We're here to help
    Book online or call (650) 414-7338
    1. Local experiences/
    2. Chicago, IL/
    3. Transportation Tours/
    4. Bus Van and Limo Tours/
    5. Chicago's Original Gangster Tour
    Why travelers choose Greetwell
    Curated by our team

    Every experience is selected and approved for quality and safety

    Personal concierge

    Real humans available to help before, during, and after your booking

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else

    Easy booking

    Reserve in minutes with flexible cancellation on most experiences

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners

    Concierge Support

    • Help Center
    • (650) 414-7338
    • Contact our team

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Product image 4
    Product image 5
    Product image 6
    Product image 7
    Product image 8
    Product image 9
    Product image 10
    Product image 11
    Product image 12
    Product image 13
    Product image 14
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Chicago's Original Gangster Tour

    Experience Chicago as it was during the 1920s and 1930s!

    From$53

    Search all experiences

    Discover what we've curated for you

    Duration

    1 hr 40 mins–2 hrs

    Includes

    Guided bus tour, Actor guides

    Highlights

    Explore Chicago’s Prohibition past on a narrated bus tour led by actor Gangster Guides. Hear true stories of Capone, Moran, and Dillinger as you pass infamous landmarks.

    • Visit sites like the St. Valentine’s Day Massacre location and the Biograph Theatre
    • See the Holy Name Cathedral and other notable stops
    • Ride a bus for the entire tour
    • Enjoy entertaining, historically accurate narration
    • Learn about Chicago’s 1920s and 1930s underworld

    What's Included

    • Guided bus tour
    • Live narration by actor Gangster Guides

    Things to know

    Guests remain on the bus for the duration of the tour. Please arrive 10–15 minutes before your scheduled time; tours depart promptly. No coolers, alcohol or food are allowed; non-alcoholic beverages with lids are welcome.

    FAQs

    Where is the meeting point?
    Meet at the intersection of Clark & Ohio (600 North Clark Street), on the Clark Street curb in front of the McDonald’s.

    How long is the tour?
    The tour lasts 1 hour 40 minutes to 2 hours, and guests remain on the bus for the duration.

    Can I bring food or drinks?
    No coolers, alcohol or food are allowed on the bus. Non-alcoholic beverages with a lid are welcome.

    Is public transit nearby?
    The pickup is within 4 blocks of the Red Line Grand stop and within 2 blocks of the 22 Bus Huron or Grand stops.

    Is parking available?
    Several garages are within walking distance; plan extra time as tours leave promptly at the top of the hour.

    Cancellation policy

    All sales are final. No refunds, adjustments, or exchanges. All tours depart at the scheduled time.

    Meeting location

    We will meet at the intersection of Clark & Ohio (600 North Clark Street). Please stand on the Clark Street curb of the large McDonald's.

    Experience provided by Untouchable Tours
    Experience provided by Untouchable Tours

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Reference #GP6TVZ

    Guest

    $53.55

    0

    Why book through Greetwell?

    • Greetwell Approved

      This experience meets our quality and safety standards

    • Includes Concierge Support

      Our team is here to help with questions, timing, or special requests

    • Flexible Cancellation

      Plans change? Most experiences offer flexible cancellation

    4.6 stars• 348 reviews

    Nearby activities

    Thumbnail

    Chicago Winery Tour and Tasting

    From$52/ person
    Thumbnail

    New Orleans Historic Donut & Beignet Tour

    From$68/ person
    Thumbnail

    West LA Donut Walking Tour

    From$68/ person
    Thumbnail

    Washington DC Historic Donut Tour

    From$68/ person
    Thumbnail

    Miami: Wynwood Art, Culture, & Donut Tour

    From$68/ person
    Thumbnail

    Miami South Beach Donuts, Pastelitos & Patisserie Tour

    From$68/ person