The 16 Best Old Man Bars In Chicago

By Lisa White in Best Of on May 13, 2015 8:40PM

There is something charming and inviting about the dimly lit, wood paneled confines of those dives known as "old man bars." You know the spots, those corner joints with their door sometimes propped open, offering a glimpse of the day drinkers and retirees sipping pints inside. Or the cozy confines of a cash-only cramped bar, the regular at the end eyeing you suspiciously as the jukebox (or small radio) cranks out classics from the '70s. They are little slices of nostalgia peppered in around Chicago.

Today we share some of our favorite old man bars in the city. From classic day drinking haunts to well known spots that might not seem it on the surface but are truly an old man bar at heart, here are some of our favorite places for cheap drinks and good people watching. And make sure to bring some cash, most of these places aren't the credit card type of establishment.

Richard’s
The smell of cigarettes is baked into the walls of Richard’s, a sure sign that it’s a prime location for gathering folks from an “older generation.” The vibe is super laid back and low-key, a welcome respite from the raucous rumble coming from Emmit’s Irish Pub and all the 20-somethings within looking to get laid. The room is dark and cozy, even when the bar opens its doors at 7 a.m. In fact, one of my personal requirements for a bar to qualify as an old man bar is that it’s the sort of joint that still feels like it’s 3 a.m. even when the noontime sun shines brightly outside. Step out of this dimension and enter a room suspended in time and go check out Richard’s. — Jim Kopeny / Tankboy

Richard’s Bar is located at 491 N. Milwaukee Ave.


Sky Ride Tap
If you love cheap whiskey, classic rock, country music and geriatrics, the Sky Ride Tap is one of the better places downtown to spend your afternoon. Nestled in under the brown line tracks, it’s one of the lovely dark spots in the Loop to escape tourists, office workers and judgement. Depending on when you arrive, it’s a mix of retirees, co-workers unwinding after a day of work and day traders grabbing a round. The bartenders are blond, tan and friendly and treat their regulars like family. They’ve got all types of dusty, nefarious looking liquors on their shelves but stick with the cheap standbys. The walls are wood panel, the lighting is bad and the music is wonderful. Belly up to the bar, grab a frosty one and strike up a conversation with the friendly regulars about how the weather is. It’s a delightful way to spend an afternoon downtown. — Lisa White

Sky Ride Tap is located at 105 W. Van Buren St.


Frank & Mary’s Tavern
The first time I walked into Frank & Mary’s, the grandmotherly woman behind the bar gave my friend and me a long, head-to-toe assessment before helpfully offering, “So you’re here for the Zombie Dust?” She’s clearly used to sussing out the hipsters and craft beer heads who venture up Elston for the hard-to-find Three Floyds APA on draft, but it can’t be difficult when the rest of the clientele is composed of single, middle-aged men nursing High Lifes while half-watching the Cubs on the tiny corner-mounted TVs. Pull up a stool at the Formica wood-grain bar and nurse that Zombie Dust like you’ve got nowhere else to be. — Lizz Kannenberg

Frank & Mary’s is located at 2905 N. Elston Ave.


The Cafe
A nondescript storefront that claims it's a "restaurant" (I've never seen anyone eating here) hides this low-key bar full of neighborhood folks where you can lounge on couches under IKEA lamplight with a crap beer or shoot some pool. There happens to be a beautiful tin ceiling too, indicating that people have probably been drinking under this roof for a long time.— Melissa McEwen

The Cafe is located at 5115 N. Lincoln Ave.

The Chipp Inn
Neighborhood bar or your uncle’s man cave? It’s a thin line that The Chipp Inn dances but I love it for what it is. A few things you might spot on any given afternoon or evening at this tiny West Town tavern: delightfully tacky and mildly offensive wall decor, a seemingly communal vegetable and cold cut tray and conversations held in a fluid mix of various European languages. It’s not all intimidating for the first timer though. There’s also a pool table, juke box and cheap drinks to enjoy. — Katie Karpowicz

The Chipp Inn is located at 832 N. Greenview Ave.


The Levee
Living in Logan Square there’s no shortage of new places to grab a fine cocktail or craft brew. But there are some nights where instead of sampling new spring libation menus or tulip glasses of beer, my South-Suburban instincts take over and I crave a High Life and a game of pool. That’s when I venture a little west on Fullerton Avenue to The Levee. Dating back to 1928, the spot has evolved over the years from a popular nightclub to a burger joint. But since 1979 the spot has been packed with Chicago sports memorabilia, plenty of bar games (even a free throw hoop!) and a pack of regulars that you could mistake for SNL Superfans. The accents are thick (the bar is also known as Da Levee), the beer flows, the Sox versus Cubs arguments are constant and the bar owners are some of the nicest you’ll find in the city. Be sure to bring cash, pick out some crowd-pleasers on the jukebox and cozy up for a few at the bar. — Gina Provenzano

The Levee is located at 4035 W. Fullerton Ave.


Old Town Ale House
O.K., before you jump down my throat and holler about the fact this place is overrun by yuppies and college students at night, I’d like to make the point that if we’re using old men day drinking in an establishment as the demarcation line, Old Town Ale House fits that bill. While yes, the younger crowd flows in after the sun sets, in daylight hours the stools are filled with a totally different crowd sipping their cold brews and arguing over the low hum of the jukebox kicking out classics from another era. So get there when they open in the afternoon, grab a mug and take it all in — Jim Kopeny / Tankboy

Old Town Ale House is located at 219 W. North Ave.


The Teddy Bear Lounge
Northwest Avondale may be a hot real estate commodity due to its proximately to Logan Square, but this sleepy ‘hood still boasts more than its fair share of working class-dependent old man bars. Perhaps the old man-iest of them all is tucked into the ground floor space of a relatively modern-looking three unit condo building on Pulaski, a facade that belies the cheap beer, plentiful well liquor and boisterous conversations in Polish that make the Teddy Bear a true bastion of the neighborhood’s past. Add to that $1 Old Style drafts, a pool table that is usually available, barmaids in traditional Polish frocks and a nightly cheese and cracker spread and it’s no wonder this is a favorite gathering place for men of a certain generation. But don’t worry - they welcome new blood with open arms (and maybe a turn or two on the dance floor). — Lizz Kannenberg

The Teddy Bear Lounge is located at 3513 N. Pulaski Rd.


Bob Inn
Tucked away just far enough from the revelers that pack Milwaukee Avenue bars in Logan Square is Bob Inn, a tiny watering hole for Sox fans of a certain age, longtime neighborhood dwellers, and the odd off-duty cop or two. The inside is decked out in wood paneling and framed art reminiscent of your uncle’s basement, and entertainment includes a pool table, a jukebox, and free Golden Tee. If those diversions don’t suit you, a TV sits above the bar, quietly playing the day’s news or a ball game. As early as 9:00 am every day you can come in for a cold Busch and an easy chat with the faithful clientele. When you spot the clover-studded sign outside, you’ll know you’ve made it. — Carrie Laski

Bob Inn is located at 2609 W. Fullerton Ave.


Exchequer
Exchequer is one of those Loop bars that has graced Wabash Avenue for ages. The storied history of its location, once a bar called the 226 Club frequented by Al Capone, it is a sort of time capsule that also happens to have great beer and cocktails, as well as some of the best pizza in the city. The atmosphere doesn't stop with history, though. This is a bar chock full of regulars staring up at the Blackhawks or Cubs game or having heated political discussions or sharing neighborhood gossip. Exchequer is akin to the idealistic model of Cheers where these regulars are men and women who have been sitting in those barstools for years and everyone knows their name. At night many students from nearby colleges start to filter in, but the regulars are the ones there before the evening starts or when evening just begins to usher in some twilight to this essential drinking spot along one of Chicago’s most iconic arteries. — Carrie McGath

Exchequer is located at 226 S. Wabash Ave.


Loop Liquors
A two-way accessible through one door only, this Loop Liquors is, shockingly, not in the Loop. The diverse array of storefronts on Chicago Ave between Ashland and Damen still hold strong to their roots. There aren’t many bar stools here, but if you can’t snag one, their selection of six packs to-go has improved even if the decor hasn’t.— Kristine Sherred

Loop Liquors is located at 1610 W. Chicago Ave.


Maria’s Packaged Goods and Community Bar
I know already some of you are going to rip me to shreds for including Maria’s, but hear me out. Yes, they’ve become a favorite hipster cocktail spot. Evenings at Maria’s include craft cocktails, bearded hipsters and DJs spinning soul music. But, during the daytime, it’s got so many of the classic trappings of an “old man” bar and is one of my favorite places to spend an afternoon. First off, it’s a fine example of a classic Chicago "slashie"— half liquor store, half neighborhood bar. The longstanding matriarch, Maria, is usually sitting nearby, keeping a watchful eye and chatting with customers. And it’s the perfect spot to grab a meat pie and a pint, since Pleasant House is next door and will happily deliver your grub to you at the bar at Maria’s. During the day I’ve seen a mix of guests, from construction workers on their lunch break to older men sipping beers to the bearded youngsters that tend to takeover the bar in the evening. Everyone coexists over pints from one of the more thoughtful selections of craft beers in the city. It’s beloved by many and if you’ve spent any time there, you’d know why. Maria’s is a true neighborhood spot for everyone to enjoy. — Lisa White

Maria’s is located at 960 W. 31st St.

The Green Mill
Wait (you’re saying) the Green Mill is a happening joint packed with jazz-loving hipsters and yuppies! It is indeed. After 6 o’clock. Stop by earlier, say around 4, and you’re likely to catch a glimpse of what Uptown might have looked like 30 years ago. Gnarled gentlemen of a certain age batting around opinions on the topics of the day (“Goddam Ricketts” or “That Emanuel is a fucker”) while nursing a short beer. Personally I recommend ordering a double Old Overholt on the rocks, the perfect complement to the weak rays of sunlight which struggle against the dignified gloom that is the Green Mill’s bar in the hours before sunset. — Rob Christopher

The Green Mill is located at 4802 N. Broadway.


Rossi’s Liquors
A poorly-lit dive on River North’s State Street, Rossi’s is popular among newspaper writers and other people who hate themselves. Its uninviting facade only somewhat belies the cozy interior, which features a curved bar, jukebox and a large selection of affordable drinks. One of River North’s few remaining dive bars, Rossi’s is open from 7 a.m. to 2 a.m. and is said to attract office workers and construction workers alike. Rossi's also keeps it classy with on-site liquor store cases where patrons can buy drinks to take home.—Rachel Cromidas

Rossi’s is located at 412 N. State St.


Rite Liquors
Rite Liquors is the kind of place you go after all the bars are closed so you can sit there just waiting to be served the second the liquor law hour strikes morning. If that’s not an old man bar, I don’t know what is. — Jim Kopeny / Tankboy

Rite Liquors is located at 1649 W. Division St.

The Cove
Just a few blocks from the lovely views at Promontory Point, The Cove is an ideal spot to stop and grab a round when visiting Hyde Park. The bartenders are friendly, the booze is simple and drinks start pouring before noon. Enjoy a pint while President Obama smiles down on you from the giant mural on the wall or catch a game on one of their televisions. It's dog friendly, so you might get to mingle with a pooch or two while you rub elbows with both U of C students from nearby and locals from the neighborhood. —Lisa White

The Cove is located at 1750 E. 55th St.