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5 great Chicago-based podcasts you should be listening to

Written by
Aaron Rote

With so much music, comedy and art going on at one time it should come as no surprise that Chicago has a flourishing podcast community to help keep all of this culture in check. From explorations of the city’s complex history to impassioned film criticism to in-depth interviews with local comedians, Chicago’s podcast landscape is vast—you'll have no problem finding something to keep you entertained as you try to avoid an awkward conversation with your Uber driver. Hell, you might even learn something in the process. Here are five of the best Chicago-based podcasts to have locked and loaded for your next commute.

Curious City

Curious City’s innovative approach to investigative journalism makes it a must-listen for anyone who calls Chicago home. Engaged citizens can log on and pose random questions about any and every city-related occurrence, from “What happened to the former residents of Cabrini-Green?” to “Why do Metra trains run on the left track in the direction of travel?” Listeners vote on the questions they’d like to hear answered. Then Curious City goes to work, combining archival WBEZ stories with new investigations. The resulting podcast can be educational, heartbreaking or just plain weird, but it’s guaranteed to be 100 percent Chicago.


Film criticism podcasts are a dime a dozen, but Filmspotting has managed to rise above the fray by having just the right balance of reverence and irreverence. Every week the crew reviews a new movie, presents a "Top 5" list and acts out a scene (terribly) from a classic film. Hosts Adam Kempenaar and Josh Larsen disagree a lot, which makes for some really engaging and insightful conversations. The show can get especially great when Chicago Tribune critic (and famous contrarian) Michael Phillips joins the discussion. It’s as close to the spirited debates of the old Siskel and Ebert show that you’re likely to ever see (or hear).

Improv Nerd with Jimmy Carrane

Chicago is an improv city, and Jimmy Carrane is our most knowledgeable and enthusiastic tour guide. Each Improv Nerd episode opens with Carrane and a guest improvising a scene in front of a live audience and then sitting down for an in-depth conversation about the creative process. The former host of Studio 312 on Chicago Public Radio, Carrane has also taught at Second City, iO Chicago and Annoyance. The podcast is required material for anyone interested in breaking into the improv scene. And if the thought of performing in front of a roomful of strangers makes you break into a cold sweat, Improv Nerd still offers plenty of vicarious fun.

Wrestling With Depression

Marty DeRosa’s Wrestling With Depression is basically a Chicago institution at this point. Along with a weekly guest from the worlds of comedy, wrestling and beyond, DeRosa explores the dark emotions that often accompany life as an entertainer, but that doesn’t necessarily mean Wrestling With Depression is a dark show. The host’s quick wit and disarming self-awareness make for great company, and his guests always arrive at the mic with compelling stories to tell. From time to time the show even takes a “depression-cation” so Marty and a guest can nerd out on professional wrestling. It’s easily one of the most hilarious podcasts about depression, which means it’s also one of the best.

Third Coast Podcast

The Third Coast International Audio Festival has two goals: Find interesting audio stories, and share them with as many humans as possible. The Third Coast podcast is a director’s cut of the Re:sound radio show that airs Saturdays at 1pm on WBEZ. Think of it as a democratized version of This American Life. The producers gather music, documentaries and found sound clips and “remix” them into a sometimes strange, always compelling audio collage. Recent show themes have included the inner ear, babysitting and whodunnits. It’s unlike anything you’ve ever heard, and that’s totally the point.

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