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Hopleaf

United States

Hopleaf Bar

This list of the best bars in Chicago blends classics that define the city's drinks scene with everything new and hot right now.

Lost Lake

Bars are like children (so we’re told)—it’s impossible to love one more than the other. But if we had to pick just a few of the best in this famously bar-heavy city right now, the cool kids below would clearly make the cut. From low-key neighborhood dives and romantic date spots to top-notch beer bars and fancy dens of highbrow mixology, here are the best bars in Chicago to hit this winter. Drink up, Chicago.

Bars are like children (so we’re told)—it’s impossible to love one more than the other. But if we had to pick just a few of the best in this famously bar-heavy city right now, the cool kids below would clearly make the cut. From low-key neighborhood dives and romantic date spots to top-notch beer bars and fancy dens of highbrow mixology, here are the best bars in Chicago to hit this winter. Drink up, Chicago.

One of Chicago’s most successful bars of recent years went dark for a long 18 months during the pandemic, but has since re-emerged in all its glory with some notable changes. For one, they no longer serve “tiki” drinks—the drinks are now deemed “tropical” (i.e. more traditional and less ostentatious, with less cultural appropriation, to boot). Also, the food menu has been completely reimagined with everything from Braised Pork Shank to Fried Icelandic Cod. You can also sign up for their “Lost Lake at Home” subscription boxes if you don’t feel like schlepping to this tropical oasis in the snow. How to book: Reserve via&nbsp;<a href="https://resy.com/cities/chi/lost-lake?date=2021-11-09&amp;seats=2" target="_blank">Resy</a>.

Another one of Chicago’s top cocktail bars has also just recently re-emerged from a long pandemic hibernation, a welcome development for fans of this&nbsp;<a href="https://www.thrillist.com/drink/chicago/hipster-chicago-bars" target="_blank">top hipster bar</a>. Live music has also made a return to the stage, along with a new ever-changing cocktail menu made up of classics and Whistler originals. In case that wasn’t cool enough, the walls are now adorned with monthly rotating art installations from local artists, which you can peruse while contemplatively stroking your straggly winter beard with a cocktail in hand. How to book: Stop by for first come, first served seating.

The Whistler

The folks behind AliveOne, Easy Bar, The Owl, and Estelle’s, (AKA Four Entertainment Group), have done it again with this spanking new neighborhood bar near the corner of Central Park and Milwaukee. The years-in-the-making concept brings an old-school flavor to the 1940s-era building with an 80-year-old wooden bar and vinyl green barstools along with a backyard-styled outdoor space. And yes, you can still get 4EG’s famous half-priced&nbsp;<a href="https://www.thrillist.com/drink/chicago/best-happy-hours-in-chicago-neighborhoods" target="_blank">happy hour specials</a> every weekday—easily one of the best deals in the city. As an added bonus—or liability, depending on how you look at it—Jello Shots and&nbsp;<a href="https://www.thrillist.com/drink/chicago/malort-liquor-facts" target="_blank">Malort</a> + Old Style combos are always on hand. How to book: Stop by for first come, first served seating.

Photo by Ryan Gac

Central Park Bar

Rejoice—Uptown has a new arcade bar. The long-running trend refuses to die, and instead is making its way north with this unapologetically fun space located just across from the Morse Red Line stop. Packed with nostalgic games and a space theme, the bar is something of a neighborhood comeback from the owner of the now-defunct Uptown Arcade, which closed last year. There’s also regular events, from VHS movie nights to pop-up markets, so grab a barstool (or post up at your favorite pinball machine) and get cozy. How to book: Stop by for first come, first served seating.

Mission Control Arcade Bar

Life can get tough. Times can get dark. But the Hideout is reopened, so all's finally right with the world. Following a long pandemic closure and a time spent as an outdoors-only venue, The Hideout is now welcoming back patrons into what is easily one of Chicago’s most truly magical spaces. Live music and other oddball events (competitive reading anyone?) have also made their return to the&nbsp;<a href="https://www.thrillist.com/eat/chicago/chicago-bars-and-restaurants-with-bizarre-backstories" target="_blank">beloved 1890s-era dive</a>, so stop wasting any more time dilly-dallying with other bars and head straight towards that beckoning Old Style sign. How to book: Stop by for first come, first served seating or reserve performance tickets <a href="https://hideoutchicago.com/" target="_blank">online</a>.

Hideout Inn

The Hideout

All respect to the&nbsp;<a href="https://www.thrillist.com/drink/chicago/best-breweries-in-chicago" target="_blank">Revolutions and the Half Acres</a> of the world, but sometimes you gotta give the little guy his due. And, in this case, that little guy is this laid-back hangout located just off the newly expanded North Branch Riverwalk. Nothing too fancy. Nothing too gimmicky. Just a standout assortment of beers and a chill, unpretentious space to sip some of Chicago’s most under-the-radar craft beer gems with a few friends while watching the Bears game. The outdoor patio overlooking Horner Park is also a great place to catch live bands, but that’ll have to wait until the spring—hey, consider it something to look forward to. How to book: Stop by for first come, first served seating.

Burning Bush Brewery

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 (while wishing for warmer days), seasonal standbys like the gin-based Fisticuffs, or “Billy Beloveds” like the Billy Sunday Old Fashioned. This is drinking as drinking was meant to be. How to book: Reserve via&nbsp;<a href="https://www.exploretock.com/billysunday" target="_blank">Tock</a>.

Billy Sunday

Billy Goat Tavern

This good-time emporium 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 Half Acre. How to book: Reserve via <a href="https://www.opentable.com/r/broken-shaker-chicago" target="_blank">OpenTable</a>.

Broken Shaker at Freehand Chicago

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 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.

The Victor Bar

Victor Bar

The Victor Cocktail Bar

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 tacos and Mexican snacks. More importantly, they’ve got a clear winner on their hands. How to book: Reserve via&nbsp;<a href="https://www.ositostap.com/reservations-safety" target="_blank">OpenTable</a>.

Osito's Tap

Osito’s Tap

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 bask in the recently opened bar-within-the-bar <a href="https://www.thrillist.com/drink/chicago/best-chicago-speakeasies" target="_blank">The Alderman</a>, an intimate 18-seat cocktail lounge with drinks curated by award-winning mixologist Lance Bowman. How to book: Reserve via <a href="https://www.pilsenyards.com/reservations" target="_blank">OpenTable</a>.

Pilsen Yards

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 be good. 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 whiskey-packed Swizzle 34 or daily punch specials in addition to a hearty offering of craft brews and spirits. How to book: Reserve via <a href="https://resy.com/cities/chi/scofflaw?date=2021-08-05" target="_blank">Resy</a>.

Scofflaw

Long known as one of the&nbsp;<a href="https://www.thrillist.com/drink/chicago/best-beer-bars-in-chicago" target="_blank">best beer bars in Chicago</a>, 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.

It may be the <a href="https://www.thrillist.com/drink/chicago/best-chicago-speakeasies" target="_blank">least secret “secret bar” in Chicago</a>, 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 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 <a href="http://www.theviolethour.com/the-violet-hour-subscription-series" target="_blank">globe-trotting three-month cocktail subscriptions</a>, so you’ll never have to wait long for the perfect tipple. How to book: Reserve via <a href="https://www.exploretock.com/theviolethour/experience/196754/the-violet-hour-standard-reservation-indoor-seating" target="_blank">Tock</a>.

The Violet Hour

One of <a href="https://www.thrillist.com/drink/chicago/oldest-bars-in-chicago" target="_blank">Chicago’s oldest bars</a>, this 1907 original served as notorious gangster <a href="https://www.thrillist.com/drink/chicago/8-chicago-bars-with-notorious-mob-connections" target="_blank">Al Capone’s favorite Prohibition-era hangout</a>. These days, Green Mill remains one of the <a href="https://www.thrillist.com/drink/chicago/the-best-bars-with-live-music-in-chicago" target="_blank">top jazz clubs</a> in the country as well as a damn fine spot to grab a drink. The cinematic vibes of this <a href="https://www.thrillist.com/drink/chicago/places-to-drink-in-chicago-bar-bucket-list" target="_blank">bucket list-worthy bar</a> 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. Just don’t be too loud while the bands are playing or you will be unceremoniously shushed. Drinks are nothing too fancy or gimmicky, just strong and delicious. How to book: Stop by for first come, first served seating.

Green Mill Cocktail Lounge

Green Mill

This erstwhile Bridgeport establishment is well known as one of <a href="https://www.thrillist.com/drink/chicago/best-chicago-slashies-taprooms-packaged-good-stores-liquor-store-bars" target="_blank">Chicago’s premier “slashies”</a> (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 <a href="https://www.thrillist.com/drink/chicago/best-beer-bars-in-chicago" target="_blank">best beer bars in the city</a> as well as a leading <a href="https://www.thrillist.com/travel/chicago/exploring-south-side-chicago" target="_blank">South Side institution</a>). Yet their cocktailing game is no slouch either, with offerings including the to-go Maria’s Luau Party Pack. How to book: Stop by for first come, first served seating.

Maria's Packaged Goods & Community Bar

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 <a href="https://www.thrillist.com/drink/chicago/best-beer-bars-in-chicago" target="_blank">most interesting beer selections in town</a>. 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.

The Map Room Chicago

The Map Room

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 whimsical ventures like boozy slushies, much ink has been spilled in <a href="https://www.thrillist.com/recipe/three-dots-and-a-dash" target="_blank">this fair publication</a> 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. How to book: Reserve via <a href="https://www.exploretock.com/threedotsandadash/" target="_blank">Tock</a>.

Three Dots and a Dash

Expect the unexpected at this high-end cocktail laboratory from world-renowned chef <a href="https://www.thrillist.com/eat/chicago/chicagos-best-celebrity-chef-restaurants-rick-bayless-stephanie-izard-grant-achatz-and-more" target="_blank">Grant Achatz</a>, 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 <a href="https://www.exploretock.com/theaviary" target="_blank">Tock</a>.

The Aviary

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 <a href="https://www.thrillist.com/drink/chicago/chicago-brewpubs-craft-beer" target="_blank">increasingly taproom-heavy city</a>. 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 <a href="https://www.community-bar.com/" target="_blank">Maria’s Packaged Goods</a> and <a href="https://www.kimskichicago.com/" target="_blank">Kimski</a> (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 <a href="https://www.lifeonmarz.club/" target="_blank">Life on Marz Community Club</a> in Bucktown.) How to book: Reserve via <a href="https://www.exploretock.com/marz-community-brewing" target="_blank">Tock</a>.

Marz Community Brewing

Marz Community Brewery

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 <a href="https://www.thrillist.com/lifestyle/chicago/the-most-legendary-moments-in-second-city-history" target="_blank">Bill Murray</a> 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 <a href="https://www.thrillist.com/drink/chicago/no-shots-allowed-an-oral-history-of-the-old-town-ale-house" target="_blank">plenty of stories to tell</a>. 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.

Goya60 / Flickr 

Old Town Ale House

This massive 8,000-square-foot bar-music venue-community hangout entered the scene not too long ago courtesy of the crew behind <a href="https://www.thrillist.com/drink/chicago/hipster-chicago-bars" target="_blank">The Whistler</a> and quickly evolved into one of <a href="https://www.thrillist.com/drink/chicago/best-beer-bars-in-chicago" target="_blank">Chicago’s top beer bars</a>. 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.

Sleeping Village

<a href="https://www.thrillist.com/authors/jay-gentile">Jay Gentile</a> is an award-winning freelance journalist specializing in travel, food &amp; 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 <a href="https://twitter.com/thejaygentile">@thejaygentile</a>.

Beverage Director

Beverage Director: Find the Best Bars to Drink at in Your City

Drink

Bars

Where to Grab a Drink in Chicago Right Now

Best Bars in Chicago to Drink at Right Now

Cocktail legends Lost Lake and The Whistler return while an ambitious arcade bar enters the ring. 

Bars are like children (so we’re told)—it’s impossible to love one more than the other.

Hopleaf Bar

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Where to Grab a Drink in Chicago Right Now

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