If you’re looking for an inventive drink, the best cocktail bars in Chicago, Illinois will never disappoint. There’s a lot in the city to choose from, whether you want to drink atop a hospital (we’re serious), visit an authentic tiki lounge, gently sip from a mixed beverage as you get a manicure, or indulge in cabaret within a speakeasy. You can spend most of your waking hours wetting your whistle in the Windy City, and we encourage you to explore of Chicago as much as you can. However, if it seems overwhelming, SELECT has narrowed down the list to several of Chicago, IL’s best cocktail bars to help get you started in your travels.
| Name | Location | Description |
| Bordel | 1721 W Division St | With everything from a concoction called an Oaxacan Streetfight to artfully-prepared Old Fashioneds and a Prom Queen (it’s got Greek yogurt in it and strawberry) to pick from, the menu alone here will be enough to grab your attention. Beyond the booze though, Bordel’s theme nights, including Speakeasy Wednesdays, Vaudeville Thursdays, and cabaret Fridays will provide enough adult enjoyment to last until the following week. DJs serve up music on weekends, and the kitchen also will set you up with tapas and other clubby food offerings. |
| Beauty Bar | 1444 W Chicago Ave | Get a mani with a martini (or a margarita) in this cool chain concept bar. The place is kitted out in retro décor with beauty salon chairs/fixtures (think vinyl, chrome, mirrors, and classic lady-silhouettes with ’dos), although the glowing panel of booze behind the counter tells you they’re ready to serve you a heady adult beverage, or 20. Hit the jam-packed, colorful dance floor under the glitter ball, or just come for the special “Salonathon” nights. Happy hour deals are a draw, and covers are usually cheap, so crowds often line up outside en masse. |
| Lost Lake | 3154 W
Diversey Ave |
It’s no small accomplishment that in a city of supremely frigid winter weather that this bar sets out to and succeeds in warming you up by recalling the heyday of tiki. Cocktails here have earned high marks citywide, and deservedly so: Paul McGee and his “Tiki Team” serve things up pitch-perfectly in coconut or pineapple cups, funky-faced glasses and conch-style containers. They also have a nice daily drinker of their own called Lost Lake Exotica Ale, just in a bottle. The joint is authentic, so be sure that your tropical shirt is on point. |
| The Aviary | 955 W Fulton Market | This lounge in Fulton Market sits across the way from Next, providing a really choice, slow cocktail experience. Décor is minimal on purpose, perhaps to showcase the quality of the mix. Prices here are not on the low side, however. But that’s all right, because when tasty spherical Elderflower ice cubes arrive in your glass (or you watch your drink as it’s strained through some weird alembic that results in a smooth, boozily strong liquid leaving a delightful tail trailing down your throat), you’ll know precisely where your money went. |
| Billy Sunday | 3143 W Logan Blvd | This quaint gastropub in Logan Square is elegantly minimalist, with a hammered tin ceiling and lacquered wooden tables and bar. The fixtures give off an easy, lambent glow, and the cocktails are mixed well, with yummy presentations backed by yummy flavor. Food is mostly small plates, with some larger offerings as well, perhaps the heartiest being Curried Farmers Pie or an old-world fave, Galumpkis. Billy Sunday also has Sunday Service classes instructing you in the history/art of making and serving (and drinking) cocktails at 1PM. |
| The Library at Gilt Bar | 230 W Kinzie St | The Library in the downstairs at Gilt Bar (which is itself a decent dining/drinking spot) features plummy surroundings in which to enjoy mixology done very well indeed. A not-so-hidden gem in River North, The Library features built-in shelving stacked with gilt volumes, creating a rich, intelligent feel. Plunk yourself into a curved Chesterfield and try a classic American cocktail; you can even order food from the same menu as upstairs while avoiding most of the restaurant rush. Here, its ambient, dim lighting makes it especially good for a date night. |
| Maude’s Liquor Bar | 840 W Randolph St | Cool, convivial, chic and smooth, with exposed painted brickwork and overstuffed sofas, Maude’s makes all things all right. While the food is French-inspired, including classic Parisian fare such as escargot and mussels, the wine list is deep, and the drinks – i.e. Death in the Afternoon and some shaken stars such as a Lion’s Tail and French Gimlet, along with a nice Sazerac and Boulevardier – do double duty on the fizz and spirits side. Ambiance here is vintage, modern and somehow earthy all at once, so really sink into it. |
| California Clipper | 1002 N California Ave | The old-timey, retro vibe in here is authentic Chicagoland, as the California Clipper has been in this (renovated) space since the late 1930s. The deep cocktail list skews toward the traditional, and that fits in just right with the vinyl booths and chrome stools. There’s live music and the atmosphere is fun. There’s a charming, colorful menu that will have you ordering up bourbon, scotch, whiskeys and gin, most likely, and not second-guessing the heavy pour that you receive. |
| The Whistler | 2421 N Milwaukee Ave | At the Whistler, cocktails seem to change every day, as the staff seemingly can do no wrong when mixing up drinks. Every night, the entertainment switches up with live acts (think soul, jazz, R&B and more) and warms up the fairly timbery environs. Like so many Chicago bars, the hammered-tin ceiling is proof of authenticity, as is the laid-back vibe: You can relax and enjoy yourself, as they take your enjoyment pretty damn seriously. |
| Annex | 259 E Erie St, 18th Fl | This Streeterville spot features a huge outdoor terrace with breathtaking views. The fact that it and its sister space, Green River, sit atop a hospital just adds to the interest. The upscale corner bar features crafted seasonal cocktails to match the sleek-as-hell atmosphere. You can build your drinks from recipe cards that derive from the base spirits and seasonal ingredients on offer. |
CHEAT SHEET:
To learn more about the best cocktail bars in Chicago, Ilinois, also tune in to:
David Podgurski has written about travel, books, fashion + entertainment for digital and print media. He’s hunted down vintage finds in crumbling attics, published poetry, worked for the New York MTA, and likes to haunt museums, cafés and shops. When he isn’t traveling or writing, he’s thinking about his next trip — and what to enjoy when he gets there.
| M | T | W | T | F | S | S |
|---|---|---|---|---|---|---|
Leave a Reply