Curious City

There’s no New York-land or Boston-land, so why does the Chicago metropolitan area have its own unique name?

It turns out this has been a question on the minds of many Curious City listeners. To learn more, we looked at the origins of this term, how its meaning has changed over time and the media mogul — or Colonel — behind it all.

This episode originally aired in 2023.

The stretch of beach that starts where DuSable Lake Shore Drive ends wasn’t always as vibrant or as ‘gay’ as it is today. Its transition was spearheaded by Jerry Marcoccia, who was searching for a sense of belonging in the 1990s. "You can't talk about this beach being gay without including me,” he said.

Comic Sans often signals levity or sarcasm. The font is occasionally used for a key phrase in some official city elevator inspection certificates. That’s caused concern for some Chicagoans, including at least two Curious City listeners.

A concentrated Filipino community area is not as easy to spot as neighborhoods like Chinatown or Little Village. In this episode, we’ll look at the long history Filipinos have had in Chicago stretching back to the early 1900s. We’ll also look at how Filipino restaurants have made a mark across the city in recent years, from Jefferson Park to Pilsen.

Originally published in February 2025.

Curious City listeners wondered if helicopters they heard buzzing around their Chicago neighborhoods at night were part of the federal government’s immigration enforcement. There is some truth to that, but it turns out odd helicopter flights have been a curiosity long before Midway Blitz.