holibob

Great choice — the Chicago: Mob Crime, Capone, Speakeasies, and Ghosts Walking Tour! 🌟 I've opened it up for you. Want the full details, to check your dates, or shall I show you similar things nearby?

Chicago: Mob Crime, Capone, Speakeasies, and Ghosts Walking Tour

Chicago: Mob Crime, Capone, Speakeasies, and Ghosts Walking Tour

5.0 (400) 🕑 1h 30m Free cancellation

Swap the standard Chicago itinerary for the chance to experience a whole different side to the city. Walk in the footsteps of Al Capone and John Dillinger while hearing tales of Chicago's haunted past. This walking tour takes you to prohibition-era speakeasies, sites of real life mob shootouts, and provides special access to places tied to historical events that have shaped Chicago.

Languages: English
📍238 N State St, Chicago, IL 60601, USA
🏢Operated by Magnifico Tours

Highlights

  • This walking tour brings one of America's most notorious eras to life
  • Benefit from your historian guide's rare insights into Chicago history
  • See parts of Chicago that most visitors miss
  • This compact tour leaves plenty of time for other activities

What you'll see & do

  • Our expert host will meet you at the starting point and begin to explain the architecture and haunted history along the Chicago River.
  • You will see historic buildings that operated as speakeasy bars of the Prohibition Era, and see famous spots connected to legendary bank robber John Dillinger.
  • Interact with the largest Picasso in the world as you learn about Chicago corruption, and the ghostly hauntings of the Chicago Theater District.
  • Go underground and explore the site of a famous 1920s gangster 'whack.' Learn about the exciting height of Prohibition gangster history, right where it happened.
  • Learn about the ghosts of the Art Institute, haunted hotels, and more paranormal activity around Chicago's biggest landmarks.
  • The tour ends a 5 minute walk from the start. Your host will end with incredible true crime stories, additional recommendations around Chicago, and will assist you with anything else you may need after your experience.

What's included

  • Expert Tour Guide
  • Go Inside Famous Hotels

What's not included

  • Tips and Gratuities for Tour Guide

Good to know

Wheelchair accessible

Infants and small children can ride in a pram or stroller

Service animals allowed

Public transportation options are available nearby

Transportation options are wheelchair accessible

All areas and surfaces are wheelchair accessible

Suitable for all physical fitness levels

This is a walking tour, 1.0 Miles over 1.5 Hours

Not recommended for travelers with a cold

Cancellation policy

  • A full refund will apply if you cancel more than 24 hours before the activity start time.
  • No refund is possible if you cancel less than 24 hours before the activity start time.
Free cancellation 🔒 Secure checkout
from
US$ 33.00

Your shortlist

🤍
Tap the heart on any experience to save it here.

Why book with Holibob?

470,000+ bookable experiences worldwide 🌍

We've spent over a decade connecting travellers with things to do, and we power experiences for travel brands across the globe.

  • 🔒 Secure checkout. Your card is encrypted and processed by Stripe — we never store it.
  • Free cancellation on most experiences. Look for the “Free cancellation” mark on your activity.
  • 🌍 Real local operators. Every experience is run by a vetted local guide, not a faceless reseller.

Need a hand?

Our bookings team is here to help:

holibobbookings@holibob.tech
+44 20 805 09518