Yes, it’s really an old janitor’s closet
For those who have always wanted to get boozy in a janitor’s closet, you’re in luck. This intimate 15-seat speakeasy in the lower level of the FieldHouse Jones is just that. Used as an actual janitor’s closet when the building housed the Borden Dairy Depot before it was converted into a hotel, the space pays strong homage to its roots with mop heads on the walls, janitor tools on the bar, and menus printed on rags. Enter through the “Employees Only” sign to uncover a playful, experimental rotating cocktail menu focused on house-made syrups and infused liqueurs paired with local brews from Middle Brow and Hopewell, bizarre esoteric wines, and eats from 5411 Empanadas. Reserve a spot ahead to guarantee a seat.
Explore the tastes of Japan from the comfort of your barstool
One of the most talked-about openings of the past year is this hip Japanese-inspired outpost with drinks helmed by bar star Julia Momose and eats courtesy of Michelin-starred chef Noah Sandoval. Grab a spot at a table in the bright and cheery space or slide into the intimate eight-seat bar to dive into the seven-course tasting menu (think caviar, sashimi, fluke) with optional beverage pairings curated by Momose. You can also order “little luxuries” (aka small bites) like steam buns, chicken liver, and tempura prawns to taste while you explore a booze menu packed with rare Japanese whiskies, sake flights exploring different regions of Japan, and 10 different highballs. There’s also a stout assemblage of nonalcoholic mixed drinks for those who’d rather keep their wits about them.
Live bands and booze in a cool subterranean lair
This cool subterranean space in the even-cooler Hoxton Chicago pairs a deep menu of 52 cocktails with live music on weekends in a beautiful space that gives off something of an upscale ‘60s basement vibe. With a baby grand piano, candlelit tables, plush sofas, and banquettes, as well as books and maps of Chicago, you can elect to go traditional with a negroni, daiquiri, or salty dog or try something slightly more inventive like the Irish whiskey, dry vermouth, and absinthe-infused Blackthorn or the Clover Club (gin, raspberry syrup, lemon, egg white). The dark, sexy space is a clear winner for a date night done right, especially when live bands are playing. Chalk up another hit for Boka Restaurant Group.
Drink like a king in this royalty themed, Insta-friendly playpen
This delightfully weird “spirits lounge” offers a much-needed respite from the same-old sports bars and charmless frat bro haunts that have long dominated Lincoln Park’s main drag. With nightly tarot card readings, a royal throne flanked by a suit of armor, fancy chandeliers, and framed portraits of folks like Elvis and Bowie, the space certainly has a flare for the dramatic. Grab some wine on tap, large-format cocktails (which they call “king size”), or drafts from 3 Floyds and Dovetail as you marvel at the royalty-themed space that carries more than a passing resemblance to something out of Game of Thrones. Drinks include the Grand Poobah (vodka, aloe liqueur, watermelon, lime, mint), the Boss Daley with rye whiskey, apple brandy, and sweet vermouth, and the tiki-style Tuff Gong packed with three types of rum.
Kind of like a tech startup… for beer
This “brewing incubator” and tasting room is unlike any beer bar you’ve probably been to. Helping breweries pilot new projects with experimental beer recipes, styles, concepts, and collaborations, the community-focused microbrewing facility is kind of like a WeWork office or food hall for beer. The rotating list of partner breweries currently cooking up sudsy concoctions for you to try in the café-style bar include food-inspired beers from Brewer’s Kitchen, rare wine/beer hybrids from Tethered Vines, and Scandinavian-inspired brews from soon-to-open Humboldt Park brewer Orkenoy. Get there early for $1 drip coffee before 9am with a smattering of eats available throughout the day including artisanal waffles, cookie flights, and offerings from rotating food trucks.
Glamping in your own boozy tent across from Wrigley Field
This seasonal pop-up currently running through late February is not your typical bar experience. It’s a full-service “glampsite” with private glamping tents set up on the terrace of the Hotel Zachary. What does this mean? It means there’s no better place for you and up to nine friends to drink barreled, large format cocktails like Oaxacan Old Fashioneds, spiked hot chocolate, and/or hot toddies overlooking the winter wonderland that is Gallagher Way adjacent to Wrigley Field (where there will be ice skating, holiday markets, and seasonal events this winter). Each luxury canvas tent includes fire cauldrons, holiday décor, plush couches and more highly Instagrammable fare, with casual eats available from The Bar at Hotel Zachary. Camp Zachary reservations are required for $150 per two-hour interval, with the cost added to whatever you spend on food and booze.
Finally, a governmental entity you can drink in
Themed after that infamous governmental entity that apparently “you can’t fight,” this West Loop hang pairs local bar Recess with 10,000-square-foot industrial chic event space City Hall. Stop by Recess for “Ticket Tuesdays” (when you can bring in a parking ticket for 20% off), live music Fridays, or Saturday brunch (when they’ll be serving drinks like the Crook County Cocoa topped with a donut hole, chocolate cookie, rainbow sprinkles, marshmallow, and whipped cream). Several of the cocktails like the gin-based Southside or tequila-packed Alderman’s Choice can also be made spirits-free or CBD-infused, while the bar is also serving up shared cocktails in water coolers like the Rum Emanuel and mixed shots such as the Stolen Election made with rum and tropical Red Bull. Food runs the gamut from staple bar eats like burgers and grilled cheese to more out-there items like a double crust Amish pot pie.
Longtime neighborhood wine shop reinvents itself as a wine bar “slashie”
After 15 years as the South Loop’s premier wine and beer retailer, this beloved neighborhood bottle shop has recently added a wine bar to reinvent itself as a true wine shop “slashie” (half bar/half liquor store). Stop by for live music during Friday happy hour (4-6 pm), bring your own jams for BYOVinyl night on Wednesdays, or enjoy free wine tastings on Tuesdays along with free craft beer tastings on Thursdays. Sip from an eclectic hand-picked selection of wine (with a focus on organic fermentation), local and rare craft beer on tap paired with boutique whiskeys and spirits with a diverse crowd of wine enthusiasts and neighborhood locals in a relaxed yet lively wood-floored space with tables set up throughout the bottle shop. The best part? If you like what you’re tasting at the bar, take home a bottle for half price. It’s called multitasking.
It’s good to get creative at this gin-focused cocktail “salon”
This longtime Logan Square institution is the kind of place you can walk in not knowing anything about the drinks on the menu and walk out 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 you’ll feel like you’ve expanded your horizons in the process. While the menu is gin-focused, there’s plenty of non-gin offerings like the bourbon-based Sea Quake and the mezcal-infused Hearth Tax in addition to craft brews and daily punch specials. Sip your latest concoction at the bar overlooking the street or hit up the Victorian-style “salon” room by the fireplace as you tear into a food menu offering everything from burgers and ice cream sandwiches to steak tartare tostadas and weekend brunch.
Mussels, fries, and Belgian brews in a classic neighborhood pub
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 fried catfish hoagie and duck reuben. 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 Metropolitan and Maplewood. They’re also slinging wines on tap plus ciders, meads, and anything else you could possibly feel like drinking. No TVs. No reservations. No BS. Just sit down and drink.
Enter through the mural to find some of Chicago’s best cocktails
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 Chicago 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 an asshole and you’ll be fine. Select cocktails from the “shaken” or “stirred” side of the menu while sipping expertly crafted libations like the whiskey-based Neutral Ground or the tequila-infused Shitzu Sling amongst clusters of candlelit tables and a long marble bar. They’re also offering cocktail classes, cocktail kits, and cocktail demos if you want to nerd out a bit more on their James Beard Award-winning bar program. Locate the entrance from the door handle hidden inside the exterior mural.
Elston Industrial Corridor
Live indie bands and good times in a beloved local dive
You’d be hard pressed to find anyone in Chicago who didn’t visit this out-of-the-way little bar and immediately fall in love with the joint. Located in an industrial section of the Elston Industrial corridor and operating legally since 1933, the endlessly charming bar/music venue is located inside an 1881 balloon-frame house with little to denote its existence other than a vintage Old Style sign out front. Having emerged as one of Chicago’s leading indie rock venues in more recent years, the bar is simply one of the most fun places to grab a drink in Chicago -- especially when live bands are playing the twinkling light adorned back music room. With additional events ranging from storytelling to live interview shows, you’re always guaranteed to meet some interesting characters here.
Sip cocktails in style at this iconic former mobster hangout
Opened in 1907 as one of Chicago’s oldest bars and famous for being the one-time favorite hangout of Al Capone during Prohibition, these days Green Mill is one of the top jazz clubs in the city as well as a damn fine spot to grab a drink. The cinematic vibes of the bucket list-worthy bar are impossible to miss (with several film scenes being shot here), especially when jazz bands hit the old-timey stage. A favorite post-show spot after catching a concert at the nearby Riviera or Aragon, just don’t be too loud or rowdy while the bands are playing or you will be loudly and unceremoniously shushed. Drinks are nothing too fancy or gimmicky, just strong and good. Green Mill also hosts the long-running Uptown Poetry Slam every Sunday night in addition to a weekly “live magazine show.”
One of the hippest spots in town also serves a mean cocktail
With an in-house record label, rotating art installations, live music/DJs seven nights a week, and a daily changing menu featuring some of the finest cocktails in Chicago, there is perhaps no cooler bar in Chicago than The Whistler. Sure, it’s been around a while and doesn’t have that brand new smell of many cocktail imitators. But it continues to do what it does, and does so well. The award-winning cocktail program focuses on classics, contemporary favorites, and Whistler originals, while additional non-music events include “movieokie,” film screenings, and readings. The small bar is usually packed, especially on weekends, and somehow still offers consistently reasonable cocktail prices that are often cheaper than the competition. And these days in Logan Square, there’s plenty of competition.
Stiff drinks and surprisingly good eats at this neighborhood dive
Some bars you just know are cool the second you walk in. Skylark is one of those bars. This longtime hipster favorite doesn’t offer much in the way of the superfluous. And that’s the way longtime regulars like it. Clearly not trying too hard (or hardly at all), this Pilsen neighborhood dive offers a retro feel, stiff cheap drinks, and, shockingly, some of the best food at any dive in Chicago. Don’t be put off by its scruffy exterior. The kitchen here is legit. Tater tots are the most popular items, but additional options including everything from cod po’ boys to jerk grilled chicken depending on how adventurous you’re feeling. The beer list isn't huge, but it's solid with many local offerings including Lo Rez, Off Color, and Pipeworks.
A Bridgeport institution and leading Chicago “slashie”
This erstwhile Bridgeport establishment is well known as one of Chicago’s premier “slashies” (half bar/half liquor store), but its vibe is slightly more upscale than the dive aesthetic prevalent amongst many of its slashie compatriots. The hip, artsy space features beer bottle chandeliers, some of the best DJ nights in the city, 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). Yet their cocktailing game here is no slouch either, with well-crafted classics like the 11th Ward Old Fashioned to pair with Korean-Polish street food from on-site counter service restaurant Kimski. What more do you need?
Chill feels and international flavors at this craft beer OG
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 vibe while still managing to curate one of the most interesting beer selections in town via 26 taps and 100+ bottles. Leaf through weathered copies of National Geographic, try to drink beers that correspond to the various international flags hanging from the ceiling, or enroll in their long-running beer school to further your “adult education.”
Tiki mainstay now offering a bar within the bar
Whether you’re looking for a secret bar, a beautiful bar, or a tiki bar, Three Dots a Dash is the place for any occasion -- whether that is a search for the strongest drinks in the city, boozy slushies, or a bar to throw your birthday. Clearly, much ink has been spilled in this fair publication regarding this uber-popular River North tiki emporium in the past. But that’s because it remains one of the flat-out best bars in the city, regardless of category, with 200+ rums, inventive tropical drinks like treasure chests packed with booze and dry ice fog, and Polynesian eats like pu-pu platters and king crab rangoon. While the bar is becoming more well known amongst the tourist crowd in recent years, you can now escape from the masses at the new bar-within-a-bar that is 3 Dots’ recently opened Bamboo Room, where you’ll find more “refined” cocktails and a more intimate feel.
Splurge on eye-popping cocktail art experimentation
Expect the unexpected at this high-end cocktail laboratory from world-renowned chef Grant Achatz, where the drinks are created as meticulously as the dishes in a four-star restaurant. With bartenders trained as chefs and a state-of-the-art drinks kitchen, cocktails here are designed as works of art -- with past incarnations including drinks served in balloons, ship bottles, and ice spheres. It’s not a cheap night out by any means but is perfect for those nights when you need to impress someone who isn’t easily impressed, so expect to splurge. If that’s not enough, look into scoring a seat at The Aviary’s basement speakeasy The Office, one of the most exclusive rooms in the city.
Creative cocktails and street food in an upscale “poshtel”
This always-happening hostel bar in the upscale “poshtel” that is the Freehand Chicago has been slinging some of the finest drinks in the city since opening as one of Chicago’s best new bars of 2015. The cool space offers a laid-back house party vibe with vinyl-spinning DJs, exotic cocktails, and street-inspired bar food like fried chicken sandwiches and vegan sausage po’ boys. Try some of their inventive libations like the Potato Chip Old Fashioned or the carrot juice-infused Whatever Happened to Carrot Top while mingling with an always interesting crowd at this second incarnation of the beloved Miami cocktail hotspot, which was twice voted “Best American Hotel Bar” at Tales of the Cocktail in 2015 and 2018.
Enter through the laundromat for live magic and magical cocktails
You wouldn’t expect to find some of the best cocktails in the city in a magic lounge. Then again, Chicago Magic Lounge is full of surprises. Enter through the laundromat of the former 1940s-era commercial laundry facility to discover live magic being performed throughout the unique space, which combines the vibe of an old cabaret theatre with a cool speakeasy-style cocktail bar. Speaking of bars, belly up to the art deco beauty to knock back a series of magical drinks such as the rum-based How Houdini Died and the tequila-infused Abracadabra paired with small plates like potato pancakes or beef and goat cheese sliders. Not only is this bar something different to add to your standard weekend drinking routine, it’s also one of the coolest things you can do in Chicago right now.
One of Chicago’s best rooftop bars is a seductive classic
Rooftop bars are ubiquitous in downtown Chicago. But no rooftop bar pours drinks quite like the A-list cocktails waiting to be discovered at this sexy 18th-floor rooftop emporium above the Raffaello Hotel. Opened in 2012 with a dark speakeasy-styled interior paired with a bright and sunny rooftop patio in the warmer months, Drumbar is worth an elevator ride any time of the year for those in search of limited release whiskeys, scotches, bourbons, and cognacs. Cocktails range from vodka highballs to four types of Old Fashioned to more unusual offerings like the Chocolate Banana Flip made with pisco, sherry, chocolate, banana, whole egg, and sea salt. It’s perfect for a romantically seductive night on the town, and they’ve even got one of the best fireplaces in the city to boot.
Arcade games and craft beer at a good-time Logan Square staple
If you can’t imagine playing Donkey Kong without a Pipeworks Ninja Vs. Unicorn in hand or dominating games of pinball without sipping a Two Brothers Pinball ale, you’re in luck: Chicago offers several excellent options in the arcade bar department. Vintage arcade games and craft beer continue to make the perfect pairing at perennially popular hangouts like Emporium Logan Square, where you can select from 75+ craft beers while taking turns dominating two dozen arcade games including classics like Frogger and Pac-Man in addition to 18 pinball machines, six pool tables, four Skee-Ball lanes, cool wall art, and a generous BYOFood policy in addition to a sometimes-open indoor food truck. There’s also canned cocktails, CBD drinks, rotating pop-ups, and weekend DJs that help keep the large space a nearly mandatory staple of any weekend routine. Since starting the “beercade” trend in Chicago in 2012 with their Wicker Park location, Emporium now maintains three Chicago locations in addition to two out of state in Oakland and Vegas.
A budding craft beer powerhouse makes its mark in Bridgeport
2018 was a breakout year for Bridgeport’s longtime beer overlords Marz Community Brewing, who opened one of the most beloved taprooms of the year in an increasingly taproom-heavy city. What makes Marz special is their attention to detail and diehard community spirit, with the brewery offering a robust lineup of more globally influenced offerings like the Nordic style double IPA Hazestrom and the Belgian white Witbier to pair with their more traditional Chicago-themed 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), Marz’s tap room features 24 draft lines paired with typically atypical eats like Wagyu pastrami and fried bologna served in a beautiful industrial chic, art-heavy space just minutes from Guaranteed Rate Field.
Neighborhood vibes and nudie paintings at an iconic local dive
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 local neighborhood dive has got stiff drinks, a diverse jukebox, an interesting crowd ranging from grizzled old timers to tourists dropping in from nearby Second City, and plenty of stories to tell. The bar is also famous for its wall portraits of everyone from a nude Sarah Palin holding a shotgun to a mid-strip-search Rod Blagojevich painted in the basement studio of the bar by longtime owner Bruce Elliott. Have a few drinks and then go home and listen to their podcast, As the Ale House Turns.
Coffee shop by day, live music venue/beer bar by night
This massive 8,000-square-foot beer bar/music venue/community hangout was opened not too long ago by the crew behind The Whistler and is open all day starting at 11am, when Dark Matter coffee is served and free Wi-Fi laptop working is conducted before the space transforms into one of Chicago’s premier beer bars at night, with live music most nights of the week. 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 a 19% ABV mead called Viking Blod.) With a state-of-the-art sound system and a mostly local lineup of independent musical acts, the 300-capacity music venue makes way to a roomy 150-person year-round patio with picnic tables offering you plenty of time to linger and make new friends.
Chicago cocktail institution still cool after all these years
This Chicago institution has gone through a few iterations over the years, but its most recent revamp continues to be its finest. Left in the sure hands of Brendan Sodikoff’s Hogsalt Hospitality, this red-lit cocktail emporium anchored by a 1937 Brunswick bar is still one of the best places in the city to impress your buddies in town visiting from some other stupid place that isn’t Chicago. Yes they’ve got punches and ice cream drinks, but this is still more of a beer and whiskey shot kind of a joint. Plus live music and burlesque is never a bad thing.
Tiki drinks and Chinese-American food never go out of style
While the tiki trend appears to finally be on a downward trajectory, you’d never know it by stepping into Paul McGee’s cozy Polynesian paradise. The iconic spot remains popular for good reason, as drinking rum-packed delights in volcano bowls continues to be a pretty fun way to spend an evening. The bar gives nods to its tropical heritage with banana leaf wallpaper and thatched bamboo, but doesn’t do so in an overly cheesy way…which is saying something when it comes to tiki bars. Plus, how many tiki joints do you know of that serve late-night Chinese-American eats? The endless accolades continued in 2018, when Lost Lake was named “Best American Cocktail Bar” by Tales of the Cocktail.
It’s all about beer and metal at this no-frills Lincoln Park hang
One of the greatest things to do in winter is drink beer. And one of the greatest places in the world to drink said beer is Chicago. Namely, at places like Lincoln Park’s no-frills dive Local Option, a beer-obsessed oasis of heavy metal drowning in a sea of Prada and poodles. Sample one of their house-branded brews like Kentucky Common while diving into a serious bar menu of out-there eats from swordfish tacos to blue crab quesadillas. And, of course, tater tots.