This 67-year-old family-run bar attracts Ukrainian Village and Humboldt Park cool kids and old-timers for free pool and affordable beers from Half Acre to Hamm’s. Read more.
Open at 10am most days and closing around when Letterman comes on the TVs, the bar looks imposing from the outside but sparkles inside like a vinyl-padded, wood-paneled midcentury rec room. Read more.
Next time you’re in the mood for a beer, forego West Town’s cookie-cutter lounges and hit up this place instead. Owner Gonzalez happily shares warm conversation and her delicious homemade Spanish rice Read more.
The barstools, church pews and La-Z-Boys are populated with students and Rogers Park locals chatting or playing chess. The bar is stocked with plenty of beers less than $5, including Berghoff Dark. Read more.
The bar now has a Bonnie and Clyde–meets-baroque look, and the clientele has gone from old men to young South Loopers. The new owners kicked lagers off the beer list to make room for 100+ microbrews. Read more.
Come nightfall, this coffee shop transforms into a cocktail bar, and the wine, beer and cocktail lists are tightly edited (think classics such as the Corpse Reviver). Read more.
At this sake lounge, you can rent a private karaoke room for two hours for $50 per person, which includes one to four bottles of booze, depending on the size of your group. Read more.
Flo, a youthful 86-year-old with a carrot top, serves up Old Style and MGD ($2.50), plus pierogi, stuffed peppers and cabbage rolls. Read more.
The jukebox is well stocked with R&B dusties, and when “Honky Tonk” by James Brown comes on, women at one end of the bar start clapping along. Read more.
Stake claim to the ringed couches, or take a seat at the bar to chat up friendly bartenders who can help you pick your poison (try the Key Lime Pie and Swedish Fish martinis). Read more.
Karaokers can nosh on Korean apps or make a special request for the off-menu Yummyberry cocktail ($6.50), a mixture of soju, pomegranate and housemade ginger simple syrup. Read more.
There’s a recession going on? Not in here. At the Elysian Hotel’s clubby bar, it might as well be Reagan’s ’80s—every texture is plush, every server is formal, and every drink is, um, about $15. Read more.
This bare-bones dive takes the prize for Chicago’s most irresponsibly named bar. That said, this is a friendly place to sip $1 PBR pints or down $5 Vegas bombs with factory workers and police officers Read more.
Those who reminisce about a time before craft cocktails will find comfort in 21-year-old Sidekicks, where nachos and chicken wings hold court with beer and whiskey. Read more.
The first thing you need to know about this second-story bar is how to find it: tucked between Blackbird and Meiji, up a flight of neglected stairs, into the den of Johnnie Walker Blue Label bottles. Read more.
At Artis’, soul never ended. The bar ramps up on weekends when blues bands take the stage, but is lively during the week thanks to a soul and R&B jukebox, nattily dressed regulars and bartenders Read more.
Get the regulars debating the bar’s origin (“In the ’20s, it was a Polish deli and a speakeasy,” says one; “When you leave, sometimes there’s ham,” says another) and you’re in like Honey Baked. Read more.
Tucked away in a corner off the basement-level food court, it’s a clean, contemporary sports bar that bustles during lunch, after work and during game time. Read more.
Arts organizations are used to benefiting from wealthy patrons, but a student bar? Richard Driehaus donated Gilhooley’s to Saint Xavier University in 2005 (students can use meal cards for pub grub). Read more.
The owner, K, masterfully dices and fries chicken, beef and pork, and intestines both large and small. Order the soju, but drink wisely: The rice-barley liquor is easy to drink…and 19 percent alcohol. Read more.
This club features one of the most active dance floors on the South Side. Expect to see blues musicians, slam poets or R&B songstresses light up the house on Thursday open-mic nights. Read more.
This black-windowed storefront houses a surprisingly sleek Bulgarian nightspot. Blood-red walls, plush black sofas and silver banquettes create a vibe worthy of the bar’s name. Read more.
The only alcohol-serving establishment in the Pullman area (the neighborhood’s original design forbade booze), the lounge stays open until 11pm on most nights (2am if it’s really rockin’). Read more.
A cozy Wisconsin supper club transported to Chicago’s Southwest Side, Richie’s has dished up hearty fare with an Italian accent for city workers in Mount Greenwood since 1999. Read more.
How can a bar sitting on prime Mag Mile property be unsung? It’s a mystery, but we don’t mind, because for an after-work cocktail there’s perhaps no better perch than one of this bar’s window seats. Read more.
Decorated with cushy armchairs and tchotchke-lined walls, it’s the cozier way to sip $2 beers, have a pierogi and catch up on Polish news. Read more.
Since 1984, this bar off the Mag Mile has been a low-key, well-hidden hangout for middle-aged gays. Regulars drink cocktails and chat over dance music thumping at a comfortable level in the cozy space Read more.
On Fridays, the bar hosts a regular who’s frequented Rose’s Lounge since it opened, a smattering of hipsters and pool-playing men who are clearly quite protective of their tavern and its matriarch. Read more.
As “Mississippi Queen” blares on the jukebox at this tavern opened in 1985 by Polish immigrants, municipal employees gather around the pool table and belly up to the bar for bottles of Zywiec beer. Read more.
One of the bar's owners, Steve, hosts a wacky version of bingo, dubbed “Stingo,” Wednesdays at 9:30pm. Read more.
The tavern, last rehabbed in 1949, features sparkly gold vinyl booths and a gorgeous Art Deco bar. Bud Light and AmberBock are on tap ($1.55 a pint), and vintage ads for the train line adorn the walls Read more.
When a bar has 4am hours, it’s usually a sign of personal sorrow if you’re there before midnight. Not so at Alice’s, where karaoke veers from expected to epic beginning at 11pm. Read more.
Drunks who stumble over from whatever Irish McSurly’s kicked them out will rejoice at the $2 drafts; locals enjoy a neighborhood lounge blocks from the ballpark but miles away in terms of attitude. Read more.
A beer-bottle-shaped shrub is a sign you’ve found dive-bar gold. The front room features a serpentine brass bar, while the back room walls are decorated with antique tools and Abe Lincoln prints. Read more.
Incoming planes pass startlingly close to Mr. C’s, a welcoming dive close to Midway Airport. By day, the bar draws carpenters and tradesmen; at night, crew members and flight attendants show up. Read more.
Sassy karaoke MC Bill Nowlin fills the stark room with his smooth singing voice, and if he likes your pipes, you earn a ring from his bell. Read more.
Expect to get manhandled at the Manhandler Saloon. This Lincoln Park hole-in-the-wall is stocked with bottled beers, rugged barstools, gay porn on the TVs and plenty of middle-aged discreet men. Read more.
Monthly karaoke nights and live-band appearances on the tiny stage keep the place interesting, but the real entertainment is interacting (or ducking interactions) with the bar’s cast of characters. Read more.
A mix of the neighborhood’s Latinos and Anglos come out for cheap burgers, chicken sandwiches and chops, plus daily drink specials like $4 pints of Spaten Oktoberfest Read more.
The Irish American Heritage Center’s in-house pub draws a cast of neighborhood regulars, as well as actors and theatergoers from its two resident companies, Seanachaí and Shapeshifters. Read more.
This tiny Art Deco bar serves pizza and booze to Edgewater gays and straights. For the past 29 years, the gorgeous 81-year-old Peggy Gelsomino has manned the ovens, making the dough and sauce herself. Read more.
Everyone is family at the Lighthouse. Bartenders call the owner “Uncle” and patrons “Sugar,” Bears games are celebrated with potluck barbecue, and a memorial board displays the obits of past regulars. Read more.
Ex-cop Tony Anthony’s down-home soul-food restaurant and blues lounge features country dinners of rib tips, chicken wings and catfish, drawing workers from the nearby board of education. Read more.
Run by the DANK German cultural organization, the Skyline’s third-Friday Stammtisch open house brings in Deutsche grandmas who pull dancers from the crowd; jazz attracts a younger set on fifth Fridays Read more.
While the Lodge is beer-heavy, featuring a rotating selection of German and Belgian craft brews, meads and Trappist ales, its Dark and Stormy cocktail is one of the best in or outside the city. Read more.
Featuring 60 bottled beers and 18 on tap, the bar releases new seasonal brews, many of which it created itself, every Wednesday—though the housemade cream ale and stout are available all year long. Read more.
Get crunk, cultured and coiffed all at the same place. This wine bar/hair salon/art gallery boasts a wide array of organic and ecologically sustainable vinos, as well as a full-scale salon. Read more.
Concoctions like the Warhol ($12)—a mixture of Mount Gay rum, pureed blackberries and raspberries, lime and simple syrup served in a glass made of ice—make it too easy to run up a steep tab Read more.
