Best Chicago Bar Tours — Our Top 8

1.Prohibition Speakeasies Bus Tour or Walking Tour

★★★★★★★★★★4.8 · 168 reviews · 3 - 4 hours · from $47Our pick

Choose a downtown walking tour or neighborhood bus tour with guide Jonathan Knotek. Visit three or four historic speakeasies, hear Chicago gangster and high-society stories, and get drink suggestions tied to the Prohibition era. Bring ID and money for drinks.

“We had so much fun and learned so much about Chicago’s speakeasy and mob scene! Our tour guide was laid back and great, very knowledgeable. We had great drinks along the way from 3 very different places. We enjoyed the whole 3 hours very much and would definitely do it again. Highly recommend!!”

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2.Tiki Bar Cruise on Chicago River or Lake Michigan

★★★★★★★★★★3.8 · 16 reviews · 1h 15m · from $41Best value

You’ll cruise from Dock 12 aboard a tiki-themed boat with palm trees, thatch roofing, music, a climate-controlled lounge, restrooms, and a full bar. The 75-minute route may cover Chicago’s river branches or Lake Michigan. Drinks cost extra, and staff speak English.

“It’s a nice ride but the bottom level smelled really bad like moldy carpet. Staff was cool and they offer an open bar option. I was also add better music if there is no tour guide.”

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3.Vito’s Vault Chicago finest dinner theatre speakeasy

★★★★★★★★★★5.0 · 14 reviews · 3 hours (approx.) · from $88Top rated

At Vito’s Vault, you give the password, enjoy a full dinner, sample Vito’s homemade hooch, and watch a 90-minute musical revue of 1920s songs, dancing, comedy, and audience participation. The 3-hour evening begins at 6:00 pm in a small speakeasy-style venue with free parking.

“Absolutely brilliant evening! Vito and the team put on a fantastic night. A small, intimate speakeasy-style bar and restaurant with stunning 1920s-inspired décor. Dinner was delicious, and the service was excellent. The show was outstanding — a perfect mix of amazing singing, lively dancing, and plenty of laughs! Huge thanks to Vito and the team for such a wonderful experience that we both thoroughly enjoyed. Just don’t forget the password 😉 Stephen 🇬🇧”

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4.Walking Tour: Historic Chicago Pubs in River North and the Loop

★★★★★★★★★★5.0 · 9 reviews · from $65

Join a guide such as Tom for a 3.5-hour, small-group walk from the Marquette Building to Monk’s Pub. Visit four beloved Chicago taverns, hear stories about architecture, media, bribery, and Prohibition, and pay for your own drinks and food.

“This is a great tour! It has a little of everything - architecture, skyscraper history, pubs, the L, stories, pubs, nice views, oh, and pubs! The tour guide had tons of great information and fun stories.”

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5.3-Hour Private Speakeasy Cocktail VIP Tour

★★★★★★★★★★5.0 · 7 reviews · 3 hours

Spend three hours with a private guide visiting three or four working Chicago speakeasies. Enter through secret passages, hear gangster-era stories, buy period-style cocktails, and ride between stops in luxury transport with hotel pickup inside Chicago.

“Alan, our host, was knowledgeable, kind and funny. He took us to great spots and made everything so fun. It was a huge hit with my group.”

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6.Private Speakeasy Pub Crawl in Chicago with Local Historian

★★★★★★★★★★4.5 · 5 reviews · from $101

Spend three hours visiting historic Chicago bars with a private guide such as Conor, Stefan, or Kai. Enter through secret doors, hear stories of Al Capone and bootlegging, and order period cocktails at your own cost. Hotel pickup, drop-off, bottled water, and private transport are included.

“At $330/person I was surprised that the operator/guide did not provide the drinks at the bars. He was very knowledgeable about the city and we had a great time. It was just too expensive.”

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

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

Join Ronaldo at 8 p.m. for a 90-minute walk through Ukrainian Village and nearby streets, stopping at three hard-to-find bars. Buy your own drinks, enjoy water and local stories, then finish with live music, dancing options, and a 1930s lounge feel.

“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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8.NOT OPERATING Walking tour to Chicago dive bars

★★★★★★★★★★5.0 · 2 reviews · from $45

This evening walking tour takes you through Chicago’s West Loop to five long-running taverns, pubs, and neighborhood bars. Groups are capped at 12, with about 30 minutes at each stop and 10 to 15 minutes between them. Guide Vince is specifically praised for useful local tips. The tour is currently not operating.

“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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