Day Tour Guide
Chicago, IL
Part Time
Student (High School)
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.
WHAT YOU’LL DO (LEGALLY):
PAY & PERKS:
LOCATION:
Downtown Chicago, IL – The OG stomping grounds of America’s most infamous mobsters.
WHO WE’RE LOOKING FOR:
NEXT STEPS TO JOIN THE CREW:
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.
Wanna see what you’re getting into? 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.
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.
WHAT YOU’LL DO (LEGALLY):- 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)
PAY & PERKS:- $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
LOCATION:Downtown Chicago, IL – The OG stomping grounds of America’s most infamous mobsters.
WHO WE’RE LOOKING FOR:- 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
NEXT STEPS TO JOIN THE CREW: 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. Wanna see what you’re getting into? 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. Apply for this position
Required*