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July 3, 2025

Is Chicago the Best Summer City in the US?

City Cast Chicago

Is Chicago the Best Summer City in the US?

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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!

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