The 3 Pub Crawls in Chicago to Book First

1 tours

The city has 1 pub crawls on offer and these 3 are the ones that hold up. Prices, durations and the details that matter are below, so you can choose in five minutes and get on with the rest of the trip.

Chicago Cocktail & Speakeasy Tours, Chicago Gangster & Prohibition Tours, Chicago Tours, Drinking Tours, Nightlife, Private, Pub Crawls, Tour Reviews

Private Speakeasy Pub Crawl in Chicago with Local Historian

1.Private Speakeasy Pub Crawl in Chicago with Local Historian

★★★★★★★★★★4.5 · 5 reviews · from $101Our pick

A private 1920s Chicago speakeasy crawl with a historian, secret entrances, hotel pickup, and period-style cocktails for you to choose.

“I booked this speakeasy tour for a joint bachelor / bachelorette party I was hosting and it was wonderful! Our tour guide, Conor, picked great places to accommodate our group of 16. He and our driver, Melvin, showed up 15 minutes early and kept us on track all day, they even made sure we could get a group photo with a good view of the city. Conor made the whole experience very easy and memorable.”

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August 11, 2026