The 29 absolute best bars in Chicago

Transport yourself to a tropical paradise at Logan Square darling Lost Lake. Helmed by Paul McGee and Shelby Allison, the tiny tiki bar has reached institution status in record time. How? By going beyond banana dolphins and bendy straws (though there are also plenty of those!) and pushing the boundaries on what rum mixed with fruit juice can taste like. With every new year and each new menu, we continue to be blown away by Lost Lake’s talented team, dangerously delicious drinks and Asian-inspired bar snacks.

When it comes to dining or drinking at an Alinea Group property, expect the unimaginable—and then some. Surprising presentations and executions characterize the cocktail list at the Aviary in West Loop. A layered Jungle Bird boasts rum-soaked jelly balls that burst in your mouth; a Manhattan is enclosed inside a giant globe of ice; and a sherry-bourbon sipper is served inside a plastic bag infused with the aroma of fresh oatmeal cookies.

This hip 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), pretentious (you won’t find a sign on the door—just look for the long lines) and, ultimately, completely and unarguably gorgeous. Pro tip: Stop by for the bar's absinthe happy hour Monday through Thursday from 6 to 8pm, when you can sample pours of the spirit and cocktails that incorporate it for discounted prices.

Hidden inside Fat Rice in Logan Square, the Ladies' Room is one of the most ambitious cocktail program in Chicago. The elixirs here are inspired by global flavors and showcase funky ingredients like avocado leaf tincture, salted coconut foam, pancake cordial and lemongrass shochu. If you're with a group, consider upgrading to one of the large-format options, like the Burning Bird, a tropical combination of rum, aperol, palm sugar, amarao, calamansi and pineapple.

Gin cocktails are the specialty at Scofflaw, a sexy lounge in Logan Square that's in the same bar family as Slippery Slope, the Heavy Feather and the Moonlighter. Though the drink offerings change with the season, guests can always expect to sit down to a beautiful hand-drawn menu (complete with a glossary of hard-to-pronounce ingredients). As an added bonus, the food here outshines most bar snacks by miles.

This neighborhood bar attracts folks from far beyond Humboldt Park borders thanks to a funky, taxidermy-filled interior, a sprawling backyard patio and excellent drinks. The lowlife—a shot of whiskey or a pull from the amaro machine plus a High Life—is just $5. Come summertime, the crew behind the bar welcomes Chicago's top chefs to host cookouts on the patio; $20 gets you a plate of food and one drink.

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, made with fresh lemon and lime juice, top-shelf liquors and powdered sugar, and poured with a heavy hand. We’re also fans of the house-infused vodkas and the grub from the adjacent dining car (literally), Silver Palm.

A formidable list of craft beers 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 (we found Almanac Beer Co.’s Ginger Gose the last time we stopped in). There’s also an encyclopedic bottle list, plus eight wines on draft if, for some insane reason, you can’t find anything frothy to fit your fancy.

Al Capone and other gangsters used to hang here in the 1920s, but these days it’s all about the music. Owner Dave Jemilo, who returned the club to its original luster in the 1980s, books smart bebop and free jazz with a discriminating ear. Local favorites Frank Catalano and Patricia Barber both maintain residencies throughout the year. Come early, as it’s usually understandably busy.

What this tiny bar lacks in size, it makes up for in personality. Situated on the mezzanine level of Soho House Chicago, Fox Bar is a cozy late-night watering hole with a focus on vinyl and no-nonsense bartending. (And no, you don't have to be a member to check it out.) Between the entrance and the bottle-lined bar, you'll find oversized chairs along the walls and a long communal table in the middle of the room. The menu here is always changing, but look out for seasonal ingredients and playful spirits, like brown butter-washed cognac and rhubarb-infused aperol. The prices are right and the service is unparalleled, making Fox Bar a loveable neighborhood favorite. 

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 traditional tiki glassware and accented with fresh flowers, colorful straws and skewers of fruit. 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.

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. 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.

This mysterious Logan Square booze den stands in stark contrast to Chicago’s plethora of bright, Instagram-friendly bars. Guests enter the room through an alley and descend a staircase to find the 40-seat interior. The jolting focal point of the dimly lit bar is a neon sign that reads Weddings & Funerals. Put away your phone and order from a menu of lesser-known classic cocktails as you sink into the sultry space.

The Whistler felt like a mainstay from day one. That’s partly because it embraces the community in a big way: You'll find the work of local artists in the window, and local DJs and bands play most nights. The ever-changing cocktail list might include the spice-filled Angostura Sour this week and a refreshing Mexican Summer—with tequila, lime and jalapeño—next. Plus, there are events of interest every night, from the LGBT-friendly Slo ’Mo party to the Relax Attack Jazz Series. It’s always a killer night at the Whistler.

Enterprising barchitects Wade McElroy and Jeff Donahue (Sportsman’s Club, Estereo) took another shot at reviving the beloved Orbit Room space in Avondale—this time with much success. Ludlow Liquors carves out a distinct identity for itself through a roster of spirit-forward cocktails available by the ounce plus greasy drinking food that artfully blends Midwestern nostalgia with Filipino tradition.

Part bar, part music venue, Sleeping Village has a little something for everyone. With 56 beer and cider drafts, the Avondale bar is the main attraction: Guests can choose from ales, stouts, barleys and fruit-centric brews from around the world. The doors open daily at 11am, and patrons can start the day with drip coffee, a pour-over or nitro cold brew from Dark Matter Coffee. 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.

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 the wildly talented crew turns out creations that both pay homage to and defy tradition—often simultaneously. Though Billy Sunday is squarely a bar, the food is a worthy companion to the drinks—think cheesy monkey bread, baked oysters and duck rillette.

The novella-length menu at this cozy, low-key Humboldt Park alcove contains loving and helpful descriptions of an impressive selection of wines and beers. But if you still have no idea where to start, ask—everyone behind the bar is willing to let you taste through options until you find a wine you’ll love. The list includes lots of gems, most for less than $10 a glass, and the majority of bottles are under $100. To fuel all the wine-drinking, the food menu includes an array of small plates served until 1am.

This long, wooden bar is helmed by a few middle-aged women who, on Sundays, mix huge batches of kamikazes and sell them for $2 a pop—but the real draw here is karaoke. If you get there and the door’s locked, don’t get discouraged. Just ring the bell over and over again (sometimes the bartenders can’t hear it over yet another version of “Don’t Stop Believin’”).

Ed Marszewski—editor-publisher of Lumpen, festival host, gallerist and general Chicago indie-art-world guy-around-town—and his brother, Mike, remodeled and renamed Kaplan’s Liquors, the Bridgeport bar that was owned and operated since 1986 by their mother, Maria. The chandeliers built out of bottles and the 300-plus microbrews are notable, but the real standout feature is the welcoming scene: People like each other here. You can grab a bite to eat (and find even more tables) next door at Kimski, which serves Polish-Korean fusion dishes.

When brothers Chris and Calvin Marty bought the old Marble Bar space and reopened it as Best Intentions a few years back, no one knew what to expect. Since then, the “fancy cocktail bar” has become a booze-slinging institution in Logan Square, complete with balanced drinks and upgraded bar snacks. But perhaps Best Intention’s greatest accomplishment was finding a way to emulate the great Chicago dive bar in a way that doesn’t feel forced. The lived-in space, outfitted in wood paneling and checkered floors, effortlessly looks beyond its years.

This West Loop tavern flaunts a very average-sounding tagline: "It's just a bar." The truth is, of course, it's way more than that. The menu, which is blazoned on the mirrored wall of the bar, boasts 31 classics, like the Last Word, a Sidecar and even a Cosmopolitan. Each is crafted with superior ingredients and hand-crafted syrups and tinctures. The hip-hop music soundtrack doesn't hurt either.

There’s something extra special about a bar that embodies the spirit of Chicago, and this year we celebrate the punk-rock spirit of Delilah’s. You’ll find slasher flicks on the TVs, $1 beers, pool tables and alt-country–DJ nights at Mike Miller’s no-bullshit bar. Delilah’s frequent whiskey and craft-beer tasting events bring Miller out from behind the bar, making the Lincoln Park hang feel like home (though, no, you can’t sleep there). Ultimately, the friendly dive is more than just a place to have a drink; it’s helped shape Chicago’s bar scene into what it is today.

Logan Square corner tavern Spilt Milk entered Chicago’s bar scene seamlessly, carving out a distinct identity in a neighborhood that has no shortage of quality watering holes. Nico Osteria vet Matty Eggleston opened the place in 2016, offering a thoughtful beer list, a gorgeous wooden bar and—most importantly—a carefully curated cocktail menu with drinks like a refreshing Concord grape julep. 

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. It’s a favorite of many cultural icons, from the late Anthony Bourdain and actor Michael Shannon (he watched the Oscars here in 2018) to Chicago film critic Roger Ebert—and should be a fave of yours, too.

The rooftop restaurant and bar at the Chicago Athletic Association Hotel offers some of the best views of the city, with an expansive look at Millennium Park and the Lake. At $16, the drinks here aren't cheap, but they're beautifully balanced and photo-ready. Also noteworthy is the lounge's spirit-free menu, a roster of boozeless beverages like the Balenciaga, with spiced clementine, pineapple, fresno, lemon and ginger beer.

Situated near a stretch of Wicker Park that constantly churns out shiny new bars and restaurants, Rainbo Club is an incorruptible constant. The red neon sign beckons from blocks away, pulling patrons into its no-frills, no-bullshit space to down a shot and a can of something cheap in its coveted red booths.