There’s a line in Carl Sandburg’s seminal 1914 poem “Chicago” that fits the city’s modern drinking scene. It’s not so much a line as it is three words: stormy, husky, brawling. The trio of descriptors fits because Chicago is a brilliant hard-drinking city populated by industry folks and consumers who proudly uphold its burly, working-class Big Shoulders ethos, even as it continues to curate a well-deserved reputation for acclaimed excellence in the drinks space. For the traveler who sets their sights on a getaway to the Windy City, experiencing this dichotomy by enjoying a thoughtful glass of wine or beer, indulging in a killer cocktail, or braving a slug of Jeppson’s Malort provides the clearest path to connecting with the city’s true soul.
Chicago’s bar scene provides residents plenty of opportunities — both permanent and temporary — to forge this link. As the following eclectic batch of venues demonstrates, there is some variance to approaching this special synergy, but that simply allows folks to experience Chicago’s Upper Midwest big-city magic in ways that can fit whatever their sensibilities happen to be at any given time.
Here are nine of the best places to drink in Chicago.
Best Place to Start Off a Big Night: Longman & Eagle
The cardinal rule to any proper bar crawl is to make sure not to embark on an empty stomach. However, there are occasions when kicking off a night of liquid exploration can dovetail quite nicely with an excellent meal. This Logan Square venue meets such a moment with a solid rotation of cocktails, a deep roster of brown spirits, and a culinary program boasting multiple years of Michelin-star love. The venue’s elegant yet rustic style hearkens back to the days when inns dotted Chicago neighborhoods, a vibe further extended by the half-dozen rooms offered for overnight stays above the bar. Classics abound on the menu, either in traditional or riff form — its “improved” Gimlet, for instance, features aromatised tonic wine quinquina for extra oomph. If you’re seeking a cozier crawl kickoff, adjourn to the venue’s back patio-adjacent Off Site Bar, a tiny garage-themed offshoot with fewer than 20 seats.
Tip Jar: Logan Square is built for bar crawls. The artsy West Chicago neighborhood is home to several spots boasting Tales of the Cocktail recognition. During the crawl, take a moment to raise a glass in remembrance to Tales’ 2018 American Bar of the Year, Lost Lake, which shuttered in early 2021.
Address: 2657 N. Kedzie Ave., Chicago, Illinois, 60647
Best Place to Get Your Groove On: The Whistler
Music and cocktails equally fuel the spirit of this award-winning Logan Square spot. Imbibers can expect a good balance between classics, riffs, and funky progressive beverages like the It’s My Party, a tart, creamy concoction featuring Old Tom gin, amaro, and liquid cheesecake. The venue’s music stage welcomes an eclectic pastiche of jazz, electronica, rock, and other genres throughout the week. Weekends, on the other hand, are made for dancing, and a rotation of DJs spin everything from disco to dubstep to get toes tapping and hips shaking. Regardless of what’s being played or spun, the music helps build a palpable energy that evolves depending on what time you arrive. “If you get here early, it’s a quiet place with craft cocktails,” explains head bartender Alex Barbatsis. “If you get here late, it’s a loud place with craft cocktails. If you get here really late, it’s all about tequila shots and $3 PBRs.”
Address: 2421 N. Milwaukee Ave., Chicago, Illinois, 60647
Best Place to Hide from the Weather: Three Dots and a Dash
Chicago’s occasionally brutal weather makes escapism necessary. This self-described “tiki speakeasy,” tucked away in an alley in Chicago’s River North neighborhood, provides easy, casual shelter from the city’s meteorological shenanigans — particularly when sitting at the space’s elongated thatched hut-style bar top. Classic tiki drinks pepper the menu, including the cocktail inspiring the venue’s name. They’re joined by an array of modern tropical beverages featuring house-made modifiers and ingredients sourced from the global regions inspiring their creation. Group drinks come in whimsically cool vessels and can be massive — its 15-year Appleton Estate rum and yellow Chartreuse Port Royale serves six to eight willing participants. Be forewarned: The drinks marked by skulls on the menu pack a wallop. Adventurous types can also pop into the venue’s bar-within-a-bar, The Bamboo Room, and partake in a guided encounter focusing on rhum agricole.
Tip Jar: Three Dots and a Dash is tough to find, and some locals have become good at spotting people struggling to locate the entrance. They’ll gladly guide you to the front door — for a small fee.
Address: 435 N. Clark St., Chicago, Illinois, 60654
Best Place for Spirits Exploration: Billy Sunday
It’s easy to go down a rabbit hole once you get into a spirit. Amaro offers a particularly deep plunge, and there’s no better spot in Chicago to explore the bitter digestif than this critically acclaimed Logan Square spot. Named after a Chicago baseball player-turned-evangelist and temperance advocate, the venue is equally adept at guiding guests through its enormous amaro collection, regardless of their level of knowledge. “Some guests join us just to dive deep into the back bar, and others have never tasted amaro before, so we cater to each guest accordingly,” explains Billy Sunday beverage director Stephanie Andrews. “My favorite thing to do is to pour a taste of something typically in the cocktail they are enjoying and extend the conversation from there!” Plenty of amaro-free cocktails also spark chatter, most notably a collection of “top-shelf” drinks featuring rare and vintage spirits.
Address: 3143 W. Logan Blvd., Chicago, Illinois, 60647
Best Place for a Shot of Malort: CH Distillery
Shooting Malort is a rite of passage in Chicago — not necessarily a good one, but one nonetheless. According to Barbatsis, the best way to experience this odd imbibing tradition is by visiting the distillery that produces this aggressively bitter digestif. The bar menu at the distillery’s on-site tasting room embraces this perceived reputation for nasty flavor, referring to the juice as an “anti-hero” as it beckons guests to try a shot. The potential for taste bud torment isn’t the sole reason to come to this West Loop spot. Once you’ve earned your Chicago stripes (or talked the most gullible person in your entourage to sacrifice their palate), stick around and explore the distillery’s other expressions such as its award-winning vodka, rum, American-style gin, and amaro, either on their own or in a cocktail. Be sure to come hungry: The tasting room is also home to Jinsei Motto, a chef-driven sushi restaurant that’s evolved from pop-up to permanent fixture.
Address: 564 W. Randolph St., Chicago, Illinois, 60661
Best Place for a First Date: Webster’s Wine Bar
When considering a wine bar for a first date, no level of light dimness or cozy intimacy will make up for a lousy wine list. This Logan Square space, which receives ringing endorsements from Barbatsis and Andrews, has both elements down cold. Indeed, the space’s snug design yields a vibe that’s appropriately conducive to first-date flirtation. Yet it closes the deal through a carefully curated list of exclusively minimal-intervention and natural wines from around the globe. While it’s been a natural wine bar since 1994 — a date that makes it the oldest such wine bar in Chicago — a wine’s natural status isn’t the final arbiter or whether or not it’s considered for inclusion on Webster’s list. “We take a Marie Kondo approach to our wine list,” explains general manager and wine director Chris Schneider. “If a wine doesn’t bring us joy, we have no time for it — and neither should our customers.”
Address: 2601 N. Milwaukee Ave., Chicago, Illinois, 60647
Best Place to Hit Before a Concert or a Game: District Brew Yards
This venue isn’t near Wrigley Field. Instead, you’ll find this hybrid of collective brewing facility, taproom, and communal gathering spot near the United Center, home of the NBA’s Chicago Bulls, the NHL’s Chicago Blackhawks, and music acts big enough to pack such arenas. The space contains a quartet of active on-site local breweries and a beer hall boasting 40 taps’ worth of its collective craft IPAs, ales, sours, and stouts, among other styles. Schneider specifically recommends checking out the creations of Burnt City Brewing, a pioneer of the Chicago craft beer scene that moved its brewery into the Yards in 2019 after more than two decades in the city’s Lincoln Park neighborhood. Light ales and bold, juicy IPAs are Burnt City’s stock and trade, and it’s not afraid to play around with different techniques like aging its creations in wine barrels.
Tip Jar: While there are plenty of drinking establishments around Wrigleyville, drinkers over a certain age may wish to refrain from going there for a pint. Bartenders and hospitality types tend to pooh-pooh the area due to what might best be described as “frat boy energy.”
Address: 417 N. Ashland Ave., Chicago, Illinois, 60622
Best Place to Play It Safe: Miller’s Pub
Established in 1935, this establishment wasn’t quite around to see Prohibition’s end, but it comes awfully close. This hardly matters, though, as the bar’s vintage ethos shines through, making it the ideal option for bringing friends or parents who are less excited by the modern cocktail scene. “Miller’s is about as old school as you can get in Chicago,” says Schneider. “It’s one of those places where the bartenders and servers have been there for 40 years.” Classics like Martinis and Manhattans appropriately dot the drinks list, which further adds to the ambiance. At the same time, Miller’s does offer its fair share of pre-Prohibition and Prohibition-era cocktails, including a few riffs: The Bee Danish, for instance, is a take on a Bee’s Knees featuring aquavit in place of gin.
Address: 134 S. Wabash Ave., Chicago, Illinois, 60603
Best Place to End a Big Night Out: Scofflaw
This Tales-nominated, gin-focused Logan Square bar is the antidote for bar crawls that end with a bowl of stale pretzels or an even more stale beer. The venue’s tidy slate of post-11:00 p.m. options is compact, but bites like the whipped feta and roasted warm cauliflower dip or the pho beef pierogi feature just enough fancy flair to keep things interesting without drifting into overly complicated territory. The accompanying cocktail menu also posts a handy glossary of each ingredient used in every one of its homemade creations, a neat touch that’s educational without being obnoxious. This eliminates the guesswork about what’s in a drink, giving you extra time to debate the merits of ordering a classic Irish coffee or a drink like the Polaris, featuring barrel-aged genever, quinquina, amaro, and sweet vermouth. There’s no losing answer here. After all, you’re in Chicago, sitting Big Shoulder to Big Shoulder with the stormy, husky, and brawling. You’ve already won.
Address: 3201 W. Armitage Ave., Chicago, Illinois, 60647