Ask any bourbon geek for the best bar in Chicago to drink whiskey at, and you’ll get one answer: Delilah’s. Run by owner Mike Miller, Delilah’s turned 30 last year and packs folks in for its collection of more than 1,000 whiskeys, including plenty of stuff you can’t find elsewhere, like house blended Scotch made in collaboration with Compass Box. The bar is very chill, with regular DJs playing all genres, plus pinball and pool tables. But perhaps what’s best about Delilah’s, a black-painted house in a fancier part of the city, is that the place has always known exactly what it is: A bar for folks who just want a good drink without all the fuss.

Nice to know: Look up at the chalkboard menu—there’s a daily whiskey pour, like Four Roses or Maker’s Mark, available for just two or three bucks.

Chicago’s River North neighborhood is mostly known for its slick sports bars and scene-y Italian restaurants. Amid all that, Rossi’s endures. Open since 1974, its very improbability—a dark, cash-only dive where the going drinks are draft Miller Lites, shots of Malört or cans of beer plucked from the coolers on the wall—is precisely what keeps it alive. That, and the longtime bartenders who are equal parts friendly and feisty, and who sling drinks for everyone from office workers to third-shifters who find themselves in need of a morning drink (Rossi’s opens at 9 a.m.). They are all drawn in by the inarguable charm of the spot that calls itself “Chicago’s Second Best Dive Bar.”

Nice to know: Rossi’s is also a liquor store, so grab a six-pack of something local on your way out the door.

Walking along Clark Street in Andersonville on the city’s North Side, you can’t miss Simon’s: The neon sign is, of all things, a fish wearing a Viking helmet and holding a Martini glass. That “pickled herring” reflects the neighborhood’s Swedish heritage and tells you a little about what you’ll find inside this 90-year-old cash-only gathering spot. Owner Scott Martin began serving brandy-spiked glögg with ginger cookies in 1994. It’s become the bar’s signature drink—another neon sign lets you know when “It’s Glogg Time!”—and draws folks from all over the city each winter. The rest of the year, neighborhood locals line the long wooden bar and fill in the back patio to down cheap beers and Malört, keeping a little of the old Andersonville alive.

Nice to know: If you miss the hot glögg season, you can try the bar’s frozen version in summer.

When Jason Burrell and Clark Fowler opened The Long Room in 2000, it instantly became one of the leaders in Chicago’s craft beer scene. The shotgun bar, outfitted with worn-in seating, a photo booth and back garden, is still a go-to spot for beer nerds seeking new releases and hard-to-find brews. But over time, the Long Room has evolved into something more: an all-day gathering place. In 2015, Burrell added The Sidecar at LR, which hosts regular and one-off food pop-ups. The bar also began to open earlier for coffee and breakfast, which brings in folks on their laptops. People come in for that, but also because they know they can easily shift into the evening with a cold beer.

Nice to know: Despite The Long Room’s focus on beer, it’s worth your time to peruse the house cocktail list for drinks like the carbonated Bazucca Fizz (bourbon, Zucca and sweet vermouth) or the tobacco Old-Fashioned.

The Matchbox is a sliver of a bar that’s famous for two things: Its diminutive size (the main bar is 460 square feet) and its signature powdered sugar–rimmed Margaritas and Gimlets. Open since 1945, the bar is decked out with chandeliers, disco balls and Christmas lights, giving it a festive feel year-round. The Matchbox changed hands right before the pandemic, and some updates, like a patio that tripled the bar’s seating, have helped it keep up with the times. But where it counts—those Margaritas, the friendly vibe—the Matchbox is the same as it ever was. 

Nice to know: Since this tiny space fills up fast, go when it opens around 3 p.m. if you want to guarantee a seat in the main bar.

This Wicker Park bar has been a mainstay of the neighborhood since 1936, and it still retains its oddball charm. A stage behind the bar has hosted all kinds of shows over the decades, rotating art installations and tinseled Christmas trees that go up in December. But more than anything, owner Dee Taira’s Rainbo Club has captured the feeling of something just so expressly Chicago. It’s where Nelson Algren drank. Liz Phair, too. And it’s where you can post up at the shamrock-shaped bar or tuck into the red vinyl booths and sip your beer as you take it all in.

Nice to know: Rainbo Club produces an annual calendar featuring photos of bar regulars taken in the photo booth; it’s free with a donation to the local food pantry.

In early 2024, Skylark co-owner Bob McHale sold the bar to a group of six employees, who vowed to keep the friendly Pilsen bar exactly the same. Chicagoans breathed a sigh of relief—the 21-year-old bar had earned its reputation as one of the city’s top dives, featuring an extensive beer selection with rotating local drafts, $4 Schlitz tallboys and snacks in the top-tier of Chicago bar bites, like tater tots served with Cajun remoulade. The dark green–painted bar is almost a shape-shifter; it’s spacious, so it can accommodate groups with ease, but still manages to feel cozy on the nights when you’re seeking just that.

Nice to know: Look out for regular specials, like a Friday night fish fry.

One of Chicago’s weirdest dives, Old Town Ale House is also its artsiest. The old-school saloon, which has been open since 1958, attracts performers and students from nearby Second City, actually-famous actors (Bill Murray and Michael Shannon are known to frequent) and people who just want to gawk at the bizarre art while drinking cheap Miller High Lifes or local draft beers. Current owner Bruce Elliott is an artist, famous for his oil paintings that line the walls—they range from portraits of bar locals to racy paintings of national politicians—and give this place the feeling of a bohemian art gallery. 

Nice to know: Prepare for your visit by picking up a copy of Elliott’s book, Last Night at the Old Town Ale House—noted Old Town fan Anthony Bourdain wrote the foreword.

Chicago is a huge music town, so there’s no shortage of great blues and jazz clubs to check out. But Rosa’s, which is tucked away in Logan Square, is where the locals go for the low-key ambiance and a welcoming vibe. The 40-year-old club offers blues shows five nights a week, and performers range from Grammy nominees to Chicago up-and-comers. Drinks are affordable and skew classic, and although there’s no food menu, you can bring in your own snacks—stop by Best Intentions down the street to grab a few fantastic burgers stuffed in a brown paper sack.

Nice to know: Seating is first come, first served, and the intimate club fills up fast, so make sure you get your ticket in advance.

There are few downtown activities more perfectly Chicago than grabbing a Martini at a bar and taking in the scene. Miller’s, which has been open since 1935 (it changed family ownership once, back in 1950, and also changed locations back in 1989) is all stained glass, leather booths and dark woods, making it a comfortable spot that, like any good establishment, can meet any need. Hungry? Order the barbecue ribs. With a group? The large space can easily accommodate you. Thirsty? You can get a solid classic or explore the strong local beer list. Tourists love it, but so do Chicagoans.

Nice to know: Miller’s is at its best during the Christmas season—warm up with a nutmeg-topped Tom & Jerry in a thick brown mug at the festively decorated bar.