Tour Guide

WANTED: MOBSTER TOUR GUIDES IN CHICAGO!

Step into the shoes of a 1920s gangster (minus the crime!) and bring the Windy City’s notorious past to life — all in broad daylight.

If you’ve got a flair for storytelling, love true crime, and want to show off Chicago in the most killer way possible, we’ve got the perfect gig for you.

• Lead daytime walking tours through the streets once ruled by Capone & company
• Spin tales of heists, speakeasies, and mob drama that made headlines
• Make history fun, fascinating, and unforgettable for guests from all over
• Rock a fedora (optional, but highly encouraged)

• $50 per tour (plus potential tips from impressed guests!)
• Consistent daytime shifts – perfect for actors, history lovers, & freelancers
• Free & discounted tours for your family and friends nationwide
• Flexible part-time hours

Downtown Chicago, IL – The OG stomping grounds of America’s most infamous mobsters.

• Natural performers, history geeks, and true crime junkies
• Confident public speakers who can own the sidewalk
• Reliable locals within 25 miles of downtown Chicago
• Folks who are energized, entertaining, and love engaging with a crowd

• Apply using the link below
• We’ll reach out to schedule a quick intro call
• Shadow a tour to see how it’s done
• Then… it’s lights, camera, MOBSTERS.

Watch our quick behind-the-scenes video: [Insert Link]

Make your mark on Chicago’s streets (in a totally legal way).

Step into history. Tell the stories that shaped the city.

Apply now and make daytime feel dangerous — in the best way.