Jacoby Cochran and all 12 other City Cast podcast hosts (from Austin, Boise, DC, Denver, Houston, Las Vegas, Madison, Nashville, Philly, Pittsburgh, Portland, and Salt Lake City) compete head-to-head in a high-stakes showdown to answer the question that’s been burning up our company-wide Slack for weeks: which city is the best for a summer weekend trip? From naked bike rides to ‘the country’s best farmers market,’ pickle festivals to Elvis impersonators driving pink convertibles, our hosts are bringing the best of the best of what their city has to offer. Did your city win?

Take our interactive quiz to see which city best fits YOUR vibe!

Between Fourth of July weekend, Windy City Smokeout, and the number of cookouts we’re seeing at the park, it’s prime barbeque season in Chicago. Host Jacoby Cochran and Chicago magazine dining critic John Kessler talk about some of the city’s best spots to pick up BBQ, what makes Chicago’s style unique, and some tips for home pitmasters.

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Once the fireworks and NASCAR engines die down, there’s still going to be plenty to do in July in Chicago. That’s why host Jacoby Cochran, executive producer Simone Alicea, and digital creator Paige Serena are here with their best monthly tips, including summer pop-ups to check out and new laws going into effect.

If you're new here, welcome! We’ve put together a starter pack for you, with episodes and articles to welcome you to the City Cast Chicago community.

For even more tips on how to make the most of June in Chicago, check out Hey Chicago’s take on what to do this month.

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Gov. JB Pritzker announced he’s running for a third term as governor. But that hasn’t exactly put a stop to presidential speculation. Host Jacoby Cochran and executive producer Simone Alicea explain why and discuss how the 2026 election landscape is shaping up in Illinois. Plus, they cover a comprehensive ice cream map and offer some additional neighbor shoutouts.

Good news: Winnemac Park Fourth for All

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Last weekend’s Black Yacht Weekend brought thousands of visitors to the city and Lake Michigan for dozens of events in and out of the water. Unfortunately, between tragic accidents, oversold events, and mixed reviews, it’s hard to know if the weekend was a real success. WCIU TV host Brandon Pope and Block Club Chicago’s Maxwell Evans are here to recap. Plus, we’re discussing the future of two of the city’s largest shelters, exciting news for the first South Side birthing center, and Marvel’s Ironheart landing in Chicago!    

Good News: Food Truck Festival, Art of Sole 2, Margarita Festival 

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Summer is here, which means we’re outside — not just on the beach, but in the club, too. That’s why we’re revisiting our conversation from the fall with CaSera Heining, aka DJ Ca$h Era. As one of the busiest DJs in Chicago, Ca$h Era gives us the scoop on some of the best parties and spots, tips for building a set list, and when it’s okay to request a song from the booth.

Spots mentioned:

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The fourth season of “The Bear” drops today on Hulu. Not only has the show about an Italian-beef stand-turned-fancy restaurant garnered awards year after year, but it has also become a fixture of Chicago discourse. But be honest … are we kind of over it? Newsletter editor Emmi Mack and social media manager Rick Homuth are certainly skeptical, but host Jacoby Cochran and executive producer Simone Alicea are still fans. They offer their hot takes and season four predictions.

Good news: The Spades Table

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Chicago’s extreme heat warning has finally ended after record temperatures for June. The City Cast Chicago team recaps the weekend and also discusses the 30-year anniversary of Chicago’s deadliest heat wave. Plus, Mayor Johnson vetoes snap curfew ordinance, and Montrose Beach welcomes newest piping plovers!

Good News: Respect the Mic

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Summer in Chicago means more street festivals, more time by the water, and the return of 16-inch softball leagues across the city. Host Jacoby Cochran recently joined the KUP Media Softball League at Mozart Park. The City Cast team recently caught a game and learned more about this nearly 140-year-old Chicago pastime from Axios reporter and league member Justin Kaufmann.

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City Cast hosts are on the pulse of what’s happening in our communities. So Jacoby Cochran and all 12 other hosts sat down with City Cast CEO David Plotz to talk about creative local problem solving that might work in your hometown too and to commiserate about stressors affecting most of our cities, from unaffordable housing to bike lanes.

Learn more about the sponsors of this June 20th episode:

Babbel - Get up to 60% off at Babbel.com/CITYCAST