Hey Chicago bar hoppers!
When we’re showing clients around Chicago, we talk a lot about what gives different neighborhoods their character. And something that always comes up is the local watering hole. Where’s the best place to grab a drink? The answer often sits on a corner somewhere, usually in a bar that’s been there longer than anyone can remember.
Although there are plenty of trendy new places to grab a cocktail, Chicago has these old bars that are worth checking out. They’ve outlasted economic crashes, watched neighborhoods change completely, and somehow haven’t lost their character through all of it.
Here are some of our favorites, and we hope you find one that feels like the place where everybody knows your name.
The Berghoff
The Berghoff opened way back in 1898. After Prohibition ended, they got Chicago’s second liquor license because they opened one day too late to be first. Since then, it’s been in the same family for four generations!
You can sit at the same mahogany bar where people have been drinking Berghoff beer since before Henry Ford introduced the Model T. The stained-glass windows are original, and the dining hall looks exactly like it did decades ago.
Downtown Chicago has undergone significant transformation over the last 100 years, but inside the bar, time seems to have stood still. Office workers eat lunch next to tourists, and the German food hasn’t changed much either.
Green Door Tavern
The Green Door Tavern sits in a wooden building from 1872 and was built right after the Great Chicago Fire. The bar opened in 1921 as the Huron-Orleans Restaurant but during Prohibition, the bar was accessed through a basement door.
“Green door” was code for places serving illegal alcohol. The floor still slants because the 150-year-old building has settled over time. Downstairs, The Drifter (a speakeasy) operates in the same basement where people drank illegally in the 1920s.
Billy Goat Tavern
William “Billy Goat” Sianis opened the Billy Goat Tavern in 1934, and it became the hangout for Chicago newspaper reporters. You would regularly see Tribune and Sun-Times writers drinking at the same bar despite working for competing papers.
Mike Royko, the 1972 Pulitzer Prize winner and longtime Chicago newspaper columnist, would be found here. The walls are covered with old press clippings and photos from those days. Sam Sianis also cursed the Cubs in 1945 when they kicked him and his goat out of Wrigley Field. We all know it took the Cubs 71 years to win another World Series.
Green Mill
Green Mill started in 1910 as part of an amusement park, and during Prohibition, Al Capone supposedly had a favorite booth with views of both exits. There was even a secret door behind the bar leading to tunnels for moving liquor.
Live jazz plays seven nights a week. The velvet booths and green neon sign you see are original. Musicians know they’re playing at one of the country’s oldest jazz clubs, and the history and significance aren’t lost in their performances. They also do poetry slams and variety shows, keeping things current.
Simon’s Tavern
If you’re in Andersonville, look for the brightly lit neon fish holding a martini. That’s Simon’s Tavern. Simon Lundberg ran a Swedish speakeasy in the basement during Prohibition, then moved upstairs in 1934 when alcohol became legal.
The bar has had maybe three owners total since then. In winter, they make glögg, and the jukebox is loaded with classics. Locals say there’s a ghost from the speakeasy days, but she minds her own business and won’t bother you (unless you get really rowdy).
The Hideout
The Hideout can be found on an industrial side street, located in an old, frame house. Although city records from 1919 are missing, the establishment was open during Prohibition before officially obtaining a license in 1934.
In the past, it drew a large number of factory workers. Nowadays, it hosts indie bands, weekly soup nights, and political events. Christmas lights hang year-round, beer is cheap, and sometimes the bartender performs later. All around, it’s a fun place to check out.
Old Town Ale House
Right across from Second City, you’ll find the Old Town Ale House. Bruce Elliott owns it and has covered the walls with his paintings of customers and politicians, often naked. Roger Ebert called it “the best bar in the world that I know about.”
It stays open until 4 AM every night, and is a hotspot for comedians and service workers. If you’re stopping by, expect cash only, rickety furniture, and dim lighting. And a fun fact, John Belushi used to drink here.
Rainbo Club
Nelson Algren wrote “The Man with the Golden Arm” while drinking regularly at the Rainbo Club. That was in the 1950s, but the bar hasn’t changed much since opening its doors in 1935.
Liz Phair shot her “Exile in Guyville” album cover in the photo booth during the ’90s when Wicker Park was still cheap enough for musicians. Pop by for a drink and you’ll see that it still has the vintage Schlitz sign and mismatched furniture. And they take cash only.
Gold Star Bar
While you’re at the Rainbo Club, you can go down the street to check out Gold Star Bar. It opened in 1938 and has the same historic dive bar feel. During Prohibition, Division Street was a bit of a rough neighborhood, known as Polish Broadway. Gold Sta started in those days with a ‘hotel’ above, rumored to have housed teenage Polish girls for illicit purposes.
If you’re into ghosts, it also claims to be Chicago’s most haunted bar. Lots of people have said to have heard footsteps, voices and phantom presences in the rooms above and in the bar itself.
Carol’s Pub
Opened in 1972 (and again in 2018), Carol’s Pub is a rare spot in Chicago where you can two-step to country music until 4 AM. After reopening following some renovations, it still maintained the country music and dive bar atmosphere. Live country bands frequently play classics; people line dance, and karaoke remains popular.
For a genuine feel of Chicago’s blue-collar musical past (complete with cold beer, a little sawdust, and Loretta Lynn on the jukebox), Carol’s Pub is a place you want to check out.
Shinnick’s Pub
Shinnick’s Pub has been on the same Bridgeport corner since the 1890s, and originally opened to serve workers and visitors from the 1893 World’s Fair. The Shinnick family took it over in 1938, and four generations have run it since.
Walk in and you’ll find pressed-tin ceiling, a hardwood bar, and White Sox photos on the walls. We recommend ordering a Guinness or whiskey and soaking in the history, because it hasn’t changed since the 1940s.
Buddy Guy’s Legends
Buddy Guy opened Buddy Guy’s Legends in 1989 after becoming one of the greatest blues guitarists of all time. We’re talking eight Grammys, Rock & Roll Hall of Fame, and all that. How legendary is this place? Eric Clapton and David Bowie have played here.
Every January, Guy still does a residency and plays every night to sold-out crowds who wait in line for hours in the cold. The walls display his guitars and awards, along with a collection of memorabilia, including gifts from B.B. King and Clapton.
If you’re a music lover, especially the blues, this is the place to check out. Oh, and they have good Cajun food too.
Kingston Mines
Kingston Mines has been Chicago’s longest-running blues club since 1968. Doc Pellegrino set it up with two stages so the music never stops. One band finishes, and the other starts.
Inside, you’ll find a no-frills vibe with picnic tables, neon beer signs, and no attitude. Legends like Koko Taylor and Magic Slim play here regularly. Run by the Pellegrino family, their motto is, “Hear Blues, Drink Booze, Talk Loud. You’re Among Friends.”
It frequently attracts college kids, tourists, and longtime fans for late-night barbecue and gritty, soulful music until closing.
Why They Matter
Over the years, many drinking spots have opened and closed, but these bars survived because they simply focused on serving their neighborhoods instead of chasing trends. Each one adapted without losing what made them worth visiting in the first place.
When we’re helping people figure out where to live in Chicago, places like these tell you something about a neighborhood that property values can’t. They show you communities with roots, where people actually gather and strengthen the culture and spirit of the local area.
Next time you’re exploring Chicago, skip the newest cocktail place and try one of these instead. You’ll learn something about the city that doesn’t show up in guidebooks.
And if you’re interested in exploring neighbourhoods that you haven’t considered yet, give us a shout and we’ll share some of our best neighborhood insights and stories.
