There’s always a reason to drink in Chicago: to keep warm in the winter, to celebrate the fleeting days of summer, to toast a Cubs’ victory, to ease the sting of a Bears’ loss. Similarly, Chicagoans don’t discriminate when it comes to booze. They fancy an upscale craft cocktail, appreciate beers of all stripes, order margaritas by the pitcher, and can make a night of sipping bubbly.
Chicago has long been viewed as a food town, but thanks to big-name bartenders and innovative brewers and distillers, the drinking scene has exploded of late. (Oh, and there’s no shortage of beloved old dives.) The city is an embarrassment of riches when it comes to bars, and no matter where you roam, you’ll find a bartender waiting to pour you a drink. Here are the four neighborhoods most deserving of your boozing budget, and the must-visit bars within them.
Long on your radar for its ever-expanding collection of white-hot restaurants, this area’s drinking scene has become destination-worthy in its own right. Kick things off on the far eastern fringes of Restaurant Row (a.k.a. West Randolph Street) at CH Distillery, where spirits—including the flagship vodka made from organic Illinois grains—are produced onsite and provide the base for many a delicious beverage. Time your visit right for a guided tour (which includes a cocktail!).
Meander west on Randolph into the thick of things, and take refuge in the chill, tavern-esque environs of Lone Wolf. Heads up, Three Floyds fans: Here’s where to find the city’s best selection of the brewery’s beers on draft.
Switching gears, head across the street and find RM Champagne Salon tucked away in a cobblestone alley. Sip the namesake sparkler al fresco beneath the twinkling white lights or head inside the romantic, candle-lit bistro for oysters and chef Jared Van Camp’s steak frites.From there, it’s a 10-minute walk to Waydown, a rooftop lounge atop the chic new Ace Hotel. A live DJ and killer skyline views await—as does a stiff “Bird’s Eye” with Heaven Hill bourbon, grapefruit juice, raspberry, sweet vermouth, and Angostura bitters.
You could spend weeks drinking your way through Wicker Park, which butts up against its equally hoppin’ neighbor to the north, Bucktown. Start on Division Street at Bangers & Lace, a beer-lover’s nirvana with dozens of both locally and globally sourced brews on draft. May as well eat a currywurst, too—you’ll need the sustenance. For a taste of what the neighborhood looked like pre-gentrification, walk a few storefronts west to Zakopane, a wood-paneled Polish dive, where the Żywiec is cold and the jukebox is stocked with charmingly out-of-date tunes.For another taste of the old guard, take the seven-minute jaunt to Rainbo Club, a gathering spot for artsy types since the 1930s. Inside the stark space, you’ll find pinball, the ever-popular photo booth, and cheap (for the neighborhood) booze.
Make your way toward what’s arguably the city’s most vibrant intersection—the North/Milwaukee/Damen five-way—and join the patio party at Big Star. Don’t think, just order a margarita (but beware: they’re stiff!), snack on chips and guac, and delight in the unrivaled people watching.
The same hospitality group operates The Violet Hour across the street, but the similarities end there. This multi-room, candlelit beauty—with an ever-changing facade and a single light bulb designating its entrance—is one of the city’s craft cocktail pioneers. Try something from the seasonal drink list.
For your grand finale, look to the Robey Hotel’s rooftop lounge The Up Room. Everyone knows a pour of rare whiskey tastes best when accompanied by 180° skyline views.
It may have lost its hipster edge, but Logan Square’s food and drink scene just won’t quit. Make the ultra-popular gin bar Scofflaw your first stop. These are serious cocktails, but fear not: A user-friendly menu, complete with drink illustrations and an ingredient glossary, keeps the intimidation factor low. Cross the street to The Moonlighter for a griddled burger and a beer on the chill, dog-friendly patio. Grab a $2 draft rosé shot before you depart.Next, take Armitage Avenue three blocks east until you hit Parson’s, the patio party to end all patio parties. (The red- and white-striped umbrellas and scent of fried food are unmistakable.) The Negroni slushy is a rite of summer.
It’s now time to head to Milwaukee Avenue, the neighborhood’s main artery. Grab a bottled cocktail at Slippery Slope then hit the dance floor. Make sure to get in a game of Skee Ball before slinking into one of the red vinyl booths. Work your way farther up Milwaukee to the Latin American-inspired Estereo. The menu changes seasonally, but you’ll always find the signature Breezy: a highball served with your call of spirit, Yerba Mate, Falernum, lime, and soda.It’s a five-minute walk to your final stop, Billy Sunday. The dark, charming haunt sits on the south side of Logan Square’s monument park and features a robust, downright intriguing cocktail menu courtesy of Charlie Trotter alum Alex Bachman. Into vintage amaro and fernet? You will be before you leave.
Huge changes have swept through Wrigleyville since Tom Ricketts bought the Cubs in 2009. For starters, the area surrounding Wrigley Field boasts excellent new drinking options as well as plenty of loveable standbys. Case in point: Nisei Lounge, where your crawl begins. The circa 1950 dive possesses the neighborhood’s oldest liquor license and, should you be looking to escape game day shenanigans (with a round of darts, perhaps), this is your spot.
Turn the corner to Clark Street and start north toward the stadium. You’re probably in sports mode at this point, so pit stop at Slugger’s for a few swings in the batting cages and a round of mini bowling. A beer and basket of wings are necessary.
Continue up Clark Street, stopping just before you reach the Friendly Confines. The 30,000-square-foot Cubby Bear is impossible to miss—and always a party. When there’s no game (which shows on the five giant projection screens and 75 plasma TVs), there’s often live music.
Head across Addison Street to Mordecai, a bi-level bar from Matthias Merges and Alex Bachman (who’s also one of the visionaries at Billy Sunday) inside the tony new Hotel Zachary. You’ll find Wrigley’s most refined drinking experience here, plus a staggering 200 varieties of rare American whiskey. Just across the way on the plaza outside the stadium, Merges shows some love for beer, too: His polished pub Lucky Dorr pours custom brews from local names including Maplewood and Revolution—perfect for toasting the end of an epic night. Note: The giant soft pretzels do wonders for soaking up alcohol.