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Every Wednesday at 8pm, dozens of people descend into a dim basement beneath the Den Hotel in Lakeview for an evening of comedy and cocktails at the Blind Wolf Comedy show. Each week, a rotating lineup of new, established and on-the-rise comics takes the stage to perform short, late-night-style sets for about an hour and a half. The best part? It’s completely free.
I first heard about Blind Wolf, hosted by local comedian Devin Glass, from a poster plastered on a traffic signal pole in Lincoln Park. When I finally made it out to a show this week, I was shocked that the experience I had was, in fact, actually free.
You’ll need to reserve a complimentary ticket on the event discovery platform Pie. I was able to snag one a few hours before the show. When I arrived about 20 minutes before showtime, there wasn’t a bouncer scanning tickets at the door, just Glass standing outside greeting us with, “You here for the show?”
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He led us down a narrow stairwell in a gangway next to the Den Hotel and showed us inside with a quick rundown of what to expect. We secured seats on a couch near the front, ordered a round of drinks (there’s no formal minimum), and waited for the show to begin over a game of Connect 4 that was sitting on a nearby table.
To my surprise and delight, audience members were actually chatting as they took their seats. In a time when it’s typical to see most people burying their heads in their phones to avoid any kind of interaction with strangers, it was refreshing to be in a space where connection is, mostly due to the venue’s intimacy, encouraged.
Shortly after 8pm, and after nearly 50 people piled into the subterranean room, Glass introduced the first comedian. Ten local and touring comics performed short sets, each featuring a mix of old and new material. Highlights included sets by the bartender, Nicky B (Laugh Factory, Zanies, Lincoln Lodge), Joe Medoff (Laugh Factory, Zanies, Lincoln Lodge) and Jon Boyd, who was in town from Phoenix.
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The energy was high, the performers were, for the most part, funny, and the entire evening was an impressive show of Chicago’s superb and diverse comedy scene. The lineup is a surprise each week, but you can follow Blind Wolf, which celebrates its first anniversary next week, on Instagram to see clips from recent shows.
It’s often hard to step out of the house without shelling out a small fortune, so finding this free show feels like uncovering a true hidden gem. It’s safe to say this is one of the best free things to do in Chicago.