Historic Chicago Pub Crawl Chicago | Tickets, Tours & Deals | Headout
All Categories
Best Sellers
Download app
The world on your tap!Get the Headout app to get tickets on your phone and access app-only deals. Talk about win-win.

Historic Chicago Pub Crawl

Mobile Ticket
2 hrs 30 mins


  • 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

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.

my tickets

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

additional information

All guests must choose a beverage for the walking tour and bring cash to cover 2.5 servings of beer ($18), wine ($18), soda ($6) or water ($3)

Missing any information?
This experience is unavailable
You'll be the first to know when these tickets are back online.
notify me
Awesome!We will notify you.
Why Headout?
Trusted platform used by 100K+ people, each month
Get the lowest prices and last minute availability
Discover and connect with 10,000+ experiences
Browse verified reviews and professional photographs
Have a question? Live chat with our experts 24/7
The world on your tap!Get the Headout app to get tickets on your phone and access app-only deals. Talk about win-win.
We've served 9 million+ guests and we are here for you
9 million +Happy customers across 10,000+ experiences
4.4/55,000+ verified reviews with 90% excellent score
In the mediaFeatured and recommended by the best brands
24 x 7 help CenterHave a question? Live chat with local experts anywhere, anytime