Phyllis’ Musical Inn

Chicago, Illinois

Field Note

Nothing adds color to the backstory of a dive bar quite like the presence of polka music, a prominent theme in the history of Chicago’s Phyllis’ Musical Inn, a Wicker Park staple since 1954. One of the first music venues in what quickly became a polka hotbed, the Chicago dive bar has endured the ups and downs of its surrounding neighborhood to today represent a divey link to the past in a quickly evolving corner of Chicago.

The space now known as Phyllis’ Musical Inn opened as a grocery store in 1908, undergoing a series of business & name changes that included a stint as Harriet’s Inn. Amid the space’s many incarnations, a young accordion player named Phyllis took the stage in 1945, ultimately meeting husband Clem Jaskot Sr. within those same walls. In 1954, Phyllis & Clem purchased the bar, renamed it to Phyllis’ Musical Inn and the business has stayed in the family ever since.

Polka’s rampant popularity in the mid-1950s prompted Phyllis & Clem to lean into the trend, opening what was at that time one of the first music venues in the Wicker Park neighborhood. Shortly after, the area became known as a polka hot spot with countless live music venues dotting Division Street, giving patrons numerous opportunities to bounce in and out of polka sets. Dubbed for a time as Polka Broadway, the area benefitted from the boom, Phyllis’ Musical Inn included.

As musical tastes shifted, Phyllis’ Musical Inn went away from polka in 1976, ushering in an array of musical genres as the neighborhood around the space shifted to a much rougher environment. Though numerous businesses fled the area, Clem & Phyllis added a few bars to the windows and decided to stick it out, eventually re-christening the bar as an all-genre venue in 1984 with an opening set featuring Buddy Guy and Junior Wells. They Chicago dive bar’s musical credibility extends to the present day, notably serving as the venue for Veruca Salt’s first ever show and My Morning Jacket’s first Chicago gig.

As the fortunes of the Wicker Park and Ukrainian Village neighborhoods have lifted over the years, Phyllis’ Musical Inn has remained unchanged, the structure’s same opaque glass blocks looking out onto Division Street. Clem Sr. passed in 1997, leaving Phyllis to preside over the space until her death at teh age of 93. Son Clem Jr. now manages and owns Phyllis’ Musical Inn alongside wife Ilene, thankfully preserving the many details that make the space unique, down to the striking keyboard & shot glass wallpaper picked out by Phyllis in 1955 affixed to the walls still today.

Despite Division Street’s progressive evolution toward ever more expensive eating and drinking options, Phyllis’ Musical Inn offers reasonable cover charges, attractive drink pricing and an environment that sits in stark contrast to the slightly more affluent businesses nearby. A colorful mural stretches along one of the bar’s interior walls, ultimately terminating in the small, slightly elevated stage in back framed by a depiction of the city of Chicago ringed in piano keys.

The structure’s original tin roof presides over a single room, a curved L-shape bar snaking through the space with lightly illuminated neon pillars behind. The full-wall opaque glass blocks that look out onto the street provide a picturesque backdrop to the drinking done inside Phyllis’ Musical Inn, letting in just enough light to suggest the presence of the sun without greatly disturbing the proceedings. Though the wood here has been treated with care and resurfaced over the years, the age of the space shines through in the best possible way.

Maybe most surprisingly is the presence of a beer garden discovered through a small door in the rear of Phyllis’ Musical Inn. The striking setting feels more private than seems possible for such a densely populated corner of Chicago thanks to tall walls that block out all manner of exterior noise. A basketball hoop can be found here, evening drinkers often taking a small break from the live music inside to shoot a basket or two before reentry.