Chicago Pub Crawls

Chicago Pub Crawls   Chicago Trolley Bachelorette Party

Chicago is one of the best bar towns in the world, and nothing beats a Chicago Trolley pub crawl to experience all the different neighborhoods and types of watering holes the Windy City has to offer.

Note: These are do-it-yourself crawls each with up to 10-12 pubs listed for completeness, which is probably more than anyone but only the heartiest of pub crawlers can handle, so feel free to customize each pub crawl to your abilities and tastes. Also, many crawls listed here feature pubs located beyond walking distance. Because driving and taking cabs are out of the question, the use of Chicago Trolley is highly recommended, particularly because you can bring your own beer! If you buy a copy of our book Historic Bars of Chicago ($12), you can get a $45 coupon that is more than 10% off for most rentals.

Pub Crawl
Chicago Trolley
By Seasonal Theme:



Chicago Trolley & Double Decker Co.


To book a trolley, contact Chicago Trolley for pricing &
availability at (773) 648-5000 or


These are do-it-yourself pub crawls. The agenda is
completely up to you.



By Sampling of Neighborhoods: