May all your horse bets result in owning a classic dive bar.
Not every day does a winning Triple Crown bet serve as the origin story for an iconic dive bar, but such is the case for Chicago’s Whirlaway Lounge. Legend has it that a longshot bet on racehorse Whirlaway that went on to win the Triple Crown in 1941 served as down payment for the original storefront for the Whirlaway Lounge, the perfect kind of alcohol and gambling convergence tale to set the stage for a great Chicago dive bar in the city’s Logan Square neighborhood.
Whirlaway Cocktail Lounge’s first incarnation called Milwaukee Avenue home, reportedly a remodeled tire store and brainchild of the ticket-winning owner who ultimately moved on from bar ownership sometime around 1952. New ownership in the form of Emily Wisniewski started out with a literal bang when she made the news in 1953 after chasing a wood-be robber down the street, gun blazing and shots fired. The sly side-eye gaze she gave the newspaper when it ran the story can still be seen within the bar and sometimes trotted out by regulars.
Ultimately, the Chicago dive bar’s original location was marked for demolition to make way for that dreaded thing called ‘progress,’ forcing a relocation to the bar’s current address on Fullerton Avenue. The awning was inscribed at that time with the Polish word ‘Karczma’ that means tavern, an addition only recently removed after some confusion around the word and a desire for some simplification in signage. Wisniewski operated Whirlaway Lounge until the age of 70 before selling to the Jaimes family in 1980, a stretch of family ownership that remains intact today.
And from the Jaimes family comes Maria, unquestioned soul of Whirlaway Lounge and frequent sight within its walls, supported by her late husband Sergio, Sr. before his passing and now son Sergio, Jr. Today, the red awning looks as prominent as it ever did, a stark contrast from the classic faded tones of the residential buildings that surround Whirlaway Lounge. The brick façade receives a kiss of neon from a pair of signs nestled in two impossibly tiny windows that dot the front wall.
Inside, the layout doesn’t get any more classic as far as Chicago dive bars go, a shotgun-style, single room layout with a long bar on one side and a few short tables along the opposite wall. The stamped ceiling overhead provides a nod to the history of the space. In addition to the two windows up front, a few opaque glass blocks sit just below the ceiling to again let in only the suggestion of natural light rather than its full force. The picture game is strong here, from framed photos to the city to an immense mural of locals, a flurry of snapshots depicting the many faces that have come and gone over the years, many photos including a smiling Maria nearby.
As a Chicago dive bar, the traditional “Chicago handshake” offering of Malort and Old Style is in effect, but so too are a number of craft beer varieties beyond the usual dive bar suspects. Above the bar, a handful of aged photos can be seen, including shots of a horse that one can only hope is namesake Whirlaway, the cause of the proceedings below. Loyola pennants around the space give a nod to the nearby institution and board games can be seen in use and stacked up within Whirlaway Lounge to provide additional diversion.
Dive bars do not come much purer than Whirlaway Lounge, a no-frills Logan Square mainstay with a stark red awning that, Polish vocabulary or not, has drawn people in for decades. But the story here is really the origin of the traveling institution that is Whirlaway, the perfect dive bar romantic tale of fortuitous winnings and colorful ownership, creating a dive bar special enough to last through two locations, a wrecking ball, a pandemic and more.