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Coming Soon Bar Pilsen

In the tradition of the taverns and music halls that have connected neighborhoods and neighbors across the city for generations, Kacy and Bobby Middleton, the husband-wife owners of metal fabrication company Wayward Machine Co., and Kevin Heisner, the designer, artist and owner of Heisler Hospitality and Hue Inc., are soon opening the doors to The Giant Penny Whistle at 1854 S. Blue Island Ave. in the heart of Pilsen.

Housed across adjoining storefronts in a late 19th-century building, bearing the marks of modern craftsmanship and mementos from other long-gone Chicago bars, The Giant Penny Whistle is a welcome place for meeting up any night of the week: over well thought-out cocktails or just a shot and a beer; to listen to live music or dance late while a DJ spins.

Unassuming from the street, The Giant Penny Whistle is surprising in scale, detail and yet simplicity once you step inside. Two deep storefronts make up the whole, connected by arched pass-throughs original to the building.

The tavern on one side, which will open late summer/early fall, is a neighborhood gathering spot that serves just a drink menu. The music hall, opening later this summer, will host local and touring bands, musicians and DJs of all genres who have outgrown the city’s smallest clubs. As the only midsize live music venue on Chicago’s Near South Side, it will be a forum for performers eager to leave their mark on the city’s rich music-filled scene.


The Giant Penny Whistle blends history and craftsmanship, old and new, in a 5,000-square-foot space that had been home since the 1970s to Tito’s Hacienda, a taqueria and bar.

The tavern’s centerpiece is a 37-foot-long standing-height bar dating to the 1940s, now restored and outfitted with vintage brass beer taps and custom bar stools. A second vintage bar on the music venue side, also standing height, was salvaged from McCuddy’s Tavern. The Bridgeport saloon, reportedly one of Babe Ruth’s favorite watering holes, closed in 1989 after nearly 80 years.

Peeling paint throughout the tavern was left as is. A newly installed parquet floor pays homage to dance halls of an earlier era. Comfortable booths line the walls and communal high-top tables run down the center, with space for 100 guests in all. A pinball machine and a pool table area with space for a DJ setup offer more reason to stay a while.

The original pressed tin and black marble wall tiles inspired the checkerboard design that repeats throughout the space, most apparent in the glass-paneled bathrooms lined with thousands of old 35mm photo slides, scenes of the past in Bridgeport and beyond—block parties, birthdays, weddings.

The walls could very well talk at The Giant Penny Whistle. A photo booth in a corner encourages guests to continue the conversation by leaving their photos to be incorporated onto those walls.


Meeting for a drink—not an overly wrought cocktail with ingredients you can’t pronounce, but a drink you can count on—is the thread that draws guests in to The Giant Penny Whistle, any night of the week.

General Manager Brad Hoffman developed the menu of beers and cocktails, inspired by the history of Pilsen, the tavern’s weathered walls and the memories and moments embedded within, documented in those vintage photo slides.

Two of the eight draft handles will always pour Pilsner Urquell and Pacifico Clara. Pilsner Urquell originated in Plzen, Czech Republic; Hoffman chose it as a nod to Pilsen’s roots as a Czech settlement in the late 1800s. Pacifico Clara, a similar style of beer from Mazatlan, Mexico, represents the neighborhood’s shifting cultural identity to a predominantly Mexican one.

The cocktails—there are four—riff on the wedding-day adage: something old, something new, something bitter, something blue. One is a classic drink, one an original and one a low-proof cocktail in the Italian aperitif style, with the ingredients rotating by season. The fourth, The Blue Island, is the house cocktail. It will always be a fizzy pisco cocktail in some form, and it will always be blue.

The rest of the menu offers a rotating selection of canned and draft beers featuring macrobrews as well as craft beers from Chicago’s Off Color, Hopewell, Marz and Whiner breweries.

There is no food menu, but guests are welcome to bring food from the neighborhood’s many restaurants.


The Middletons live in Bridgeport. Their metal fabrication company in Pilsen, Wayward Machine Co., is known for its hand-crafted designs featured in other Chicago restaurants and bars. Heisner is an artist, designer and owner of Hue Inc. and Heisler Hospitality, which oversees such restaurants as Bad Hunter and Estereo, among the places where Wayward’s work can be seen. A Little Village resident, Heisner also co-owns Pleasant House Pub in Pilsen.

Hoffman, who lives in Pilsen, was the shift manager and a constant presence behind the bar at Estereo since shortly after its opening three years ago. Talent Buyer Dan Coleman is a longtime music promoter from Indianapolis now living in Pilsen and the founder of Spirit of ’68 Promotions. Sound Curator Daniel Villarreal-Carrillo is a Pilsen-based drummer, DJ and member of the band Dos Santos.

The Giant Penny Whistle’s name is a reference to scientific experiments from the 1960s that explored the effects of low-frequency sound on the human body.

The tavern will be open daily from 3 p.m. to 2 a.m., and until 3 a.m. on Saturdays.


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