With its cloud-scraping ceiling and checkered Alice in Wonderland floor, this boutique-hotel bar seems much bigger than it really is. Yet, once you take a peek around, the bar feels quite comfy, and the cocktails here have a similar ability to defy expectations. Sure, you’ll find a nice selection of local spirits and inventive drinks, but the real magic happens when you order a Dealer’s Choice cocktail. You’ll pick a spirit (such as aquavit or mezcal), flavor profile (smoky, spicy, etc.), and glassware (a Collins glass, etc.), and *poof* a unique cocktail made specifically for you appears.
Simply put, Drumbar is stunning. This may lead some to believe that it’s the perfect spot for unfettered Instagramming and throwing back rooftop mimosas like they’re vicious slam dunks. On the contrary, Drumbar makes some of the best cocktails in town, and any visit that includes top-of-the-line seasonal cocktails and an epic lounge sesh in a tufted-leather sofa is really where the action is. Choose from specialty cocktails like the Nouveau Negroni or four types of Old Fashioneds in a sexy speakeasy-styled drinking den on the 18th floor of the Raffaello Hotel.
Years before seemingly every neighborhood on the North Side had its own cocktail joint, the Whistler was drawing crowds to an unexciting stretch of Milwaukee Ave mostly devoid of bars. Fabled mixologist Paul McGee spent three-and-a-half years whipping up drinks here, but the bar is still going strong long after his departure. Patrons keep coming back for the live music and surprisingly affordable drinks, which range from $7 to $12, and seem like a downright steal when compared to some of the pricier options around town. The Whistler helped the craft-cocktail movement bloom in Chicago, but it hasn’t aged one bit. While you’re here, check out the rotating art installations, film screenings, and “movieokie”.
Kick back with a good drink at The Sixth, and you may start spacing out enough to think you’re currently in a Downtown lounge. Yet, the lack of pretension here will quickly snap you back to reality, because for all its spirits-mixing wizardry, The Sixth still has the soul of a buttoned-down neighborhood bar. Knock back cocktails of modern mixology mastery made with specialty ice such as the S’more de Amor dressed with Mexican chocolate and marshmallow foam and the Weston, which contains ingredients such as bourbon, Dark Matter coffee, and pipe tobacco (add a dram of chocolate CBD for extra kick). Both are mesmerizing.
Upon first glance, Milk Room just seems like too much fuss, hidden away in a small section of the Chicago Athletic Association’s second floor. The bar has only eight seats, the drinks cost upwards of $50 each, and in order to visit, customers have to book a reservation through Resy. For the masses, going through all this hassle is, as you can imagine, quite unimaginable. Yet, it’s worth it if you have a taste for the uncommon, because the bar stocks spirits that are, in some cases, not even replaceable. Drinks are made with decades-old bottles that have been acquired at estate sales and such, allowing cocktails to transport patrons back through time. For some, that’s priceless.
For mixologist Paul McGee, the hits seem to keep on coming. Aside from finding success at the Whistler, Three Dots and a Dash, and Milk Room, McGee has sprinkled some of his buzz-baiting pixie dust on Lost Lake. The charming tiki bar provides plenty of colorful drinks, rum bottles, and shareable bowls. But what really stands out, besides the quality of the drinks, is just how much fun everyone is having. Named “Best American Cocktail Bar” by Tales of the Cocktail in 2018, the endlessly name-checked bar also serves late-night Chinese-American eats that pair alarmingly well with cocktails in volcano bowls.
Surely two of the finest cocktail bars in Chicago cannot be located next door to each other, right? Alas, they are, and you should visit them en route to Truth, Meaning, and a great buzz. The Broken Shaker has some serious competition next door at the Berkshire Room. Yet, that has only elevated its game, as evidenced by wonderful cocktails such as the Potato Chip Old Fashioned or the carrot juice-infused Whatever Happened to Carrot Top.
The Aviary is the kind of spot where you’ll always be worried whether you’re underdressed, and the drinks cost about $5 more than you’re used to. Regardless, the cocktails here verge on the fantastical, assaulting the senses with unfamiliar smells, shapes, flavors, and colors. Smoke, booze-filled ice spheres, ship bottles -- the Aviary has been known to serve them all with cocktails and does not give an eff. It’s the cocktail equivalent of seeing Fury Road in 3D: not everyone’s cup of tea, but mind-blowing nonetheless. Drinks are designed as works of art at this high-end cocktail laboratory, and the ethos continues at hyper exclusive basement speakeasy The Office.
The Violet Hour is built on a foundation of confidence. It’s dark, hushed, and does not care for cell phones. Its façade is a mural-covered wall, and the draped interior shrouds the space to such an extent that it’s difficult to tell just how big the lounge is. Hell, the bar even made its own Malört. Yet, the seasonal cocktail menu is dependably impressive, and people still line up to grab a seat during peak times at this Chicago classic. Locate the entrance from the door handle hidden inside the exterior mural on Damen and nerd out on their James Beard Award-winning bar program.
Scofflaw may be one of the best-loved bars in all of Chicago. It has plenty of critical accolades, and loyal patrons swear by this neighborhood spot and its excellent, reasonably priced cocktails. Sure, Scofflaw’s classification as a gin-centric bar is a bit overblown, but that’s because it carries tons of other spirits and prepares them equally as well. But, yes, you should order anything made with their handcrafted Old Tom gin, and stick around until midnight, when the kitchen hands out free fresh-baked cookies, and then sip drinks like the bourbon-based Sea Quake and the mezcal-infused Hearth Tax by the fireplace in their Victorian-style “salon” room.
Armed with a deep library of vintage spirits and a cocktail menu that takes a culinary approach to flavor, Billy Sunday is more than just “another cool Logan Square cocktail bar.” It’s a central gathering place for those in the cocktail know, or curious newbies looking to up their collegiate rum-and-Coke/Red Bull vodka mixology game. Here you’ll find draft cocktails like the Americano, seasonal delights like the whiskey and tea-infused Backhanded Compliment, and vintage classics like the Sazerac and Rusty Nail. There’s also a small but well curated beer list with local offerings from Marz and others, which you may feel free to pair with bar bites like meat boards and sweet potato cakes. Check out the back bar for one of North America’s largest collections or Fernet and Amaro.
This low-key yet fun hang from the folks behind Longman & Eagle, Empty Bottle, Thalia Hall etc. declares itself as “just a bar” -- and the understated sentiment is pretty hard to argue with. The place is just cool without trying too hard, as evidenced by a solid menu of classic cocktails without all the BS and Instagram-obsessed fuss. Order from the selection of their expertly crafted “40 Essentials” cocktail menu with offerings like White Russians, Hurricanes, and Manhattans before checking out some of their obscure brews like Boulder Shake Chocolate Porter and Collective Arts Guava Gose. Finish the night with some bar snacks like their “Moneynugz” house-made chicken nuggets, tater tots, and skewers -- and if you’re still hungry, head next door to sister restaurant Saint Lou’s Assembly for some diner-styled goodness. Be sure to hit up their giant shared back patio in the summer.
One of the most unique drinking destinations in Chicago is this oddball speakeasy with an eye towards the occult located in the basement of the historic Green Door Tavern, one of Chicago’s oldest bars. The place isn’t trying to be a speakeasy, because it was an actual speakeasy during actual Prohibition. The tiny space maxes out at a capacity of 37, but there may be no better date night bar in the city. Once inside, navigate the daily-changing menu of more than 100 cocktails presented on tarot cards as you look forward to strange performances ranging from burlesque to music to pop-up variety acts. The drinks are good, yes, but the environment is even better.
Slippery Slope is well known as one of the rowdiest party spots in the city. But what is less well known is that after you’ve had your fill of late-night drunk dancing, drunk Skee-Ball, and cheap beer at Slippery Slope, you can head upstairs for an entirely different vibe at the ‘70s-styled “fern bar” that is Heavy Feather. We’re not sure what the hell that means, but we are sure the drinks are damn near perfect. Cozy up in a comfy booth where you can actually hear the other person talk and sample a dizzying array of standout libations from the mezcal and tequila-infused Midas Touch to the milkshake-styled Comfy Chair made with cognac, white rum, eggnog, and vanilla ice cream. Don’t worry: They’ll save room for you on the dance floor downstairs.