In this episode of The Insomnia Project, a relaxing sleep podcast for insomnia, Marco and Amanda settle into a calm conversation about their recent trip to Chicago—“My Kind of Town.” As always, the discussion unfolds at an easy, unhurried pace, gently wandering through travel memories, city nicknames, architecture, and a few curious bits of Chicago lore.

The hosts begin by reflecting on the many nicknames Chicago has gathered over the years, from the famous Windy City and Second City to more unusual titles like City of Big Shoulders, Chiberia, The City that Works, and even Paris on the Prairie. Marco and Amanda enjoy exploring the personality behind these names and what they reveal about the city’s character and history.

Their conversation drifts into memorable sights from their visit, including the striking sculpture affectionately known as the Chicago Bean, the fascinating architectural boat tours that reveal the city’s skyline from the river, and their admiration for Jeanne Gang’s St. Regis Chicago, a building that left a lasting impression.

Along the way, they share stories about the curious legend of the “Phoenix Cow rising from the acid”, reflect on department store names that seem to carry possessive endings, and offer a small tribute to the elegant design legacy of Elsa Peretti. Naturally, no Insomnia Project travel conversation would be complete without a few food memories, and Marco and Amanda also mention some memorable Chicago spots they enjoyed along the way.

Like all episodes of The Insomnia Project, this softly spoken conversation is designed to help quiet racing thoughts and create a peaceful atmosphere for bedtime listening. Whether you’re dreaming of future travel, remembering past adventures, or simply looking for a relaxing podcast to help you fall asleep, this gentle Chicago journey offers a calm place for your mind to wander.

And we’re curious—which Chicago nickname is your favourite?

Chicago’s many nicknames include:

• Windy City

• Second City

• Chi-Town

• City of Big Shoulders

• Chiberia

• City in a Garden

• Great Commercial Tree

• Mud City

• City by the Lake

• The City that Works

• Heart of America

• The Great American City

• The City Beautiful

• The 312

• Paris on the Prairie

Resources mentioned in this episode:

• Sienna Tavern

• Harry Caray’s

• The Twin Anchor Pub

If this episode helped you relax, consider sharing The Insomnia Project, our award-winning sleep podcast, with someone who might enjoy a calm conversation before bed.

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