1.Private Speakeasy Pub Crawl in Chicago with Local Historian

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

Private 3-hour Chicago speakeasy crawl with a local historian, hotel pickup, secret entrances, and Prohibition-era cocktail stops. Drinks extra.

“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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2.Chicago Hidden Gem: Mid-Century Cocktail Bars Walking Tour

★★★★★★★★★★5.0 · 2 reviews · 1 hour 30 minutes (approx.) · from $51Top rated

Explore three mid-century cocktail bars in Ukrainian Village with water included, one cover charge included, and live music at the final stop.

“This is a great way to experience a less touristy Chicago neighborhood. Real bars with history and hanging out with the locals! We went to 3 bars in two neighborhoods - lots of different drinks is to try and options to dance if you want to stay later. Ronaldo is a great guide and fun to hang out with as well!”

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3.NOT OPERATING Walking tour to Chicago dive bars

★★★★★★★★★★5.0 · 2 reviews · from $45Best value

Walk Chicago’s West Loop drinking culture on a 2.5-hour small-group tour with five classic bars, local stories, and on-your-own drinks.

“Awesome tour!!! If you want to feel like a local this is the tour for you!! Vince was a great guide. Full of great tips”

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