Headout logo. Link to home.
Pub Crawls

Historic Chicago Pub Crawl


    • Take in a grand experiencing of the amazing architecture, food, wine & Chicago’s incredible entertainment history
    • Learn about the Prohibition-era Chicago, jazz, theatre, while staying indoors using photos and videos on a shared iPad
    • Ideal for the solo traveller looking for a fun day, for couples looking for a great hangout and for groups looking for an exciting weekend
    • Its very little walking, it’s more of everything else; fun, food, & drinks
    • Tour encompasses Chicago Underground, a 19th century mansion, Tribune Tower, Michael Jordan’s Steakhouse, amongst other icons of Chicago’s entertainment history


    • Tour access
    • Select appetizers


    • Hotel pick-up & drop-off
    • Gratuities (optional)
    • Beverages

    Cancellation policy

    These tickets can't be cancelled or rescheduled.

    This tour is a mix of Chicago’s entertainment history, splendid food & drinks and the incredible architecture. Minimal walking and maximum education about the culture and history of everything that represents the Windy City.

    Your booking confirmation will be emailed to you within 20 minutes of purchase. Please display the same on your mobile phone at the venue.

    Missing any information?

    World at your tap.

    Get the Headout app to get tickets on your phone and access app-only deals. Talk about win-win.

    We've served 20 million+ guests and we are here for you

    20 million +

    Happy customers across 10,000+ experiences


    5,000+ verified reviews with 90% excellent score

    In the Media

    Featured and recommended by the best brands

    24 x 7 Help Center

    Have a question? Live chat with local experts anywhere, anytime