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Dark Hollywood in Chicago



1.25 mi.

90 min

Returns Spring 2024


Uncover Hollywood's sinister past in Chicago through The Wizard of Oz, "cocaine movies," and gangsters

A park inspired by The Wizard of Oz, homes designed by Chicago's leading architect, and a theater built for moving pictures seem friendly enough. But a closer look at these three Chicago locations leads us down a destructive path closely tied to Hollywood.

Join Chicago Movie Tours in Chicago's Lincoln Park neighborhood for a 90-minute guided outdoor walking tour on the darker side of the silver screen.



You'll start the tour in a neighborhood park devoted to The Wizard of Oz. Here, you'll learn about Chicago's connections to the beloved children's story. But also, brace yourself for untold, darker tales behind the iconic 1939 movie that will leave you shocked.

Your adventure continues as you stroll down a tree-lined street, surrounded by houses with a rich history that whispers secrets of Hollywood's scandalous silent era. Uncover the intriguing connections to "cocaine comedies" as you explore these architectural gems with our expert tour guide.

From there, you'll follow a narrow brick road. It's not yellow, alas. But look carefully as you walk, and you'll find written remnants of Chicago's past. 

On the final stretch, your tour takes a thrilling turn into the heart of Chicago's notorious gangster history, seamlessly interwoven with the glamour of Hollywood's golden era. It's a story that will captivate you, leaving you with a deeper understanding of the city's enthralling—and disturbing—past.

Don't miss your chance to be part of this adventure in Chicago. Book your spot now!

Private Tours

Private Tours

Yes, you may book this tour as a private or group tour!

The private tour price listed below is a flat fee for up to 10 guests. If you have more than 10 in your party, please contact us so we can accommodate you.

Tour Specifics

Start/End Points

The tour starts at Oz Park, 2021 N Burling St. next to the Tin Man sculpture (W. Webster/N. Larrabee). The tour ends at 2433 N Lincoln Ave.


Guests must initial a digital general waiver of liability with Chicago Movie Tours when they book. 


If available, free parking spots run along the residential streets near Oz Park. Public transit: take the Brown Line or Purple Line to Armitage, or take the Brown, Purple, or Red Line to Fullerton. Our starting point is a 0.4 mile-walk from the Armitage 'L' station and a 0.5-mile walk from the Fullerton 'L' station.


All of our stops on the walking tour have sidewalks and crosswalks. We will travel down an original brick-paved road.

What to Bring

Please wear weather-appropriate clothing. Tours run rain or shine.


A Target store with a public restroom is near the start of our tour route.


While this tour explores the children's story The Wizard of Oz, some content may not be appropriate for guests under age 13.


No video or audio recording of the tour, but take as many pictures as you'd like!

Cancellations and Refunds

You may cancel or amend your reservation 48 hours or more before the tour departs. Read more Tour Terms and Conditions.

Movies/TV Highlighted
  • Public Enemies (2009)

  • High Fidelity (2000)

  • The Lady in Red (1979)

  • The Wizard of Oz (1939)

  • Get Out and Get Under (1920)

  • The Mystery of the Leaping Fish (1916)

  • For His Son (1912)

  • The Wonderful Wizard of Oz (1910)

Returns Spring 2024


What's Included

  • Expert tour guide commentary, including little-known facts and stories from Hollywood's and Chicago's pasts

  • Visual and audio media to enhance your experience

  • Plenty of Instagram opportunities 

  • Mini goodie bags!


Todd Miller
average rating is 5 out of 5

November 11, 2023

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Best Chicago tour I’ve been on. Don’t miss it!!
average rating is 5 out of 5

October 15, 2023

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Kelli was great! Very knowledgeable, and the Dark Hollywood tour was fun, interesting, and everything discussed was tied together in some way.
average rating is 5 out of 5

November 1, 2023

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So glad I made the decision to attend my first tour with Chicago Movie Tours (Dark Hollywood in Chicago at Oz Park). The tour was fun and interactive. Kelli did a fantastic job of presenting and leading! She was a joy! Different mediums were used (book, photo, video, examining statues on the tour, & stories) to share history and movie knowledge. I learned a lot of information that I’ve been excited to share with others! Kelli did a wonderful job bringing Chicago and (multiple) movies together on this tour. Looking forward to attending more tours!
Robert Bender
average rating is 5 out of 5

October 15, 2023

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The tour is a fantastic dive into the production of The Wizard Of Oz and the toll the cocaine movement took on famous early twentieth-century Hollywood film stars. For those who like the dark details, the tour dispels many myths and discloses secrets hidden behind the studio's production of The Wizard Of Oz, and it exposes the dark backdrop that makes the movie such a vivid Technicolor success to audiences.
average rating is 5 out of 5

October 29, 2023

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An enjoyable afternoon was spent in Chicago's Oz Park and I learned many fun facts about the close tie between the beloved Wizard of Oz movie and Chicago. Kelli was a fantastic tour leader - would recommend her on any tour she leads!

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Chicago Movie Tours gift cards are valid for any listed walking tours, virtual tours, courses, or merchandise.

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