Dreaming of a city escape that blends world-famous architecture, lakefront beauty, rich history, and dynamic culture? Chicago has it all. From iconic skyscrapers to hidden neighborhood gems, this episode will change the way you see the Windy City.

Today host Angie Orth welcomes Kit Bernardi, a Chicago native and travel journalist, on the rooftop of the Virgin Hotel in Chicago. She’ll reveal the stories and experiences that make her hometown shine, from the Great Fire that reshaped the city to the immigrant roots that continue to define it. Kit shares insider insights that go far beyond the guidebooks.

You’ll hear about the best ways to see Chicago’s legendary skyline, when to hit the lakefront for outdoor adventures, where to explore can’t-miss museums and theaters, and how to begin a Route 66 journey. Whether you’re planning your first trip or a repeat visit, this episode is packed with tips that will help you experience Chicago like a local.

What You’ll Learn:

05:32 How the Great Chicago Fire reshaped the city

12:27 Must-see museums and surprising niche gems

15:49 Chicago’s thriving theater scene

17:53 Sports culture and the “no ketchup” hot dog rule

19:23 Starting Route 66 the classic way

Connect with Kit Bernardi:

Website: https://kittravels.com/

Instagram: https://www.instagram.com/kitbernardi/

More of Kit’s Chicago Recommendations: 

Neighborhoods to Visit: Hyde Park, Oak Park, Pilsen 

Attractions: Chicago Cultural Center, Chicago Sports Museum, National Museum of Mexican Art, DuSable Black History Museum and Education Center, The American Writers Museum, Chicago History Museum, Jane Addams Hull House Museum 

CTA: What’s your favorite must-see in Chicago? Tell us about it in the comments! 

Connect with AAA:

Book travel: https://aaa-text.co/travelingwithaaa 

LinkedIn: https://www.linkedin.com/company/aaa-auto-club-enterprises

Instagram: https://www.instagram.com/AAAAutoClubEnterprises

Facebook: https://www.facebook.com/AAAAutoClubEnterprises