With an abundance of speakeasies and secret drinking dens, Chicago's cocktail culture is as lively as ever. But now tipplers can look forward to exploring Tiki joints, throwback lounges, and rooftop respites that are adding something different to the scene. These new watering holes are pushing all the limits with cutting-edge cocktails and cool perks. Here’s our guide to the new wave of Chicago's creative cocktail spots and, for good measure, some not quite brand-new spots that have refreshed their offerings with new drinks and concepts.
Lost Lake
Studious rum drinks with elaborate fruit garnishes and an ornate, exotic décor draw crowds to this tropical gem located near the hip environs of Logan Square. And while the name Lost Lake implies a hidden find, it seems this Tiki bar has officially popped up on the radar of every determined cocktail aficionado in the city—on a recent night, a line of eager imbibers formed out the door. But the wait is worth it: Envisioned by beverage-world wiz Paul McGee (formerly of Three Dots and a Dash), Lost Lake is the epitome of Tiki chic with its banana-leaf-print wallpaper and nautical knickknacks. Drinking with a group? Order the Tortuga, a shareable scorpion-type bowl brimming with aged and overproof Guyana rums, sweet Vermouth, Curaçao, pomegranate, cacao, and citrus juices (it serves four). Don’t miss Chinese take-out at your seat or barstool; it’s available from Thank You, conveniently located next door.
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The Rec Room
Only open Thursday through Sunday nights, the Rec Room feels like a trip straight back to the 1970s. Located downstairs at Henry’s, the intimate space in River North garnering attention for its house-carbonated bottled cocktails; the Feel the Beat is made with white rum, blackstrap rum, Dark Matter coffee, blueberries, and lime. The drink menu also offers up canned beer and large-format punches served off of a cart, plus the groovy space is outfitted with comfy leather couches, a glittery disco ball, and a retro analog juke box. This is the type of place to hang out with friends old and new; there are plenty of games to keep bar goers occupied, such as Ms. Pac-Man, Connect 4, and checkers. Best of all, patrons can raid the fridge at midnight; it’s stocked with a rotating assortment of drunk food, like pizza, fried chicken, and pie.
The Drifter
Strange vintage cartoons projected on a curtain, live contortionists, and craft cocktails: welcome to the wild world of The Drifter, an eccentric, 37-seat space located in a former speakeasy in the basement of The Green Door Tavern, also in River North. The drink menu changes nightly, and you’ll find descriptions of the tipples printed on tarot cards; when it gets busy, patrons sometimes just hand over the cards of the drinks they desire to the bar keeps. To go with the periodic performances—which have included burlesque performers, magicians and musicians—imagine conversation-starting cocktails, like the Malort-based Essential Monsters, named after an art piece containing freak-show pictures from the early 1900s.
I|O at The Godfrey Hotel
With Riley Huddleston (formerly of The Aviary) at the helm of this clubby, inside/outside rooftop bar, imbibers can expect avant-garde, chef-focused cocktails that often have fifteen ingredients or more. Try the Chef’s Margarita: it includes some eighteen components, including tequila, vanilla reduction, lemon-mint drinking vinegar, and lime topped with a nuanced habanero-salt foam. Proving that molecular gastronomy is not just for show, each margarita is pH-checked to ensure the perfect balance of sweet and tart. Consider I|O at The Godfrey Hotel a great pick for when the mercury starts to dip: you can huddle around its two-level fire pit with a clever cocktail from the new fall drink menu in hand while taking in stunning views of the Chicago skyline (a retractable roof ensures you’ll stay warm regardless of the temperature).
Cindy’s
Perched on the thirteenth floor of the recently opened Chicago Athletic Association (a boutique hotel), Cindy’s serves up jaw-dropping views of Millennium Park and Lake Michigan, along with an inventive drink program and light, local bites from its rooftop restaurant and open-air terrace. The look evokes a breezy Great Lakes summer house, with twinkling string lights, picnic-style communal seating, and plenty of green touches. The drink list is curated by “spirit guide” Nandini Khaund—please, don’t call her a mixologist—and ranges from large-format bottles to craft cocktails. Don’t miss the creamy (yet vegan) We’ll Always Have Paris, made with Aviation gin, cocchi Americano, fresh strawberries, house-made pistachio milk, and date syrup for a Moroccan feel. Other creative drink options include a throwback Apothecary Service ($20), which claims cures for what ails you with creations from behind the bar, plus a streamlined menu of tisanes (herbal teas) and mocktails for non-drinkers.
River Roast
Boasting water and city views from nearly every table, River Roast, located on the Chicago River, has earned a reputation for its contemporary Midwestern tavern fare dreamed up by James Beard Award-winning chef Tony Mantuano and executive chef John Hogan. But don’t go just to dine: The beverage program delivers plenty of surprises, including a farmer’s market punch on draft; cold-brewed cocktails; and and new drinks tweaked for fall palates, created from two slow drip-infusion towers; not to mention plenty of local and regional beers. Must-try tipples include the Unicorn Tears (“Peket Genever, Amaro, and magic”) and The Hemingway’s Muse (mint-and-lime-infused rum with demerara and club soda).