Nine Bar
Photograph: Marisa Klug-Morataya | Nine Bar
Photograph: Marisa Klug-Morataya

The 50 absolute best bars in Chicago

Raise your shot glass of Malört to the best damn watering holes in Chicago.

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In a city where faded Old Style signs swing outside of beloved dive bars and lines snake around the block at trendy cocktail lounges, the best bars in Chicago act as meeting places, date locales and venues for celebrations. With so many great places to grab a beverage, the list of our all-time favorite bars around town is expansive—and inclusive of taprooms at Chicago breweries, sultry wine bars uncorking bottles of reds and whites, and the finest cocktail bars Chicago has to offer. In a metropolis packed with places to sip and swirl, these watering holes shine extra bright and boozy. Take a look at the best bars in Chicago and find the perfect destination for your next night out.

RECOMMENDED: The best whiskey bars in Chicago

Time Out Market Chicago
  • West Loop

The cozy, all-season crown jewel of Time Out Market Chicago is anchored by a sprawling bar that serves a curated selection of wines, beers and signature cocktails. If the sun is shining, wander outside with a drink to take in skyline views on the breathtaking terrace.

Top bars in Chicago

  • Cocktail bars
  • West Loop
  • price 3 of 4

What is it? A “Japanese dining bar” that serves creative snacks and a cocktail omakase in the West Loop

Why we love it: When a regular ol’ G&T simply won’t do, mixology maven Julia Momose is waiting with splurge-worthy concoctions. Arranged from bright and light to spirituous closers, the drinks here are chock-full of ingredients that reflect Momose’s Japanese heritage, including rice vodka, saké vermouth and umé. The environs are equally intimate, with a bar that offers a peek into the kitchen where chef Noah Sandoval whips up Kusshi oysters, truffle-topped milk bread and other luxurious snacks. Walk-ins are always welcome, but space at Kumiko is limited, so you may want to lock down a reservation before your visit.

Time Out tip: Sake and shochu cocktails and low- or no-proof sips headline Julia Momose’s imaginative menu, but we love asking for a recommendation on sake, which harmonizes beautifully with the refined, umami-rich fare.

Address: 630 W Lake Street

Opening hours: Wed-Sun 6-11:30pm

Expect to pay: $100-$150 per person

  • Lounges
  • West Loop
  • price 3 of 4

What is it? A modern cocktail lounge by The Alinea Group, with a full food menu

Why we love it: When a culinary whiz like Grant Achatz does a cocktail bar, it should go without saying that it's no ordinary cocktail bar. At the Aviary, which opened next door to Next in 2011, cocktails receive the same innovative treatment as the food at Next or Alinea. That is to say, you should expect to drink cocktails like the Junglebird, a science experiment in liquid density, with layers of rum, campari, pineapple-lime syrup and rum "pearls" suspended in the drink. Though the menu descriptions don’t give much away—it’s better that way, trust us—each tipple is constructed to defy gravity and blow minds. You've never seen a drink like it, and given how rare a visit to the Aviary is, you may never again.

Time Out tip: You'll need a reservation (accompanied by a deposit, which is applied to your bill) to enjoy one of the distinct experiences at The Aviary—there are three rotating concepts nightly—so plan ahead!

Address: 955 W Fulton Market

Opening hours: Mon-Thu,Sun 5-11pm; Fri 5pm-1am; Sat 4:30pm-1am

Expect to pay: $150-$200 per person

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  • Cocktail bars
  • Uptown
  • price 2 of 4

What is it? A throwback cocktail lounge and swinging jazz club, with live music seven nights a week

Why we love it: In the 1920s, Al Capone and other nefarious gangsters used to sidle up to this very bar, but these days it’s all about the music (and the satisfyingly stiff, old-school cocktails). Owner Dave Jemilo, who returned the club to its original luster in the 1980s, books smart bebop, swing and free jazz every night of the week local favorites like Andy Brown and Chris Foreman are on regular rotation throughout the year so expect to pay a cover at the door. And in keeping with the unstuffy vibe of the place, the bar’s website warns: “We do not take reservations. We don’t make drinks with egg whites. We don’t make Mojitos. And we take CASH ONLY.”

Time Out tip: A candle-topped table up front puts you at the center of the action, but the plush, emerald-hued booths are the best seats in the house.

Address: 4802 N Broadway

Opening hours: Mon-Fri, Sun 4pm-1am; Sat 2pm-1am

Expect to pay: $20-$30 per person

  • Cocktail bars
  • Wicker Park
  • price 3 of 4

What is it? A James Beard Award-winning drinks den pouring pre-Prohibition libations in the heart of Wicker Park

Why we love it: When it opened in 2007, the Violet Hour was a pioneer of Chicago’s craft-cocktail renaissance, introducing us to well-built classics, house-made syrups and hand-carved ice cubes. Today, the hushed speakeasy still sets the pace, mixing perfect old-fashioneds and Manhattans alongside groundbreaking new concoctions that use only the finest ingredients. The cocktail lounge is exactly what you’d expect from a bar named after a line of T.S. Eliot poetry: pristine (the carefully constructed cocktails are excellent), a tad pretentious (you won’t find a sign on the door—just look for the long lines) and, ultimately, completely and unarguably gorgeous.

Time Out tip: A variety of pre-made cocktails as well as exclusive bottles and cocktail-making kits are available at the bar’s "gift shop," so you can even bring the mixology fun home with you. 

Address: 1520 N Damen Ave

Opening hours: Daily 5pm-12:30am

Expect to pay: $30-$50 per person

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  • Cocktail bars
  • Logan Square
  • price 2 of 4

What is it? A dimly lit cocktail haven offering inventive cocktails and Midwestern hospitality in Logan Square

Why we love it: The team behind Logan Square spots Union and Lardon also operates this intimate and swanky cocktail bar. Housed in the same century-old building as the other two concepts, The Meadowlark provides guests with a cozy den to hang out in—complete with low lighting, comfy leather couches and book-lined shelves. The rotating drinks are all named after childhood activities and there’s also an accompanying menu of small bites. Seating is limited, so get there early to snag a spot.

Time Out tip: The bar food is as nostalgia-inducing as the cocktails: There are Totino's-esque "pizza puffinz" pepped up with pepperoni and tomato jam, a sour cream and onion dip with French onion saltines, and a sweet combo of mini chocolate chip cookies and cereal milk whipped cream that will take you back to your Dunkaroos days. 

Address: 2812 W Palmer St

Opening hours: Daily 5pm-1am

Expect to pay: $30-$50 per person

  • Cocktail bars
  • Humboldt Park
  • price 1 of 4

What is it? A circa-1937 bar with a retro-cool space and old-fashioned cocktails

Why we love it: Following a pandemic-era closure, the glowing red lights at beloved Humboldt Park haunt California Clipper flickered back to life in 2022 thanks to an acquisition by the hospitality company Orbit Group (Good Measure, Segnatore)—and we’re pleased to report that things are back to usual at the bar, from weekly live music to the same red leather booths flanking the walls. Despite the bar’s deliberate “classic Chicago tavern vibe,” the carefully curated cocktail menu is more interesting than a PBR and a shot of Malort.

Time Out tip: If you’re craving a change of pace, venture to the Clipper’s back room (which previously housed coffee shop C.C. Ferns) for DJ sets and late-night dancing meant to channel the spirit of Danny’s, the iconic Bucktown spot that shuttered in 2020. 

Address: 1002 N California Ave

Opening hours: Mon 6pm-midnight; Tue-Thu 6pm-2am; Fri, Sun 4pm-2am; Sat 4pm-3am

Expect to pay: $20-$30 per person

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  • Lounges
  • Logan Square
  • price 2 of 4

What is it? A gin-focused bar from veterans of the Whistler and Boiler Room

Why we love it: Though the hand-drawn menu at this Logan Square gin joint changes with the seasons, every iteration includes a glossary of unfamiliar ingredients, like orgeat (almond syrup with rose/orange water) and baijiu (a pineapple-flavored spirit from China). That humble mentality permeates the space, too—split into two distinct rooms, one more Victorian-style salon with couches and curtains and the other more of a  friendly neighborhood joint with a long barguaranteeing a welcoming, inclusive experience every time. Come with a few friends, settle into a high-backed sofa and take your drinks with an order of shareable snacks, like the thrice-cooked Scofflaw Fries served with garlic aioli.

Time Out tip: The gin bar brings out huge baking sheets of chocolate chip cookies to distribute among guests at precisely midnight, a treat that always pairs well with whatever cocktail you happen to have in your hand.

Address: 3201 W Armitage Ave

Opening hours: Mon-Thu 5pm-1am; Fri 5pm-2am; Sat 11am-2am; Sun 11am-1am

Expect to pay: $30-$50 per person

  • Cocktail bars
  • West Loop

What is it? A secret speakeasy tucked below The Aviary, with classically inspired cocktails and vintage spirits

Why we love it: You won't soon forget an evening at the Office, a tiny, 21-seat speakeasy hidden below lauded cocktail bar the Aviary in the West Loop. There are several prepaid experiences on offer, from an a la carte “The Office Reservation” to a full-blown “The Office Tasting Menu” (pairing classic cocktails, barrel-aged spirits, or rare and vintage selections with “luxury” bites, like foie gras terrines and yolk-crowned beef tartare). But your best bet is to reserve one of four bar stools for “The Office Hour,” a 60-minute guided tasting that includes two bespoke cocktails and food pairings (ideal for pre- or post-dinner tipples).

Time Out tip: Can’t decide on a drink? Opt for the Dealer’s Choice and let the expert bartenders craft a concoction tailored to your preferences.

Address: The Aviary, 955 W Fulton Market

Opening hours: Mon-Thu, Sun 5pm-midnight; Fri 5pm-1am; Sat 4:30pm-1am

Expect to pay: $100-$150 per person

Morgan Olsen
Morgan Olsen
Global Food & Drink Editor
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  • Cocktail bars
  • Armour Square
  • price 2 of 4
  • Recommended

What is it? A self-proclaimed “Asian-ish” cocktail bar inside Chinatown’s Moon Palace Express

Why we love it: Chinatown is home to an incredible assortment of restaurants but until 2022, a cocktail bar was missing from the equation. Nine Bar owners Lily Wang and Joe Briglio have given the neighborhood a drinking oasis with this moody, Blade Runner-esque lounge hidden away in the back of Moon Palace Express. Drop in for Asian-inspired old fashioneds, a classic Mai Tai (enhanced with almond cookie orgeat syrup) and potent concoctions like the Paradise Lost, made with mango brandy, cachaça, ube, pineapple and Thai coconut milk.

Time Out tip: A lineup of Asian-inspired plates and sandwiches complements the cocktails, meaning there's no reason to leave. Order the cold sesame noodles for a spicy bite that doesn’t overwhelm. But no matter what, make sure to get the McKatsu, a fried pork sando packed with flavor.

Address: Moon Palace Express, 216 W Cermak Rd

Opening hours: Mon, Wed, Thu, Sun 5pm-midnight; Fri, Sat 5pm-1am

Expect to pay: $20-$30 per person

Jeffy Mai
Jeffy Mai
Editor, Time Out Chicago
  • Pubs
  • Bridgeport
  • price 2 of 4

What is it? A hybrid liquor store and neighborhood tavern with a large rotating menu of craft beers

Why we love it: Before he founded Marz Community Brewing, Ed Marszewski and his brother Mike remodeled and renamed Kaplan’s Liquors, the Bridgeport bar and liquor store that was owned and operated since 1986 by their mother, Maria. The chandeliers built out of bottles and the 300-plus microbrews are notablenaturally, you'll find some of the latest Marz beers on tap here, served alongside plenty of interesting selections from local and national breweriesbut the real standout feature is the welcoming scene: People like each other here.

Time Out tip: You can grab a bite to eat (and find even more tables) next door at Kimski, which serves Korean-ish fare. You can order a beer at either bar and walk freely between the two venues, though personally, we prefer the cozy, wood-paneled vibes of Maria's. 

Address: 960 W 31st St

Opening hours: Mon 5pm-midnight; Tue, Wed 3pm-midnight; Thu, Fri 3pm-2am; Sat 1pm-2am; Sun 1pm-midnight

Expect to pay: $10-$20 per person

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  • Dive bars
  • Sheffield & DePaul
  • price 2 of 4

What is it? A rock ‘n’ roll booze emporium with an insane whiskey selection and one of the best jukeboxes in town

Why we love it: No Chicagoan’s bar bucket list is complete without a visit to Mike Miller’s no-bullshit establishment, which is known for its extensive collection of whiskey and beer as well as its nightly DJ sets—everything from metal to ska (the good kind) and R&B—and VHS tape screenings. Miller holds court at the three-decade-old bar, which is decorated with red Christmas lights, obscure works from local artists, a well-loved pool table and a pinball machine. If the 1,000-plus options on the whiskey list are too intimidating, don't be afraid to ask the bartender for a recommendation.

Time Out tip: Along with rotating DJs who know their Buzzcocks from their Bullocks, Delilah’s holds a regular line up of special events, including art openings, free movie nights and beer tastings. And don’t miss the Godzilla pinball!

Address: 2771 N Lincoln Ave

Opening hours: Mon-Fri 4pm-2am; Sat 11am-3pm; Sun 11am-2am

Expect to pay: $10-$20 per person

  • Cocktail bars
  • Andersonville
  • price 2 of 4
  • Recommended

What is it? A laid-back lounge with an LGBTQIA+ focus

Why we love it: Be nobody’s darling; / Be an outcast. Named for an Alice Walker poem, Nobody’s Darling made waves when it debuted in 2021 as the second Black-owned LGBTQ+ bar in Chicago, offering an elegant, inclusive space with a high-end cocktail menu to boot. Flip through a selection of riffs on classic cocktails like the fiery Kahlo Margarita (Jon Basil Reposado tequila, passion fruit liqueur, triple sec, lime, agave and spicy bitters) or treat yourself to a drink off the bar’s ever-changing Featured Darlings menu.

Time Out tip: If it's your first time at Nobody's Darling, start off with something like the Carry Me Home Darling, a refreshing gimlet riff that benefits from botanical flavors of St. Germain liqueur. Those looking for something stronger should appreciate the smokey, boozy notes of the bar's Penicillin, which is mixed with a dash of Laphroaig honey. 

Address: 1744 W Balmoral Ave

Opening hours: Tue 5-10pm; Wed, Thu 5-11pm; Fri 4pm-midnight; Sat 2pm-midnight; Sun 2-11pm

Expect to pay: $10-$20 per person

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  • Pubs
  • Logan Square
  • price 1 of 4

What is it? Equal parts casual watering hole and refined cocktail destination, with laid-back digs and an outdoor patio

Why we love it: When brothers Chris and Calvin Marty reopened the old Marble Bar space, we didn’t know what to expect. Since then, the self-proclaimed “fancy cocktail bar” has become a booze-slinging Logan Square institution, complete with balanced drinks and elevated snacks, like calf-liver mousse and port-wine cheese spread. But perhaps Best Intention’s greatest accomplishment has been to find a way to emulate the archetypal Chicago dive bar in all its nitty-gritty splendor. The lived-in space, outfitted in wood paneling and checkered floors, effortlessly looks beyond its years.

Time Out tip: Settle into a table on the big back patio with a group of pals for minty Wondermint Malted shakes and a “baker’s dozen” of griddled cheeseburgers with hand-cut fries and house-made, curry-laced Joppiesaus.

Address: 3281 W Armitage Ave

Opening hours: Tue-Fri 5pm-2am; Sat 11am-3am; Sun 11am-2am

Expect to pay: $10-$20 per person

  • Cocktail bars
  • West Loop
  • price 2 of 4

What is it? A “high-craft, low-key” lounge featuring ingredient-focused cocktails and small plates by Michelin-starred chef Curtis Duffy.

Why we love it: Ever, one of the most luxurious restaurants in Chicago, expanded its footprint in 2022 with the opening of an upscale cocktail bar right next door. Dubbed After, the chic and futuristic-looking lounge provides a new place for Chicagoans to imbibe rare and vintage spirits plus expertly crafted mixed drinks. You’ll have plenty of high-end options to drop your money on, including Japanese whiskies, and scotch and Armagnac flights. And if you’d like some light bites to accompany the drinking, there are premium delicacies like wagyu and toro skewers, too.

Time Out tip: Unlike its fine-dining sibling, reservations aren’t required here—After bills itself as a “come-as-you-are bar” with walk-ins encouraged. (“No dress code, No VIP, No attitude,”  the team promises.) However, if you want to access the concept’s private rooms, The Sound Booth and The B-side, you can do so through Tock

Address: 1338 W Fulton St

Opening hours: Tue-Sat 4pm-midnight

Expect to pay: $100-$150 per person

Jeffy Mai
Jeffy Mai
Editor, Time Out Chicago
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  • Dive bars
  • River West/West Town
  • price 1 of 4

What is it? A true-blue Chicago tavern with tin ceilings, budget beers and a juke filled with Rat-Pack classics

Why we love it: A bistro in France it ain’t, but curiously enough, this tidy, dark dive takes a few traditions from across the Atlantic. The bartender—usually a skinny, older gentleman or at least some variation on the theme—typically dresses in an immaculately crisp white button-down, and you can buy hard-boiled eggs if you need a snack. The larger-than-life posters of De Niro on the wall, however, are completely American. Oh, and smoking is prohibited.

Time Out tip: If you’re an Illinois resident, you can order Richard’s Bar branded liquors (London dry gin, straight bourbon whiskey and the like) online at the venue’s website. You can also pick up bottles directly at the famed establishment, just make sure to have cash if you’re purchasing in person as they don’t accept credit cards at the bar.

Address: 491 N Milwaukee Ave

Opening hours: Mon-Fri 8am-2pm; Sat 9am-3am; Sun noon-2am

Expect to pay: $10-$20 per person

  • Dive bars
  • Ukrainian Village
  • price 2 of 4

What is it? A pretense-free drinks den with a vintage hunting-lodge vibe, an ample patio and a rotating list of spirit-forward cocktails

Why we love it: The neighborhood bar attracts a crowd from far beyond Humboldt Park borders, thanks to a funky, taxidermy-filled interior; large backyard patio with a summer bar and string lights; and cheap beer and shots. The Low Life—a High Life plus a shot of bourbon, Malört, Fernet-Branca or a house-blend of bitters pulled fresh from an amaro machine—is just $7, a lovably steadfast option among the ever-changing list of cocktails. Come summertime, the bar invites Chicago’s top chefs (from notable spots like Maxwells Trading, Nine Bar and more) to host cookouts on the patio every Sunday afternoon. 

Time Out tip: Sportsman’s Club cash only, and you can also bring your own food in, though the Tamale Guy will also likely make an appearance for late-night snacking.

Address:
948 N Western Ave

Opening hours: Daily 5pm-2am

Expect to pay: $10-$20 per person

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  • Cocktail bars
  • Ukrainian Village
  • price 2 of 4

What is it? A ‘70s-inspired lesbian cocktail lounge “for every friend of Dorothy”

Why we love it: Tucked away beneath the former Split-Rail location sits this LGBTQ+ cocktail den that’s decked out in vintage furniture and 1970s-style decor. (A crush-worthy establishment, Dorothy’s fittingly opened on Valentine’s Day 2020.) Through the red door, you’ll find good vibes all around and a rotating selection of intriguing libations, such as the Midnight Margarita, housemade draft margs made with infused charcoal, or the Salad Daze, a herbaceous vodka-based tipple with celery root liqueur, dry vermouth and a Tajin rim. 

Time Out tip: The bar hosts regular events throughout the month but don’t expect your tired old Tuesday trivia nights—the wide-ranging programming includes astrology readings and pop-up tarot events, drag showcases, book clubs, sapphic karaoke, singles mixers and Fruit Salad, Dorothy’s monthly queer open mic.

Address: Split-Rail, 2500 W Chicago Ave

Opening hours: Mon, Wed, Thu, Sun 6-11pm; Tue 5-11pm; Fri, Sat 6pm-1am

Expect to pay: $10-$20 per person

Jeffy Mai
Jeffy Mai
Editor, Time Out Chicago
  • Beer bars
  • Uptown
  • price 2 of 4

What is it? A bar to belly up to with a Belgian brew in hand

Why we love it: A formidable list of craft beers and European imports dominates this sprawling two-story spot with multiple bars. It’s an Andersonville staple, pouring local and international brews, both on draft and in bottles or cans. The bar has special tappings and charity kegs, so be on the lookout as you peruse the 60-plus drafts—if you see a rarity, be sure to snag it. There’s also an encyclopedic bottle list, plus a handful of wines on draft if, for some insane reason, you can’t find anything frothy to fit your fancy.

Time Out tip: Our perfect night involves sampling the drafts at the bar while slurping down the famous ale-steamed mussels, but you could also class it up, grab a proper table and dig into seasonal rotations such as wood-roasted spring chicken with morels and favas, available in the spring.

Address: 5148 N Clark St

Opening hours: Mon-Thu, Sun noon-11pm; Fri, Sat noon-midnight

Expect to pay: $20-$30 per person

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  • Cocktail bars
  • West Loop
  • price 2 of 4

What is it? A straightforward bar serving up simple cocktails, craft beers and “no bullshit” in the West Loop

Why we love it: Though it dubs itself "just a bar," there's way more to Moneygun than meets the eye. Located on the east side of the Kennedy Expressway, this West Loop spot specializes in classic cocktails—30 to be exact. Sip sidecars, cosmopolitans, mojitos, negronis and martinis for $15 each, which is a steal when you consider the bar team is using house-made syrups, sodas and elixirs to craft perfectly balanced sippers. 

Time Out tip: Although the headliner here is the alcohol, they don't skimp on the food offerings with snacks that are more inventive than your usual barroom peanuts: Find goat cheese-stuffed peppadew peppers, chicken wings sauced in hoisin BBQ and taquitos-and-dip combos, from birria with consommé to Chicago-style Italian beef with jus). And if you pop by during Happy Hour, you can get a free order of waffle fries alongside your ten-buck martini.

Address: 660 W Lake St

Opening hours: Tue-Sun 5pm-2am

Expect to pay: $20-$30 per person

  • West Loop

What is it? A stylish bar inside The Hoxton offering craft cocktails and prohibition-chic decor.

Why we love it: This dimly lit, seriously sexy rathskeller beneath the Hoxton hotel is a great bet for those nights when you want to go somewhere where no one knows your name. (Seating is configured in a way that gives each party a sense of privacy, and don’t plan on checking your email or Instagram feed while you’re herethe subterranean space is graciously a black hole for cell service.) The deal is sweetened by a pièce de résistance of a cocktail menu that includes perfected standards. The Negroni, for instance, mimics the flavor of vintage Campari with a top-secret mixture of bitters, achieving an exquisitely balanced, time-traveling tipple. Whether you want something familiar or out of the ordinary, you'll find no shortage of options here.

Time Out tip: There’s not a morsel of food on this boozy bar menu, so plan on grabbing a bite upstairs at Cira or Cabra, the hotel’s two in-house restaurants.

Address: 200 N Green St

Opening hours: Daily 5pm-1am

Expect to pay: $20-$30 per person

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  • Cocktail bars
  • Logan Square
  • price 2 of 4

What is it? A handsome Logan Square pub with high-end but approachable cocktails

Why we love it: Who would have guessed longtime Trotter's chef Matthias Merges would find his calling checking IDs at the door of a Logan Square bar? Granted, his is not just any bar: Here, barkeep Alex Bachman combines his penchant for unusual ingredients (a syrup made from maidenhair ferns, say) with an uncanny sense of balance, turning out creations that both pay homage to and defy tradition —often simultaneously. Most drinks will run you around $15-$18, but the top shelf menu—in which drinks are concocted with vintage spirits, like 1960s Bosford Gin, plus other rarefied ingredients—goes as high as $35 a pop, if you feel like splurging.

Time Out tip: Though Billy Sunday is squarely a bar, the food is a worthy companion to the drinks: Snack on zippy curried nuts, crispy pork chicharrones, loaded potato "cabins” and a top-notch bread service, sided with whipped nduja, cultured butter and onion bacon jam.

Address: 3143 W Logan Blvd

Opening hours: Mon, Tue, Sun 5-11pm; Wed, Thu 5pm-midnight; Fri, Sat 5pm-2am

Expect to pay: $30-$40 per person

  • Cocktail bars
  • Logan Square
  • price 2 of 4

What is it? A bar, gallery and record label featuring creative cocktails and nightly live music with no cover

Why we love it: The Whistler has felt like a mainstay from day one, when it opened in Logan Square nearly twenty years ago in 2008. That’s partly because it embraces the community in a big way. From the outside, the place looks like a gallerywhich, technically, it partially is, with the work of local artists hung in the window. On the inside, it's a tiny lounge, with a permanent stage set up for weekly entertainment. (Local DJs and live bands play most nights.) But behind the bar, the drink-slingers have perfected the art of the cocktail, skillfully crafting colorful refreshments that pack a punch and rotate daily. One sip and there’s no doubt that despite everything else going on here, the drinks are the reason to stick around.

Time Out tip: There are events of interest almost every night, from themed dance parties to the Relax Attack Jazz Series.

Address: 2421 N Milwaukee Ave

Opening hours: Tue, Wed, Sun 6pm-1am; Thu, Fri 6pm-2am; Sat 6pm-3am

Expect to pay: $20-$30 per person

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  • Dive bars
  • Old Town
  • price 1 of 4

What is it? A neighborhood landmark near Second City with a storied past

Why we love it: Knock back stiff drinks with a gloriously diverse cast of characters from grizzled old timers to tourists from nearby Second City at this late-night watering hole, which was established back in 1958. The place is favored by a mix of actors, comedians, neighborhood locals and newspaper guys, from the late Anthony Bourdain to famed Chicago film critic Roger Ebert to actor Michael Shannon. (Fun fact: the latter watched the Oscars here in 2018.) Old Town has had a bit of a tumultuous history over the years (multiple owners, a fire), but it's still a local gem. 

Time Out tip: Those paintings that line the walls were done by current owner Bruce Elliott: along with portraits of famously funny patrons like Stephen Colbert, Bill Murray and John Belushi, don’t miss out on the artist’s more absurd satirical works, including one of Vladimir Putin dancing as a ballerina.

Address: 219 W North Ave

Opening hours: Daily 3pm-4am

Expect to pay: $10-$20 per person

  • Lounges
  • River North
  • price 2 of 4

What is it? A speakeasy underneath Green Door Tavern pouring craft cocktails and offering live entertainment

Why we love it: When we need a break from the city’s repetitive cocktail lounges, we descend into the basement of Green Door Tavern to grab a drink at this secret speakeasy (which, unlike other modern-day bars of the genre, is actually located in an old speakeasy space). Owner Liz Pearce has more than 100 funky cocktails that are described on custom tarot cards. Each night, the team selects a handful of cards from the deck, allowing for a wildly different experience with each visit.

Time Out tip: In terms of actually locating the clandestine spot: Walk through Green Door, head downstairs and enter through the wooden door that’s next to the restrooms. There’s no sign, but if the door guy isn’t there taking names for a waitlist that grows longer as the night goes on, knock and he’ll let you in.

Address: 676-8 N Orleans St

Opening hours: Wed-Fri 5pm-2am; Sat 5pm-3am

Expect to pay: $30-$50 per person

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  • Cocktail bars
  • Lower West Side

What is it? An intimate, 16-seat cocktail bar nestled within Pilsen Yards.

Why we love it: Try searching for “The Alderman Chicago” online and you’ll be lost in a sea of city websites—and maybe that’s intentional. This 16-seat speakeasy-style bar, tucked away in an inky black side room of Pilsen Yards, offers an intimate hideaway for sipping your way through beverage director Lance Bowman’s sophisticated cocktail menu, plus a long list of spirit pours. Creative options worth a try include the jazzed-up whiskey sour “Breaking the Laws” (made with bourbon and rye, spiced guava, black tea, Japanese citrus blend) and the "Whimsy Old Fashioned" (whiskey, smoked tea oleo, truffle maple and s'mores flavor). 

Time Out tip: A word to the wise: Don’t show up without a reservation, especially on the weekends. Due to the size of the venue, The Alderman currently accepts reservations for parties of two to four guests only. 

Address: 1163 W 18th St

Opening hours: Wed, Thu 4:30-10pm; Fri 4-11pm; Sat 3-11pm; Sun 3-9pm

Expect to pay: $20-$30 per person

  • Cocktail bars
  • Portage Park

What is it? A Portage Park bar that serves cocktails amid beautiful houseplants

Why we love it: Sure, plenty of bars are decked out in plants—but how often can you actually buy those plants alongside your old-fashioned or G&T? That’s part of the concept at Moonflower, a Portage Park watering hole draped in lush greenery from nearby Sunnyside Plants, some of which is available for purchase. (As for the plants that aren’t on sale, the team will even find out where you can snag your own locally.) Drinks here have a botanical tilt, too, from the Really Good Martini with chamomile to the fruit-forward No Brainer (rum, strawberry, banana, lime, Angostura), plus a handful of other creative riffs on classic drinks. 

Time Out tip: On weekends, venture downstairs to the speakeasy-style cocktail bar Nightshade, where you’ll find a tight menu that includes—among other treats—a fanciful array of sippers made with fluffy shaved ice.

Address: 4359 N Milwaukee Ave

Opening hours: Tue, Sun 4-11pm; Wed-Fri 4pm-midnight; Sat 10am-midnight

Expect to pay: $30-$50 per person

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  • Albany Park

What is it? A moody cocktail den in Albany Park with retooled classic cocktails and a stylish, relaxed atmosphere

Why we love it: This Albany Park lounge takes its name from a photography term for the dreamy, out-of-focus look achieved by fast-moving lenses, and its interior—all dim lights, sleek furniture and brick walls—offers a similarly sexy aesthetic. Cocktails rotate based on the season, but the core menu favors bold and vegetal spirits; the signature Bokeh cocktail, for example, uses Fernet and cardamom to enliven a traditional sour, while the Camera Obscura (this place loves a good photography reference) consists of mint-infused bourbon and watermelon juice.

Time Out tip: Food-wise, stick to snacky shareables, like fried chickpeas, deviled eggs, olives, and generous meat and cheese boards. And don't miss the glass case at the end of the bar that carries a rotating selection of homemade cookies.

Address: 4716 N Kedzie Ave

Opening hours: Mon-Thu, Sun 5pm-1am; Fri, Sat 5pm-2:30am

Expect to pay: $75-$100 per person

  • Avondale

What is it? A dressed-down remake of the bygone Orbit Room that beckons with snug tavern vibes, spirit-centric sips and nostalgic drunk food that will no doubt keep you drinking.

Why we love it: Flipping a beloved dive is no easy task, but enterprising bar dudes Wade McElroy and Jeff Donahue (Sportsman’s Club, Estereo) nailed it in the old Orbit Room space in Avondale. The bar’s laid-back spirit remains intact, but the forward-thinking menu proffers classic craft cocktails alongside cans of High Life and a reasonably affordable draft beer menu. If you need sustenance, there's usually a pop-up slinging delicious eats out of the kitchen.

Time Out tip: Wind down after a long day at the well-spaced bar, where you’re also guaranteed the fastest service (bar service only here). Come summer, bring a crowd and nab a picnic table in the sprawling back beer garden.

Address: 2959 N California Ave

Opening hours: Mon-Wed 5pm-midnight; Thu 5pm-1am; Fri 5pm-2am; Sat 3pm-2am; Sun 3pm-midnight

Expect to pay: $20-$30 per person

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  • Cocktail bars
  • South Lawndale

What is it? Latin-accented “speakeasy” serving rare tequilas and premium spirits in a storied greystone

Why we love it: Moreno's Liquors has stocked Little Village with shelves upon shelves of tough-to-find tequila and mezcal for more than 40 years. Head to the back of the store, though, and you'll find a neon Chihuahua sign guiding you to Osito's Tap, a tucked-away space that once housed a Bohemian bar (true to the neighborhood's old Czech heritage) and an underground bookie joint. Nowadays, the bar serves a drink and food menu inspired by Little Village's Latinx community, with an especially strong showing of agave cocktails and michelada options, plus a hefty selection of draft beer. Cozy up in high-backed leather booths in the bar’s historic interior or venture outside to the not-so-secret patio for a drink in the sunshine.

Time Out tip: Pad out your belly with a spread of mini chimichangas stuffed with beer-spiked queso, fried chicken wings sauced in habanero buffalo and poblano ranch, and a lamb birria grilled cheese served with a side of consommé for dipping.

Address: 2553 S Ridgeway Ave

Opening hours: Wed, Thu 4pm-1am; Fri 4pm-2am; Sat 2pm-2am; Sun 2pm-midnight

Expect to pay: $20-$30 per person

  • Dive bars
  • Ukrainian Village
  • price 1 of 4

What is it? A beloved dive offering casual drinks, funky vibes, pinball and a photo booth

Why we love it: The bittersweet reality of great little dives is that they often lose charm when overrun by masses of clingers-on. Situated near a stretch of Ukrainian Village that constantly churns out shiny, new bars and restaurants, Rainbo Club has managed to remain an underground favorite and an incorruptible constant since the early 1930s. The L-shaped neon sign beckons from blocks away, pulling patrons into the no-frills environment to down a can of something cheap and a shot of something strong in its coveted red booths, with local artists and musicians awaiting a turn in the photo booth while nodding to everything from Aesop Rock to Black Sabbath.

Time Out tip: That famous photo booth is quick with the camera trigger, so make sure you and your portrait buddies are all settled inside before sliding your dollars into the machine.

Address: 1150 N Damen Ave

Opening hours: Mon-Fri, Sun 4pm-2am; Sat 4pm-3am

Expect to pay: $10-$20 per person

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  • Café bars
  • Logan Square
  • price 2 of 4

What is it? An all-day cafe and agave-forward cocktail bar focused on Latin-American spirits

Why we love it: You might as well be walking into a Wes Anderson film when you enter Estereo, where everything is tinted slightly yellow-gold and patterns—from tiled floors to detailing on the bar—make you feel like you’re on set. The all-day bar from Heisler Hospitality (Pub Royale, Sportsman's Club) has a “leave your worries at the door” vibe that transports you to an island town where three old guys wearing oversized button-downs sit at the bar all day long. And you can sit all day long, too. The bar opens daily at 11am with coffee from Dark Matter and pastries like guava croissants and chocolate croissants, while afternoons offer a cocktail list organized by spirit: pisco, agricole, mezcal, tequila, and so on. The sips highlight fresh juices and syrups of the tropical variety, like tamarind agua fresca and horchata. 

Time Out tip: Come summertime, the garage-door–style windows open up to let in a warm breeze, making Estereo an ideal hangout for imbibing the day away—plus it's dog-friendly!

Address: 2450 N Milwaukee Ave

Opening hours: Mon 5pm-2am; Tue-Sun noon-2am

Expect to pay: $10-$20 per person

  • Cocktail bars
  • River West/West Town
  • price 2 of 4

What is it? An elegant cocktail salon with small bites and regular live music

Why we love it: Boka Restaurant Group co-founder Rob Katz and business partner Matt Ruder transformed the space that once housed Emmit’s Irish Pub into an elegant cocktail lounge. Designed by Kehoe Designs, The Pearl Club is sophisticated yet cozy, sporting floor-to-ceiling velvet drapes, rich wooden tones, a restored grand bar and other artful touches. You'll imbibe unique riffs on classic libations, like a clarified ube colada and an herby gimlet splashed with house celery vinegar.

Time Out tip: When you need a snack, the kitchen turns out Asian-accented bites like kombu salt chips, smashed cucumber salad and beet-cured kingfish with ponzu and blood orange, but our fave is the karaage-style, twice-fried chicken nuggets (with your choice of classic buffalo, Caesar dry rub, maple gochujang or jalapeño and fish sauce marmalade).

Address: 495 N Milwaukee Ave

Opening hours: Mon-Wed, Sun 5pm-midnight; Thu 5pm-1am; Fri, Sat 5pm-2am

Expect to pay: $30-$50 per person

Jeffy Mai
Jeffy Mai
Editor, Time Out Chicago
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  • Beer bars
  • Bucktown
  • price 1 of 4

What is it? A map-lined tavern for travel lovers, touting more than 200 global beers, including hard-to-find imported Belgian suds on tap

Why we love it: If the cartography, colorful flags and copious copies of National Geographic didn’t tip you off, this Bucktown bar honors wanderlust, and it has a beer list to match. If you’re a more low-key drinker but like the vibe, stop by in the a.m. when the Map Room functions as a coffeehouse, serving lattes and cortados. But, come sunset, the regulars hunker down to travel the world through suds, hopping from Chicago to Germany to Quebec. Stop in on a weekday to enjoy discounts on beer from various regions of the world. 

Time Out tip: Stop in on a weekday to enjoy discounts on beer from various regions of the world. On occasional Tuesdays, the bar unveils new or limited releases of specialty beers.

Address: 1949 N Hoyne Ave

Opening hours: Mon-Fri 7:30am-2am; Sat 8am-2am; Sun 11am-2am

Expect to pay: $10-$20 per person

  • Cocktail bars
  • West Loop
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What is it? A 1960s Parisian-inspired cocktail bar in the Fulton Market neighborhood

Why we love it: Although it's one of the newest additions to the Fulton Market strip, Bisous has already proven itself to be a local favorite and heavy hitter. The Parisian-themed cocktail bar transports you to the swanky days of yesteryear, with libations to match. There's an entire subsection of drinks paying homage to the classic martini, but respectable signatures like the saffron-based almost RICH & almost FAMOUS and Agricole Daiquiri are rave-worthy as well. 

Time Out tip: The snack menu is quite modest in both scope and portion size—expect stuff like marinated olives and aged Manchego, tinned seafood served with kettle chips and Tabasco, pork rillettes with cherry-dijon mustard and seeded crackers, and house-made chocolate bonbons for something sweetso make sure to grab some grub before heading over to Bisous for the perfect nightcap. 

Address: 938 W Fulton Market

Opening hours: Mon-Thu 4pm-2am; Fri 3pm-2am; Sat 3pm-3am; Sun 3pm-midnight

Expect to pay: $30-$50 per person

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  • Avondale

What is it? A spacious, bi-level bar with ample draft beer and progressive live programming

Why we love it: Part bar, part music venue, Sleeping Village has a little something for everyone in Avondale. With 56 beer and cider drafts, the bar is the main attraction; guests can choose from lagers, IPAs, stouts and sour beers from around the world that are all listed on a menu that's projected onto one of the venue's walls. However, the gigantic beer selection and spacious digs are only half of the equation at Sleeping Village—there's also a 300-capacity music venue tucked into the back of the building where you'll find a dynamic lineup of intimate and cheap (sometimes free) shows from local acts and touring bands, with the occasional comedy gig tossed in for good measure.

Time Out tip: Don't skip the adjacent patio, which is typically packed with folks enjoying cold drinks when Chicago's weather cooperates.

Address: 3734 W Belmont Ave

Opening hours: Mon-Wed, Sun 6pm-1am; Thu, Fri 6pm-2am; Sat 6pm-3am

Expect to pay: $10 to $20 per person

  • Bucktown
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What is it? A trendy Bucktown cocktail bar serving an extensive coffee menu during the day, a thoughtful cocktail program at night and relaxed vibes throughout.

Why we love it: A newbie to the Bucktown bar scene, Truce is a coffee shop by day and cocktail bar by night. The walk-in only establishment aims to embody the spirit of a neighborhood bar, with an elevated drink menu to keep patrons coming back. There’s even an entire section devoted to coffee-splashed cocktails, from espresso martinis pepped up with orange and salted demerara — one of the best versions of the caffeinated classic in the whole city — to a Spent Latte Punch, made with clarified latte, silver rum and Thai banana. 


Time Out tip: The cocktail list changes regularly — however, you can't go wrong with the striking Absinthe Frappe, featuring fluffy pandan whip. And the chai daiquiri and lemon pound cake martini are just as intriguing.

Address: 1935 N Damen Ave

Opening hours: Mon, Thu-Sun 8am-1am; Tue, Wed 8am-3pm

Expect to pay: $20-$30 per person

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  • Cocktail bars
  • Ukrainian Village
  • price 2 of 4

What is it? A maritime-inspired neighborhood tavern in Wicker Park

Why we love it: Named in honor of building owner and former bar maven Mary Kafka, Queen Mary Tavern is a self-proclaimed time capsule that introduces modern-day imbibers to the old-time drinking traditions of sailors. The low-key feel is reminiscent of the chill vibe at Sportsman’s Club (another Heisler bar). The maritime theme is restrained, with ship, mermaid and sea captain artwork scattered around. However, the steady drink list here, rather than offerings that change daily, means that the cocktails are more ambitious and consistent. 

Time Out tip: Set down an anchor and stay for a glass or two of the Daily Grog, a rotating punch that's garnished with fresh citrus and just enough spice to thaw your weary bones. In the mood to get wild? Order a Miller High Life with a shot of dark rum for just $6.

Address: 2125 W Division St

Opening hours: Mon-Thu 5pm-1am; Fri-Sun 3pm-1am

Expect to pay: $20-$30 per person

  • Shopping
  • Liquor stores
  • Avondale
  • price 2 of 4

What is it? Craft beer shop with a diverse selection of hard-to-find brews, plus daily tastings

Why we love it: True to its name, The Beer Temple is a sanctuary for craft-brew lovers, complete with a spacious taproom where visitors can have a drink and a bottle shop stocked with plenty of interesting brews. Kegs from local, national and international breweries regularly join the menu at the bar (and are sometimes depleted in the course of any evening), so you're likely to find at least a few new selections every time you visit. Not a fan of the latest double IPAs and barrel-aged pastry stouts? Don't worry, this place has cans of Hamm's and shots of Malört, too.

Time Out tip: Owner (and Certified Cicerone) Chris Quinn is quick with a quality recommendation, interesting tidbits on particular brewing processes, encyclopedic knowledge of the history of various brews and samples of new beers on his doorstep.

Address: 3173 N Elston Ave

Opening hours: Mon-Thu 11am-midnight; Fri, Sat 11am-1am; Sun 11am-10pm

Expect to pay: $20-$30 per person

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  • Contemporary American
  • Loop
  • price 3 of 4

What is it? A stylish rooftop bar and restaurant atop the Chicago Athletic Association Hotel

Why we love it: Whenever we want to impress out-of-towners, we book a table at the Chicago Athletic Association Hotel’s 13th-floor rooftop bar, from which Millennium Park, Lake Michigan and the city skyline are on glorious display under a glass atrium. The drink lineup complements the vistas with easy-sipping selections that are best enjoyed in the sun—like Trouble Will Find Me, made with tequila, mezcal, watermelon, and yuzu soda. As a bonus, the spirit-free menu rocks, offering bold, wildly creative quaffs.

Time Out tip: The food spread is also mostly well-executed and comes in massive portions that are made for sharing. Gather your buds and order a feast of curried carrots with duck-skin crumble, Beau Soleil oysters with pickled shallots, smoked whitefish dip with grilled sourdough and green-curry prawns with chorizo and ginger.

Address: Chicago Athletic Association, 12 S Michigan Ave

Opening hours: Mon-Thu 11am-11pm; Fri 11am-midnight; Sat 10am-midnight; Sun 1am-11pm

Expect to pay: $30-$50 per person

  • Cocktail bars
  • Lower West Side
  • price 2 of 4

What is it? Hidden basement bar serving up both creative and classic punches

Why we love it: Below Dusek’s Board & Beer, this ‘70s-themed punch-focused bar decorated with a fish tank, wood paneling and a huge fish on the wall —think of it as a deluxe version of your grandparents’ basement. Like its name suggests, punch is the main draw here: The eight options, divided into “contemporary” and “classic” categories, are pre-made and then dispensed into single glasses, carafes (for up to four people) or group-friendly punch bowls (for up to eight). The milk punches are beloved for good reason, with a satisfying mix of rum, coconut and chai tea.

Time Out tip: Warning: The drinks are boozy, so you’re practically required to get something to eat. Thankfully, the late-night grub is downright delicious—the plantain tacos, crab-rangoon empanadas, Mexican Caesar salad, carne asada fries and the rest are courtesy of Mariscos San Pedro upstairs. (The food menu is available Fridays and Saturdays from 10pm to 1am.)

Address: Thalia Hall, 1227 W 18th St

Opening hours: Mon-Thu 5pm-1am; Fri, Sat 5pm-2am; Sun 5pm-midnight

Expect to pay: $30-$50 per person

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  • Dive bars
  • Lower West Side
  • price 1 of 4

What is it? A cash-only Pilsen bar with craft beer, live music and some of the best tater tots in town

Why we love it: This speakeasy-esque space—a vacuous room, lined with booths and sprinkled with tables and chairs—has been a nightly respite for local artists for more than two decades in East Pilsen. The mac and cheese and tater tots (which you can get loaded Sloppy Joe-style during weekend brunch, topped with nacho cheese, pickled onions and giardiniera) are greasy must-haves, and you should wash ’em down with $6 draft beers from the likes of Dovetail, Maplewood and Off Color. 

Time Out tip: There’s free live shows like surf jazz on the first Sunday of every month—along with Friday-night fish fries, regular barbecue brunches, supper clubs, urinal-themed celebrations, etc—and don’t miss the photo booth tucked in the back corner.

Address: 2149 S Halsted S

Opening hours: Mon-Thu 4pm-2am; Fri 3pm-2am; Sat noon-3am; Sun 11am-2am

Expect to pay: $10-$20 per person

  • Cocktail bars
  • River West/West Town

What is it? Cocktail lounge with pouring classic and modern variations in an eclectic, art-filled space.

Why we love it: This jewel-toned, cocktail-focused River West hangout favors a chic-yet-accessible approach to drinking, with a menu that riffs on classic drinks alongside a respectable selection of beer and wine. Unlike some of the flashier cocktail bars on our list, drinks here are elegant but unfussy, consisting of a mostly-pronounceable list of ingredients (like the Get Figgy With It, made with single whiskey malt and fig). 

Time Out tip: The indoor space—all navy walls adorned with eye-catching artwork—is on the smaller side, but a sprawling outdoor beer garden offers room to stretch your legs. Come summer, nab a seat at the expansive patio studded with trees, flowers and punchy murals, where you’ll often find live music on the weekends. In winter, fire pits and outdoor heaters warm up that cold Chicago chill. 

Address: 694 N Milwaukee Ave

Opening hours: Mon-Thu 3pm-midnight; Fri 3pm-2am; Sat noon-3am; Sun noon-midnight

Expect to pay: $20-$30 per person

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  • Cocktail bars
  • River North
  • price 2 of 4

What is it? A tropical cocktail destination with rums and house daiquiris in a retro Polynesian-style setting

Why we love it: You'll find the not-so-secret entrance to this subterranean tiki bar in an alley east of Clark Street, between Hubbard and Illinois streets. Once your eyes have adjusted to the dark interior, you'll notice the colorful drinks parading around the room: The cocktails here are served in tiki glassware and accented with fresh flowers, colorful straws and skewers of fruit. (Similarly, those smoking punches are proffered by bar staff bedecked in long Hawaiian dresses and Jimmy Buffet-esque shirts.) Nudge your way to the crowded bar to try classics like the Painkiller, with Caribbean rum, tangerine, pineapple and coconut—it goes down a little too easy after a long day.

Time Out tip: The tiki cups are available for sale, but if you don’t want to shell out $60 for some kitschy glassware, pocket the swizzle sticks, which are shaped like mermaids, octopi or McGee’s bespectacled tiki head. 

Address: Salesforce Innovation Center,  435 N Clark St

Opening hours: Mon-Wed, Sun 4pm-midnight; Thu, Fri 4pm-1am; Sat 2pm-1am

Expect to pay: $30-$50 per person

  • Avondale

What is it? A Neighborhood bar serving cocktails and bar bites in Avondale

Why we love it: Mother’s Ruin arrives in Avondale by way of New York City (with an additional satellite location in Nashville), bringing its signature spiked slushies and craft cocktails to a spacious storefront on Milwaukee Avenue open 365 days a year. Drink names on the rotating cocktail menu offer an irreverent touch—recent entrants range from Viagra Triangle to Brat Summer to Betty White Bathroom—and pack a boozy punch that’s well-matched against the joint’s genuinely unmissable selection of bar snacks, including one of the best burgers in Chicago. 

Time Out tip: Sidle up to a high-top table beginning at 11am daily, when the bar starts slinging hearty brunch mains, for daytime cocktails and a breakfast burrito with your choice of chorizo or ’shroom base. (Note: All food and beverages can be ordered directly from your favorite bartenders, as table service is not available.)

Address: 2943 N Milwaukee Ave

Opening hours: Mon-Fri, Sun 11am-3am; Sat 11am-2am

Expect to pay: $20-$30 per person

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  • Hotel bars
  • Wicker Park
  • price 2 of 4

What is it? Intimate lounge atop the Robey hotel with chic cocktails and sweeping views

Why we love it: Situated on the 13th floor of Wicker Park’s Robey hotel, the Up Room is a cocktail lounge with quite a view of the distant Chicago skyline. The intimate indoor seating is limited, but try to grab a coveted section inside the Robey spire on the outdoor rooftop. While the spirit list is sure to excite whiskey aficionados, the innovative, seasonal cocktail menu still has something for every palate.  Try the Coyote, a powerfully smoky blend of Ardbeg Scotch and grapefruit bitters, named after the tower in which the hotel resides. If sweet is more your style, order a Kid Koala or a Sweet Boys Only—the drinks are built around eucalyptus and pineapple, respectively.

Time Out tip: Be prepared for a wait—the lounge only seats 35 people—but when you get to the front of the queue, also be prepared to be blown away.

Address: The Robey, 2018 W North Ave

Opening hours: Mon-Thu, Sun 5pm-midnight; Fri, Sat 5pm-1am

Expect to pay: $20-$30 per person

  • Cocktail bars
  • River West/West Town
  • price 2 of 4

What is it? A hip corner bar in a vintage building serving premium cocktails in a famously narrow space

Why we love it: The Matchbox has been a fixture on the corner of Ogden and Milwaukee Avenues for more than 85 years, acquiring a new life—and a much cleaner look—when Chicago restaurateur David Gevercer took over the space in 1995 and started serving classic cocktails at a cheap price. The drink list hasn’t changed in years and every single one  tastes like a classic cocktail should, replete with a healthy dose of booze. The margaritas and gimlets are still the draw: smooth, delicious and sweet (glasses are rimmed with powdered sugar).

Time Out tip: If the thought of being crammed in this tiny boxcar of a bar makes you nervous, relax. The patio practically doubles the capacity of the place, and it’s the perfect spot to throw back one of its margaritas. We’re also fans of the house-infused vodkas and the grub from the adjacent dining car (literally), Silver Palm.

Address: 770 N Milwaukee Ave

Opening hours: Daily 3pm-2am

Expect to pay: $10-$20 per person

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  • Breweries
  • Irving Park

What is it? Chicago's women-owned brewery and cider house, offering New American comfort food and growlers to grow

Why we love it: There are just a few cideries located in Chicago, but Eris Brewery and Cider House is easily the most beautiful of the bunch, housed in a retrofitted church that dates back more than a century. Snag a seat at a sleek booth in the two-level space (or outdoors on a parking lot patio) and sample some of the house ciders, which range from crisp, dry selection to sweeter options blended with cherry or cranberry juice. The kitchen serves a formidable menu of pub grub, including fried cheese curds, burgers topped with bacon jam and birria grilled cheese. And if you're not a fan of cider, Eris brews beer, too!

Time Out tip: Make sure to try the award-winning Foiken Haze IPA if it's on tap.

Address:
4240 W Irving Park Rd

Opening hours: Mon-Thu 4-10pm; Fri noon-11pm; Sat 11am-11pm; Sun 11am-9pm

Expect to pay: $20-$30 per person

  • American creative
  • River West/West Town
  • price 1 of 4

What is it? A restaurant, natural wine shop and cheese counter in Chicago's Ukrainian Village

Why we love it: Whether you're looking for a special bottle of wine to take to a dinner party or you're hankering for a loaded charcuterie board, this all-day cafe and bottle shop has you covered. The menu at All Together Now sources market-fresh produce from Midwestern farms and utilizes smoked and cured meats from Underground Meats in Madison, Wisconsin. Stop by at brunch time for coffee and egg sandwiches (plus bagels on the weekend), during the afternoon for hearty sammies and small plates, or plan a post-work outing for pillowy ricotta dumplings and ruby-red grilled hanger steak.

Time Out tip: Don’t leave without perusing the miniature grocery and bottle shop, which is stocked with splurge-y kitchen treasures—think tinned fish, homemade granola and hunks of funky cheeses—and a lean-yet-sophisticated selection of wine.

Address: 2119 W Chicago Ave

Opening hours: Tue-Fri 11am-9pm; Sat 10am-9pm; Sun 10am-5pm

Expect to pay: $30-$50 per person

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  • Wine bars
  • Logan Square

What is it? An eclectic wine bar and bottle shop with a popular patio in Logan Square

Why we love it: Late-night spot East Room closed back in 2019, but co-owner Zack Eastman (Dorian's) resurrected the space as a bar and bottle shop with a sprawling back patio where you can sip pét-nats and rosé beneath shade canopies by the Blue Line. Appropriately named Easy Does It, the storefront is a casual, laid-back shop where folks can stock up on natural wines, local beers and liquor. And when the temperatures drop, the drinking moves indoors to a second floor bar with open seating and plenty of room for events like wine tastings and DJ sets.

Time Out tip: A monthly membership club makes it easy to discover a slew of wines you've probably never heard of, each of which are marked with fun, approachable tasting notes.

Address: 2354 N Milwaukee Ave

Opening hours: Mon-Wed 5pm-midnight; Thu 5pm-1am; Fri 5pm-2am; Sat 2pm-2am; Sun 2pm-midnight

Expect to pay: $20-$30 per person

  • Pubs
  • South Shore
  • price 2 of 4

What is it? One of Chicago’s oldest and most-beloved gay bars

Why we love it: This Black-owned gay bar has been holding it down in Chicago’s South Shore since the 1960s. On past visits, we watched the crowd groove to hip-hop and house while also chatting and canoodling on the sidelines. Swing by on the weekends for DJ nights and lively dance parties that go until the early hours of the morning, pumping everything from Top 40 pop to classic disco to house music. And for a glimpse at who could be the next RuPaul, pony up the cover for amateur drag shows that the beloved LGBTQ venue hosts several nights a week.

Time Out tip: The entry process can be rather rigorous (we had to be buzzed in and then patted down), but it’s worth it for the still-cheap and strong drinks and a friendly vibe.

Address: 7041 S Jeffery Blvd

Opening hours: Wed 6pm-4am; Thu 9:30pm-4am; Fri 8pm-4am; Sat 8pm-5am; Sun noon-4am

Expect to pay: $10-$20 per person

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