There are benefits to being old: you can speak your mind, claim confusion during awkward moments, and commit small crimes with little fear of retribution. Plus, if you're old AND a bar, you've got a shot at making our list of the 10 oldest bars in Chicago.
Since our knowledge of history extends about as far back as the latest episode of Pawn Stars, we called in local bar historians Jonathan Porter of Chicago Prohibition Tours and Sean Parnell of the Chicago Bar Project to help us assemble this list of the oldest bars in the entire city.
West Loop Opened: 1921
While the building was constructed in 1872 as one of the first structures to be built Downtown after the Great Chicago Fire, in 1921 it was converted into an Italian restaurant with a speakeasy in the basement. There's actually still a massive bookshelf that can be moved to reveal a hole in the wall that was once used to sneak in bootlegged kegs. Fun fact: Apparently nothing can destroy this place -- not fire, not its leaning structure (careful), and not even a car crash that once took out the structure’s Northeast corner.
Lakeview Opened: 1918
Before this place was overtaken by frat dudes and aspiring Coyote Ugly girls dancing on the bar, it operated as an innocuous-looking soda shop with a secret room called "Prohibition Willy's Speakeasy" in the back (still there today, now full of the aforementioned dudes). Since 1933 it has held the oldest continuous tavern license on the North Side, hence the signage. Fun fact: According to Dennis McCarthy's The Great Chicago Bar & Saloon Guide, "When the present owners were remodeling in 1974, they stumbled on a secret room in the basement full of White Horse Scotch and Portuguese brandy, without government seals of course, and in pre-twist top bottles."
South Loop Opened: 1914
This South Loop neighborhood joint takes a rather low-key approach to its storied history, simply stating on its website that: “A bar of one sort or another has occupied the current location for over 100 years." More specifically, the building was originally constructed by the publishers of The Wizard of Oz and once sat in a district surrounded by bars and bordellos. Fun fact: According to Chicago Bar Project, "the staff at Kasey's once wore T-shirts with the bar's slogan, 'Positively No Dancing', written on them. Rather than a rip-off of the Twin Anchors motto, the slogan originated from a city ordinance, perhaps intended to keep Kasey's from becoming a nightclub."
Old Town Opened: 1910
When Prohibition came about, this Old Town institution was converted into a speakeasy called Tante Lee Soft Drinks, with the front windows boarded up to obscure the illicit activity taking place inside. Featured in films ranging from The Dark Knight to Return to Me, this infamous ribs joint was also one of Frank Sinatra’s favorite hangouts back in the day. Fun fact: According to Chicago Prohibition Tours, one of Sinatra’s bodyguards "would stand near the pay phone inside to make sure that no one alerted any others that he was there." Apparently, Ol' Blue Eyes liked to dine in peace.
Uptown Opened: 1907
One of the country’s top jazz clubs was once a favorite hangout of Al Capone that operated openly during Prohibition, with the cops on the payroll. And when Capone’s favorite singer left the club to take another gig, the singer’s throat was slashed and part of his tongue was cut off in the dressing room. The club was originally designed as a tribute to the Moulin Rouge ("Red Mill") in Paris, and reportedly sits atop an elaborate system of underground tunnels. Fun fact: Apparently, each night, when Capone entered the bar, the bandleader would stop whatever they were playing and perform Capone's favorite, "Rhapsody in Blue".
The Loop Opened: 1898
Proud owners of Chicago’s first liquor license, The Berghoff is one of the only bars on this list that did not operate as a speakeasy during Prohibition, instead reportedly surviving on food and root beer sales alone. What they don’t tell you is that the iconic Downtown brewpub also operated as a men’s-only establishment until 1969, well past the date anyone deemed socially acceptable. Fun fact: In the early days, you could get a free corned beef sandwich with the purchase of a stein of Berghoff beer, originally brewed by Herman Berghoff in Fort Wayne, Indiana, before he relocated to Chicago for the 1893 World’s Fair.
Noble Square Opened: 1897
Not much is known about one of Chicago’s oldest bars. What we do know is that it dates back to 1897 and is said to have operated as a speakeasy during Prohibition. We also know that if you’re into the kind of cheap canned beer that always finds its way into dad’s fishing cooler, this is the place for you. Fun fact: It seems history has treated it well -- Esquire named it one of "The Best Bars in America".
Bridgeport Opened: 1890
Solidifying Bridgeport’s reputation as the city’s epicenter of booze and politics, this no-frills local pub's (formerly smoke-filled) back room has reportedly hosted enough shady political deals that the bar is also known as "Little City Hall". It's also believed to have been constructed for the 1893 World’s Columbian Exhibition. Fun fact: During Prohibition, access to the bar was gained through a complicated set of hallways and buzzers that included entering through an upstairs apartment.
Old Town Opened: 1885
Bathtub gin was prepared on the second floor above this former grocery store during Prohibition, with patrons entering the speakeasy through the side stairwell. It was the type of place where you went to buy some ground beef, some milk, some cheese, and put your mason jar on the counter and asked them to fill it up with the good stuff. Fun fact: Despite recent renovations, the antique wooden bar dates back to the bar’s inception.
Bridgeport Opened: 1881
As Chicago’s oldest continually running tavern, this South Side institution got its name from a mechanism that allegedly pumped beer from a former brewery located next door into the tavern during the days of Prohibition. Located across the street from the 11th Ward Democratic Party headquarters and a 15-minute walk from U.S. Cellular Field (you can park here for free with purchase of a meal during Sox games), the bar is a legendary hangout of former Chicago mayors and White Sox owners. Fun fact: According to 90-year-old Jack Schaller, who has lived above the bar for 37 years and has no shortage of stories, the tavern formerly housed a horse bookmaking operation and once hosted the 21st birthday celebration of none other than Richard M. Daley himself (photos not available).
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Located in a West Loop building built right after the Great Chicago Fire, this historic Irish tavern first opened its doors in 1921. It's gone through a series of owners over the years, and its latest name, The Green Door Tavern, comes from its history as a speakeasy during the Prohibition (a green door indicated the presence of a speakeasy). Today, it's an essential neighborhood dive with a great draft beer selection, whiskey, and old-school Chi-town cheer.
This South Loop neighborhood joint takes a rather low-key approach to its storied history, simply stating on its website that: “A bar of one sort or another has occupied the current location for over 100 years." The sort of bar you can expect now is one with a huge range of taps pouring delicious craft brews.
Famed for being Al Capone's favorite bar during the heyday of Prohibition, Green Mill Cocktail Lounge is now known as one of the finest jazz clubs in the country. The Uptown bar hosts live performances every night of the week, and the acts range from contemporary jazz bands and quartets to swing orchestras and solo guitarists. The cover charge is usually between $4 and $15, depending on the band. Note: Green Mill is cash-only.
The owners of Chicago's first post-Prohibition liquor license in 1933, The Berghoff has been bringing German food and drink to the Windy City for more than a century. The Loop institution opened before the Prohibition -- in 1898 -- but it really began as a brewery a couple of years before that. Now, it's known for its house brews (best when sampled in a flight of five), reubens, and old-world schnitzel entrees. Not surprising given its German roots, The Berghoff is a major player in Chicago's annual Oktoberfest celebrations.
Not much is known about one of Chicago’s oldest bars. What we do know is that it dates back to 1897 and is said to have operated as a speakeasy during Prohibition. We also know that if you’re into cheap canned beer you haven’t seen since you raided your dad’s fishing cooler growing up, this is the place for you.
Solidifying Bridgeport’s reputation as the city’s epicenter of booze and politics, this no-frills local pub's (formerly smoke-filled) back room has reportedly hosted enough shady political deals that the bar is also known as "Little City Hall". It's also believed to have been constructed for the 1893 World’s Columbian Exhibition.
Marge's Still was opened in 1885, and bathtub gin was prepared on the second floor above this former grocery store during Prohibition, with patrons entering the speakeasy through the side stairwell. The antique wooden bar is still there today.
In continuous operation since 1881, Schaller's Pump is Chicago's oldest bar. A former speakeasy, the Bridgeport tavern changed ownership at the end of Prohibition when George Schaller bought it and changed the name to what it is now, a play on "Schiller's pump," a device used to pump beer between breweries. The beer bar is a regular hangout for an unusual mix of local politicians and White Sox fans due to it being across the street from the district's Democratic Party headquarters and a short walk from U.S. Cellular Field.