The most legendary dive bars in Chicago
This subterranean haunt has had its home under the Tribune Tower since 1934, when Billy Sianis founded it. It’s best known for being the inspiration behind the Olympia Café Saturday Night Live sketch starring John Belushi. Chicagoans know it best not for its “Cheezborger” (which is quite good, actually), but as an old journalists’ bar, where reporters from the nearby Chicago Tribune would come for beers and grub. The place still retains its character, with customers bellying up to the bar to grab a drink or lounging next to the “Wall of Fame”—filled with yellowed newspaper clippings from bar regulars. And let’s not forget, there’s also the whole thing with the Billy Goat. —Elizabeth Atkinson
This low-key Hyde Park dive might remind you of your grandparents' basement—if your grandparents had a massive mural of Barack Obama in their home. Cheap beer and strong, no-frills drinks dominate the bar, where you can saddle up on stools and people watch the night away. Blue-collar regulars mix and mingle with students from nearby University of Chicago, creating one of the best crowds in the city. It's the kind of place you feel warm just walking into—even when the temps dip below zero in Chicago. Plus, they accept credit cards—a huge bonus in our book. —Morgan Olsen
If you’ve come to Rossi’s expecting to be coddled, you’ve come to the wrong place. Longtime bartender Desiree is a no-bullshit kind of gal. The dive itself is a rarity in River North; it's a cash-only spot that's been around for decades, which is evident as soon as you walk in the door (no offense). It's the kind of locals-only establishment that doesn't register on tourists' radar, which is fine for the dedicated post-work crowd. Don't leave without checking out the row of refrigerators in the back, where you'll find packaged beer to take home. —MO
Sure, at first glance L & L Tavern might look like your typical dive bar—but you’d be wrong. Known as the former watering hole of serial killer Jeffrey Dahmer (and rumors of John Wayne Gacy showing up in a clown suit), L & L Tavern has a bit more to it than your typical dive. Attracting both Lakeview residents and longtime regulars, you’d do best to sit at the bar, order a cheap PBR and maybe scroll through Dahmer’s Wikipedia page (doesn’t everyone read serial killers’ Wikipedia pages?). Who knows, you might even see a band member or two wander in after playing the Vic. —EA
This iconic music venue is a destination. Really. Tucked off the hustle and bustle of North Avenue, the Hideout sits amongst inconspicuous warehouses near the Chicago River. Built in a 100-year-old balloon-frame home, the bar hosts comedy shows, poetry readings, live music and regular events throughout the year. As you might imagine, it's morphed into a community center of sorts (plus Miller Lite) throughout the years. Because of that, their tagline, "a regular guy bar for irregular folks," is perfectly accurate. —MO
Most nights, you’ll find that Kingston Mines draws a long line of students and blues fans alike. Since the late ’60s, this expansive blues club has had musicians playing on one of its two stages seven nights a week. You have a choice at Kingston Mines: You can gulp down Coronas and huddle up by the stage or sit down at one of the long tables with whatever fried food fits your fancy. Regardless of your choice, Kingston Mines is dependable—it’s open 365 days a year including holidays, so you can listen to blues whenever you like. —EA
Just down the street from Second City, you'll find that this bar is favored by a mix of actors, comedians, neighborhood locals and newspaper guys. Oh, and Michael Shannon. It's had a bit of a tumultuous history (multiple owners, a fire), but it's still a local favorite. You'll find owner Bruce Elliott's paintings on the walls—from celebrities to Second City alum (both famous and not). It all comes with a healthy dose of booze to ease you through the night.
Rose has been presiding over the bar at Rose's Lounge with frosty mugs of Old Style since the ’70s—a time period that the decor still echoes. You'll find mismatched furniture, Christmas lights and large framed photos along the back of the bar. It feels like a basement, but it's friendly and divey all at the same time. Stop in for a game of pool or migle with the regulars in an environment that can only be described as "classic."