Hidden History in Chicago's Gold Coast
About the Tour
Amy Bizzarri, author of 111 Places in Chicago That You Must Not Miss, takes you on a fascinating guided tour of hidden historical spots in Chicago's gilded Gold Coast. Peep behind the gates of the original Playboy Mansion, walk along a wooden block-paved alley, sip a Faster Pussycat in Chicago's oldest piano bar and more as you enjoy a delightful walk through time in this exclusive Chicago neighborhood.
Tour Producer
Amy Bizzarri
I’m Amy Bizzarri, a Chicago-based storyteller and educator. I'm also an armchair historian, PADI-certified scuba diver, yogini (and certified yoga instructor), mom, and mermaid (proud graduate of Weeki Wachee Mermaid School), not necessarily in that order.
My deep Chicago roots trace back to an extraordinary family legend: my great‑great‑grandparents met on the night of the Great Chicago Fire, when volunteer firefighter Walter Daker mistook young Catherine’s flowing ginger hair for flames and swept her up in his arms, literally and figuratively. I'm the author of a few Chicago history‑focused books, including Discovering Vintage Chicago, Chicago’s Iconic Dishes, Drinks, and Desserts, and 111 Places in Chicago That You Must Not Miss. I live in a century‑old home in the Logan Square neighborhood.
In my 20s, I lived in Italy, where my family has roots (Felina, RE). I'm an expert in all things Italy.
I speak fluent Italian and French; excellent Spanish and Portuguese.
My love for wine led me to pursue Wine and Spirt Education Trust (WSET) sommelier certification, levels 1-3.
I love a great road trip, too. So much so that my book The Best Hits on Route 66 earned the 2019 Silver Lowell Thomas Award for Best Travel Guide from the Society of American Travel Writers. I followed that bestselling guide with The Best Hits on the Blues Highway, which explores U.S. Route 61, the storied road that shaped American music. My latest book, Route 66 Recipes, celebrates the history behind the diners, dives, and restaurants along the Mother Road as it approaches its 100th anniversary in 2026.
1,000s of children have passed through my classroom doors over the years. I'm a dedicated educator with over 20 years of experience, holding a Master of Arts in Education with a focus on bilingual education. I'm Reading Apprenticeship and International Baccalaureate-certified, endorsed in ESL, and I've been awarded several study grants from the National Endowment for the Humanities (2019, 2021, 2022, 2023).
My storytelling has expanded beyond the page: I've hosted local and national television/radio segments, and I've produced interactive smart walking tours with VoiceMap and EAtlas.
Follow my adventures on Instagram at Instagram.com/amybizzarri to see where in the world I am today!
Preview Location
Location 16
Playboy Mansion
This 70-room classical French brick and limestone home was originally built in 1899 for Dr. George Swift Isham. He was a... Read More
How VoiceMap Works
Major Landmarks
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International Museum of Surgical Science
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Original Playboy Mansion
Getting There
Route Overview
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Start location1601 N Clark St, Chicago, IL 60614, USA -
Total distance2km -
Distance back to start location866.34m
Directions to Starting Point
The starting point is the Chicago History Museum, located at 1601 N. Clark Street. The Museum is easy to reach via public transportation. CTA buses 22, 36, 72, 73, 151, and 156 stop nearby. The Brown Line Sedgwick station and Red Line Clark/Division station are approximately one half-mile from the Museum.
For more information, visit transitchicago.com
Tips
Places to stop along the way
Couch Mausoleum, International Museum of Surgical Science, Wooden Block Alley, Playboy Mansion, 3 Arts Club Courtyard, Pump Room, Zebra Lounge
Best time of day
Daytime, 10am - 4pm.
Precautions
The area safe, but always be aware and street smart.
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