The Whistler: 15 Years of Cocktails & Live Music 


For 15 remarkable years, The Whistler has been a beloved fixture in the heart of Logan Square. This iconic craft cocktail bar and live music venue is celebrating its anniversary during the last week of September, and we think it’s the perfect party.

Wednesday, September 27th: A Night of Jazz

In honor of 15 years of weekly jazz nights, The Whistler is reuniting with Matt Ulery’s Loom, the first band to grace its stage. Matt Ulery, once a promising up-and-comer, has since become a leading figure in Chicago’s vibrant jazz community. The performance kicks off at 9 pm, promising a groovy evening of live music.

Thursday, September 28th: Cocktail Recipe Release Party  

The Whistler Cocktail Recipes

The Whistler has always been known for its innovative cocktail program. To celebrate this legacy, owners Billy Helmkamp and Rob Brenner are releasing a pocket-sized recipe guide titled “The Whistler: Cocktails (2008 – 2023).” This booklet will feature 25 cocktails that have been the highlights of The Whistler’s first 15 years in business. Each cocktail is accompanied by step-by-step recipes and detailed information about its history and character. You can get your hands on this delightful booklet at The Whistler from 6 pm to 2 am.

Friday, September 29th: For One Night Only  

For the grand finale of The Whistler’s three-day anniversary celebration, something special is in store. Billy Kalb and Dustin Drase, the dynamic duo behind the TTTTotally Dudes and owners of Cole’s Bar, are coming out of retirement for a one-night performance. TTTTotally Dudes was the longest-running monthly party at The Whistler, captivating audiences from January 2009 until February 2020. From 9 pm to 2 am, The Whistler welcomes them back for a night of nostalgia. Plus, a special shout-out to their customary last song of the night: Seal’s “Kiss from a Rose” entails a full-bar sing-along that’s not to be missed.

So, join The Whistler this week as they celebrate 15 years of crafting exceptional cocktails, curating live music, and creating lasting memories in the heart of Logan Square. It’s a testament to the enduring spirit of this neighborhood gem!

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