The Whistler may be the one of the most talked about bars in Logan Square. Local artists praise the bar’s supportive stance toward the creative community, music lovers enjoy its eclectic array of live performances, and most of all, Whistler is famed for its cocktail menu.
However, the Whistler’s owners never set out to run a cocktail bar, but rather had the idea to turn an investment property into an arts space in Logan Square, at a time when a new crop of artists started flocking to the neighborhood, seeking shelter from rising rents in Wicker Park around 2005.

“It took us about three years to get everything going,” says Whistler managing partner Billy Helmkamp. “We had a lot of support in the neighborhood because we had a lot of time to talk to people about what we were doing before we even opened.”
Helmkamp, a veteran member of a Chicago arts collective, and a Logan Square resident for some 15 years, envisioned a space that would showcase music and other arts nightly in Logan Square. Running a bar was more of a logical afterthought than a mission. “We kind of said, ‘If we’re going to put on concerts, then I guess we should sell beer!” he says.

In 2008, on the night the Whistler opened for business, plenty of suds were on hand for what Helmkamp thought would be a beer-thirsty crowd. However, the small list of cocktails that Helmkamp and staff had thrown together for opening night generated such positive feedback that it became a signature for Whistler. “I guess we’re a cocktail bar now,” said Helmkamp to his business partner after that night, and nearly eight years later, the Whistler maintains a reputation as one of the best cocktail bars in Logan Square. That’s an impressive feat in a neighborhood that now has dozens of options for craft cocktails.
“I like to offer drinks that I would want to drink myself,” says Helmkamp of the lineup of libations that changes daily, allowing for bartenders to get creative as well as cater somewhat to seasonal preferences. “I didn’t want to offer four menus for four seasons, because Chicago weather just doesn’t work like that. But if it’s unseasonably cold one night, I want to give my bartenders the option to create a hot drink, for instance.”

Helmkamp also trusts the staff operating the bar to provide him with feedback about the music acts that play on the stage at Whistler, and like the cocktail menu, the entertainment schedule reflects Helmkamp’s own taste.
“In the beginning, I was working behind the bar all the time, so I would just book the kind of music I wanted to listen to,” he says. Today, Helmkamp is still in charge of all music programming at Whistler, and he features a wide variety of performers from jazz trios to experimental noise artists to DJs spinning classic soul on vinyl. And, in conjunction with Whistler Records, Helmkamp’s private imprint, local artists are releasing full-length records recorded live in front of Whistler audiences.

So, perhaps it doesn’t do the Whistler justice to just call it a bar. Inside and out, the space feels more like an after-hours gallery anyway, with rotating art installations in the storefront window, as well art and photographs adorning the interior walls. Owing to the vision of its owners and a little bit of serendipity, Whistler, one of the most intimate music venues in Logan Square, has become one of the best-loved and most-enduring cocktail bars in neighborhood.
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