The Best Dive Bars in Chicago, According to Bartenders

Sure, we like to sip perfect Boulevardiers while sitting on leather banquettes and nibbling house-made charcuterie—who doesn’t? But we also have moments when we’d rather just knock back Tecates in a room full of peeling paint and old-timers who smell like they’ve been fermenting in a jar of Newports.

When we crave equal parts solace and cheap entertainment, it’s the dark, seedy dive bar that we flock to. Off-the-clock bartenders feel the same way—when they’re done shaking daiquiris and inventing cocktails for the guest who wants something “refreshing but not too sweet,” they down shots and cheap beers, not fancy cocktails.

We asked nine of Chicago’s top barkeeps which dives they go to when they need a proper, no-nonsense session. After-hours (or on their day off), you might find them at these watering holes, sipping whiskey straight and feeding crumpled bills into the jukebox.

Annemarie Sagoi

Bartender/manager at The Drifter Favorite dive bar: Richard’s Bar (491 N Milwaukee Ave; 312-733-2251, facebook/Richards-Bar)

Sagoi says: “The jukebox is full of great music from the ’50s and ’60s, and the ambiance is definitely of another era. It’s even legal to smoke in there due to a grandfather clause. The bartenders are full of character and have been there forever. To top it off, they sell eggs! Hard-boiled eggs, at $0.75 each.” (Photo: Chelsea Ross/Yelp)

Micah Melton

Beverage director at The Aviary Favorite dive bar: Clark Street Ale House (742 N Clark St; 877-637-7133, clarkstreetalehouse.com)

Melton says: “Pluses are: a super friendly staff, good whiskey list, nice selection of beers on tap, and a 4am license. Before you even get up to the bar, one of the bartenders is already pouring you a drink. You can find me here drinking chartreuse, bourbon, gin and tonics, or High Life, and playing as much Hall and Oates as I have cash in my pocket to feed the jukebox.” (Photo: Christian Seel/Foursquare)

Wade McElroy

Director of Beverage Operations at Heisler Hospitality Favorite dive bar: The Matchbox (770 N Milwaukee Ave; 312-666-9292, thesilverpalmrestaurant.com/TheMachBox)

McElroy says: “The Matchbox is a small, neighborhood joint that has infinite charm. The bartenders are great, the drinks are huge, the daiquiris are rimmed with powdered sugar and come with a sidecar, and the whiskey selection is massive. A great mixture of old timers, hipsters, and neighborhood folks haunt the bar, and it truly feels like a Chicago institution. Love that friggin’ bar.” (Photo: Nathan Michael, Yelp)

Eden Laurin

Managing partner at The Violet Hour Favorite dive bar: The Owl (2521 N Milwaukee Ave; 773-235-5300, owlbarchicago.com)

Laurin says: “The Owl is a 4am bar, which makes it a great spot to go late-night. If you get in early enough, the bar is quiet and the perfect spot for a shot of whiskey and a hang. Grab a bar stool then stay and watch the crowd roll in, turning the space into a perfect location for people watching, dancing like you don’t care, and (obviously) more shots of whiskey.” (Chloe List/Yelp)

Phil Olson

Bar manager at Longman & Eagle Favorite dive bar: Rossi’s Liquors (412 N State St; 312-644-5775, facebook.com/Rossis-Liquors)

Olson says: “When I first moved to Chicago, I lived and worked downtown, and the area around State Street was full of tourist traps and corporate chains. Rossi’s was a breath of fresh air from all of that—except that the air was usually filled with smoke, and not at all fresh. Rossi’s is a dive in the truest sense. Anyone from any background could find themselves there and have a blast.” (Photo: Clayton Hauck/Yelp)

Eric S. Clarke

Bar manager at Bangers & Lace Favorite dive bar: Rite Liquors (1649 W Division St; 773-486-6257, riteliquors-chicago.com)

Clarke says: “Rite Liquors is my usual haunt, and it’s right across the street from the bar I run. It’s been around since the early ’70s when this neighborhood was losing it’s neighborly Ukrainian and Polish vibe for the gang-banger mix of Latin kings, gangster disciples, and others. Somehow the owner, Mike, managed to keep this gem afloat. It’s a slasher and has some history. Lining the walls of this place are shelves stocked with hundreds of thousands of dollars of bottled booze—bottles that are as warped as the bar itself. Among those bottles there are a few Stoli that still have ‘product of U.S.S.R’ on their labels, and I’ve found bottles of Old Forester from the early ’80s. Rite Liquors is a great place to wake up and go to just after dawn during a snowstorm. You can have civil conversations or deeply heated ones, while inhaling the bad perfume of drunk women mixed with the nasty smell of old beer. It’s a place to sit down and get f*cked up.” (Photo: Vimeo/Eric Clarke)

Charlie Schott

Bar Manager at Parson’s Chicken & Fish Favorite dive bar: Whirlaway (3224 W Fullerton Ave; 773-276-6809, whirlaway.net)

Schott says: “Maria is the most pleasant and amazing bartender. She makes you feel like part of the family, and she won’t let you drink too much!” (Photo: Clayton Hauck, Foursquare)

Paul McGee

Beverage Director/partner at Lost Lake Favorite dive bar: Delilah’s (2771 N Lincoln Ave; 773-472-2771, delilahschicago.com)

McGee says: “They have an amazing whiskey selection—including lots of stuff you can’t get anymore—plus cheap beer, a friendly staff, and an awesomely knowledgeable owner.” (Photos: Clayton Hauck, Delilah’s Chicago)

Michael Roper

Owner and bartender at Hopleaf Favorite dive bar: Cary’s Lounge (2251 W Devon Ave; 773-743-5737, caryslounge.com)

Roper says: “Cary’s seems out of place in a neighborhood now almost entirely populated by Indian and Pakistani immigrants who’ve opened dozens of sari shops, groceries, and restaurants. Among them is Cary’s Lounge, with its bright blue neon sign. Inside you’ll find a well worn bar, some high-top tables, and a pool table in back. For a dive bar, the selection of beer and spirits is impressive, and owner Pete Valivanis—who inherited the bar from his career bartender father, who first bought it in 1972—is a great classic cocktail maker. Don’t get me wrong: Lots of the regulars have not even noted the array of beverages available, and stay loyal to cheap shots and the same beer brands Pete’s dad served in ’72.

I go to a lot of exclusive, expensive, trendy, and high-design bars with huge beer menus, cocktails made by bearded mixologists with goofy hats that take 20 minutes to make and cost $20 a piece, and precious “small plates.” Some of these places are so reverent and uptight, it seems out of place to laugh or have fun. Some are fun, but the experience is a bit well-planned and pre-ordained. Sometimes I just want to go to a ‘normal’ bar with normal people. Not a ‘beer bar,’ a ‘sports bar,’ an ‘Irish’ bar, or a ‘gastropub.’ Just a bar. A bar like Cary’s.” (Photo: Facebook, Cary’s Lounge)
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