The Best Bars in Chicago

It makes sense that tough-guy Chicago would have its fair share of breweries and old-guy boilermaker bars, but it’s gained a reputation as a cocktail town, too, with inventive bartenders and glamorous lounges that invite lingering. Order up your drink of choice at one of our favorites.

564 W Randolph St, Chicago, IL 60661, USA
West Loop denizens can get their fill of locally made spirits at this distillery and cocktail bar, where cofounder and head distiller Tremaine Atkinson bottles up just about everything of an ABV nature—with a bespoke spin. Its vodka may be its flagship offering, but it’s proved its aptitude with a handful of other liquors as well, from gin and rum to amaro and limoncello. If you can’t make one of its Tuesday or Saturday tours, swing by anyway for a dram; a full cocktail list pairs up with bites throughout the week and features go-tos like the Cease & Desist, a melding of CH London Dry Gin, Lapsang souchong, ginger, honey, and lemon.
1520 North Damen Avenue
The first rule of the speakeasy is that it can’t be easy to find. The Violet Hour’s door is directly across the street from Big Star. Look for the handle on the wall and the light above it, because the door mural changes frequently and cleverly disguises the space. It doesn’t take reservations, so expect to wait in line as the number of people in the bar at any time is also tightly controlled. This is good, because it won’t ever be packed! The Violet Hour isn’t a get-up-and-mingle kind of joint, which makes it the perfect dark, sexy lounge for romantic dates and quiet conversations about world domination. The cocktail menu changes frequently, so even if you’ve been before, you should go again. (And try the Finocchio Focaccia.)
3201 West Armitage Avenue
Scofflaw breaks all the craft-cocktail-bar rules by serving strong, affordable drinks that arrive quickly with no snooty attitude. There’s even street parking, something anyone driving in Chicago will appreciate. I’m not sure what else you could want for a night out, but here are a few more reasons to drop by: 1. Gin. There are more kinds here than you’ve probably ever seen—small-batch, big brands, high-end, even the bar’s own Old Tom gin. If it’s made with juniper, then Scofflaw has it, and knows how to mix it. 2. Chocolate chip cookies baked at midnight. Why aren’t you there already? 3. Wide recognition as a top-notch watering hole. Be sure to get there early and stake out a space.
2548 N Halsted St, Chicago, IL 60614, USA
Playing live blues music until 4am every night of the week, featuring all of Chicago’s talented local musicians and now newly renovated to take up 3 storefronts on Halstead, Kingston Mines is one of Chicago’s best bars. Go for the 3 Bs: Barbq, Beer and Blues. And bring a big crowd because there’s lots of room.
737 W Randolph St, Chicago, IL 60661, USA
A visit to Chicago‘s historic meat-packing district at any time is, in and of itself, a bit of an adventure. The area has certainly seen enough transitions to bring in the hip and happening in recent years. However the best reason to visit, outside of the odd chop factory still in operation, is the Haymarket. This is beer and food done right. From the Mother Jones Abbey Style Dubbel to the Last Chance Belgian I.P.A., these are beers of distinction. Toss in the best soft pretzels in the Midwest, the famed chocolate stout cake—with bacon—and a brilliant casual atmosphere, and you’ve got a good place to go for a drink.
678 N Orleans St, Chicago, IL 60654, USA
After the great fire of Chicago, but before the new ordinance was passed saying no more wooden commercial structures, the building that is now the Green Door Tavern was erected. That was waaaaay back in 1872, and the place is still alive and kickin’. The name comes from Prohibition times, when establishments that turned a blind eye to the ban had green doors, so as to designate their unsavory (or savory rather) practices. The building even sports a bit of “lean” to it, due to its age. (If you partake in the Prohibition-era drinks, you’ll also have a bit of lean upon departure.) In today’s world of spotless countertops and mood lighting, the Green Door Tavern is nothing but the bare bones of the city’s history. The food is good old-fashioned pub fare, and the drinks are beer and cocktails. Various events, from live music to costume parties, celebrate the time of gangsters and the like. So, while some may eschew going to a simple bar, know that this place is steeped in history and lore. If only the walls could talk...
More from AFAR
Sign up for our newsletter
Join more than a million of the world’s best travelers. Subscribe to the Daily Wander newsletter.
AFAR Journeys
Journeys: Europe
Journeys: Europe
Journeys: Europe
Journeys: Europe
Journeys: United States
Journeys: Sports + Adventure