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Logan Square, Humboldt Park, Avondale

The Whistler Turns 10, Celebrates With Live Sets And ‘Greatest Hits’ Cocktail Menu

The week-long celebration is a chance for The Whistler fans to bask in the bar's sameness.

The Whistler at 2421 N. Milwaukee Ave.
The Whistler
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LOGAN SQUARE — The Whistler isn’t old by most people’s standards — the cozy craft cocktail bar/music venue has called Logan Square home for just 10 years.

But the bar at 2421 N. Milwaukee Ave. is similar to Chicago’s oldest, most storied establishments in that its owners have honed in on what works and made it a point to never stray.

Case in point: Owners Billy Helmkamp and Rob Brenner have toyed with the idea of expanding the bar’s footprint over the years, but ultimately decided against it each time.

“It’s tempting, but why mess with a good thing?” Helmkamp said.

At its core, The Whistler is all about inventive-yet-affordable craft cocktails, $2 cans of PBR and live entertainment in a small, dim room — no gimmicks or frills. That will never change, Helmkamp said.

This week the bar is celebrating its 10-year anniversary — a decade of staying the same — with a calendar full of special events and a cocktail menu full of “greatest hits.”

Matt Ulery, a member of the first band to ever play at The Whistler, and Quin Kirchner are slated to perform at 9:30 p.m. Monday. 

Long-standing Whistler events like the “Relax Attack” jazz show, CHIRP Radio night and DJ sets from TTTTOTALLY DUDES and The Pleasure Principle, as well as a performance from local thrash-metal band Oozing Wound (Brenner’s favorite), will round out the week. The full calendar of events is listed on the bar’s website.

Drink-wise, folks can expect a rotating cocktail menu featuring old favorites from over the years. (Rosemary Collins, anyone?)

“In 10 years, we’ve had an unbelievable amount of drinks grace our menu,” Helmkamp said. “I wouldn’t even want to try guessing [how many]. I’d probably be so off it’d be laughable.”

Serving up those drinks will be a host of familiar faces, including Danny Shapiro, who used to bartend at The Whistler before he went on to open Scofflaw.

Ultimately, the week-long celebration is a chance for The Whistler community to bask in the bar’s sameness.

“If you look at us, we’re doing the exact thing we were doing 10 years ago,” Helmkamp said, reflecting back on the decade. “I think we’re doing it much better than we were because if you’re not getting better, you’re getting worse. That’s part of how we approach things.”

While Helmkamp and his partners were focused on staying the same, more than a dozen new bars, most of them specializing in craft cocktails, joined the neighborhood. They all came after The Whistler.

The influx of new bars doesn’t intimidate Helmkamp, who is friends with many of the operators.

“It’s my hope and ambition to lead by example I suppose. Do what you believe in, do what’s right, love what you do,” Helmkamp said. “I hope in five, 10 years, I don’t want to say we’re the grandfather — I think that’s maybe presumptuous — but something to that effect.”

Meanwhile, Helmkamp, Brenner and a third partner, Eric Henry, are busy getting their new bar/music venue, Sleeping Village, off the ground, which they opened just six months ago in an old cabinet store in Avondale.

Helmkamp said there are no new bar projects in the works — he and his partners are content running The Whistler and Sleeping Village. The latter wasn’t a concept hatched overnight; Helmkamp said they’d been talking about opening Sleeping Village for years before they finally took the plunge.

“It probably goes without saying, but we’re not looking to open a new place every six months. We really have no further ambitions beyond Sleeping Village,” Helmkamp said.

“We’re trying to take what we did in terms of bar programming and live music and do that in another neighborhood, take the lessons we’ve learned and apply them there,” he said.