or a barrel-aged Seaweed White Negroni (it’s better than it sounds). Cocktail flights, DJs, and rotating art shows round out the imbibing experience alongside eclectic late-night small plates such as Smoked Trout Dip, Cubanos, and Mac and Cheese Salad. While you’re here (and looking to stay on your best behavior), try one of their actually quite decent mocktails for good measure.
How to book: Stop by for first come, first served seating.

The Whistler

Logan Square
$$$$

One of Chicago’s top cocktail bars, this joint is as hipster-friendly as it is booze savvy, featuring live music paired with an ever-changing drinks menu made up of classics and Whistler originals. In case that wasn’t cool enough, the walls are adorned with monthly rotating art installations from local artists, which you can peruse while contemplatively stroking your scraggly leftover winter beard with a cocktail in hand.
How to book: Stop by for first come, first served seating.

The Hideout

Elston Industrial Corridor
$$$$

Life can get tough. Times can get dark. But the Hideout exists, so all's right with the world. Easily one of Chicago’s most truly magical spaces, live music and other oddball events (competitive reading, anyone?) take center stage at this beloved 1890s-era dive where a good time takes a bit of effort to miss. So stop wasting any more time dilly-dallying at other bars and head straight for that beckoning Old Style sign.
How to book: Stop by for first come, first served seating or purchase concert tickets online.

Billy Sunday

Logan Square
$$$$

This cocktail classic has been mixing 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 gin-packed Kent, seasonal standbys like the Hot Buttered Rum, or “Billy Beloveds” like the Scotch-based Penicillin. This is drinking as drinking was meant to be.
How to book: Reserve via Tock.

This breezy hotel hang has been serving high-minded yet unpretentious cocktails to a diverse crowd inside 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 heroes like Maplewood, Off Color, and Whiner.

Available for Reservations

Victor Bar

North Center
$$$$

Well, this place is a surprise. Popping up in North Center—a neighborhood not exactly known for upmarket mixology—Victor Bar is a veritable oasis amid 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.
How to book: Stop by for first come, first served seating.

Osito’s Tap

Little Village
$$$$

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 mixological offerings. They’ve got DJs and brunch. They’ve got cocktails and micheladas. They’ve got tacos and Mexican snacks. More importantly, they’ve got a clear winner on their hands.

Available for Reservations

Pilsen Yards

Pilsen
$$$$

One of the most buzzworthy developments during the (still ongoing?) 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 wooden tables set the scene for a laid-back sip session fueled by delicious margaritas, elevated pub grub, and local classics like the Chicago Handshake. Stop by for weekend vinyl sets and bask in the recently opened bar-within-the-bar The Alderman, an intimate 18-seat cocktail lounge with drinks curated by award-winning mixologist Lance Bowman.

Available for Reservations

Scofflaw

Logan Square
$$$$

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 lineup, order any drink, and rest assured knowing it’s pretty much guaranteed to knock your socks off (if you’re wearing any). And—bonus—you’ll feel like you’ve expanded your horizons in the process. While the bill is famously gin-focused, there’s plenty of non-gin offerings like the bourbon-based Caro Kahn or daily punch specials in addition to a hearty offering of craft brews and spirits.

Available for Reservations

Hopleaf

Andersonville
$$$$

Long known as one of the best beer bars in Chicago, this lively Andersonville 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 like Spiteful and Dovetail. They’re also slinging wines on tap along with anything else you could possibly feel like drinking. No TVs. No reservations. No BS. Just sit down and drink.
How to book: Stop by for first come, first served seating.

The Violet Hour

Wicker Park
$$$$

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 remains a must for any budding mixology enthusiast. The vibe is polite and not rowdy, which some have deemed pretentious, but don’t act like a jerk and you’ll be fine. They also host tastings, classes, and even offer private events and classes, so you too can one day learn the ways of the master mixologist. Might want to throw on a vest for this one.
How to book: Reserve via Tock.

Green Mill

Uptown
$$$$

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. Drinks are nothing too fancy or gimmicky, just strong and delicious. Just don’t chat too loud while the bands are playing or you will be unceremoniously shushed.
How to book: Stop by for first come, first served seating.

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 divey aesthetic. The hip, artsy space features beer bottle chandeliers and a mind-boggling selection of 500 to 700 craft beers between the bar and bottle shop (making it one of the best beer bars in the city as well as a leading South Side institution). Yet their cocktailing game is no slouch either, with offerings including the tropical Royal Wailuku.
How to book: Stop by for first come, first served seating.

The Map Room

Bucktown
$$$$

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. Leaf through weathered copies of National Geographic, try to drink beers that correspond to the various flags hanging from the ceiling or, better yet, belly up to the bar and plan your next trip with a new friend.
How to book: Stop by for first come, first served seating.

Three Dots and a Dash

River North
$$$$

Whether you’re looking for a secret bar, a beautiful bar, or a tropical 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 whimsical ventures like 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, regardless of category, with 200+ rums, drinks like treasure chests packed with booze and dry ice, and tasty Polynesian bites like Coconut Shrimp and Thai Fried Chicken. For an extra special experience, snag a seat in the Bamboo Room, the intimate bar-within-a-bar where beverage director Kevin Beary unleashes his specialty rum prowess on thirsty diners.
How to book: Reserve via Tock

The Aviary

Fulton Market
$$$$

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. It’s not a cheap night out by any means, but it’s ideal for those evenings when you need to impress someone who isn’t easily impressed (i.e. expect to splurge).
How to book: Reserve via Tock.

 

Marz Community Brewery

Elston Industrial Corridor
$$$$

2022 should continue to be another 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, offering a robust lineup of offbeat offerings like their King Kona vs Marzilla imperial stout to complement more traditional staples like The Machine and Bubbly Creek. Led by the indefatigable owner of Maria’s Packaged Goods and Kimski (who also runs an art gallery and a radio station while publishing two indie publications, no big), Marz’s 4,000-square-foot tap room features a gallery space and arcade games paired with typically atypical eats served in a beautiful industrial chic space just minutes from Guaranteed Rate Field. (Pro-tip: Northsiders can now have their Marz and drink it too at the still new-bar-smelling Life on Marz Community Club in Bucktown.)
How to book: Reserve via Tock.

Old Town Ale House
The Old Town Ale House | Goya60 / Flickr

Old Town Ale House

Old Town
$$$$

There are dive bars, and then there’s 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. The bar is equally famous for its walls, lined with longtime owner Bruce Elliott painted portraits of everyone from a nude Sarah Palin holding a rifle to a mid-strip-search Rod Blagojevich.
How to book: Stop by for first come, first served seating.

Sleeping Village

Avondale
$$$$

This massive 8,000-square-foot 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 barstools and booths accenting an impressive array of regularly rotating beers on draft plus ciders and meads. With a state-of-the-art sound system and a mostly local lineup of independent musical acts, the 300-capacity venue gives way to a roomy 150-person year-round patio providing you plenty of time and space to linger.
How to book: Stop by for first come, first served seating.

Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile.
Meredith Heil is a Senior Cities Editor at Thrillist. She's originally from St. Louis, now lives in Chicago, and in between has been to all 50 states (that's boots on the ground, no airport BS). She enjoys all things cocktails, crosswords, and women's soccer. Challenge her to a game of Hoop Shot at @mereditto.