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This week on the Curious City podcast we dig back into the archives to share one of our favorite stories about the song made famous by Frank Sinatra, “Chicago (That Toddling Town).” The song pays homage to the partying and excess of the roaring 20’s during Prohibition. It also contains a lyric about a man who tried to save the soul of Chicago. Who was he and how did he end up in the song? Plus, we hear from several small businesses about what they’ve been doing to keep their businesses going- and some of the lessons they’ve learned along the way.

Though little known on the North Side of Chicago, the sweet steak has been attracting long lines of fans to South Side eateries for 50 years now. The sandwich starts with a steamed bun, piled high with grilled onions, chopped ribeye steak, American cheese, sweet pepper relish, sliced tomatoes and hot peppers — all doused in a signature reddish sweet sauce. Curious City’s Monica Eng digs into the origins of the sandwich and what’s in store for the future. Hint: it has to do with walnuts.

One Curious Citizen wanted to know what people who moved to Chicago love about the city. From fireflies to the way people walk, we hear what transplants say makes Chicago so special. Plus Curious City’s Monica Eng helps answer a question from another Chicagoan who's frustrated that the city’s playgrounds are still closed while so many other restrictions are easing up.

Curious City took a road trip and counted almost a hundred billboard ads for lawyers along I-90/94 on the border between Illinois and Indiana. Audio producer Steven Jackson investigates why there’s so many of these billboards in this area, especially for personal injury attorneys. He shares insights from lawyers, marketers, and historians. (Features a cameo appearance from President Lyndon B. Johnson.)

Chicago winters can be long and brutal. Curious City’s Monica Eng spoke with postal workers and other Chicagoans who spend a lot of time outdoors about how they dress for warmth during the winter. Also, we hear from a listener who asks what happens to the colorful landscaping along Michigan Avenue during the winter months.

A listener wanted to know some practical things he could do to support struggling businesses. Monica Eng shares tips from industry experts on how to support small businesses like bookstores and music venues. She also talks with chef Beverly Kim about how female restaurateurs in Chicago have been supporting one another during the pandemic.