Where to Go Out: the 8 Best Chicago Bar Crawls

1.Chicago River: Guided Sunset Cocktail & Architecture Tour

★★★★★★★★★★4.6 · 203 reviews · 1h 30m · from $68Our pick

Spend 90 minutes cruising the Chicago River at dusk while an English-speaking guide explains more than 50 buildings, from Art Deco towers to modern skyscrapers. Your ticket includes one or two drinks, depending on the option selected, plus coffee, soda, and bottled water. Bring layers, and find the boat at the final dock.

“Fun trip, excellent, knowledgeable guide. Good drinks. Friendly staff. Accommodating to my unexpected schedule change. Crowded and fairly small boat, but still I would highly recommend.”

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2.Chicago River Cocktail Cruise

★★★★★★★★★★4.5 · 86 reviews · from $49

You’ll spend 90 minutes cruising Chicago’s river past more than 50 notable buildings, including the Wrigley Building, Michigan Avenue Bridge, and Magnificent Mile. Choose a package with one or two alcoholic drinks, then listen to guides such as Justine, Brian, Jim, or Ed explain the city’s architecture. The boat has a restroom, snacks, coffee, tea, soda, and water.

“A Fun way to see Chicago and learn a little history and architecture, with booze as an extra incentive.”

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3.Tiki Bar Cruise on Chicago River or Lake Michigan

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

Board Island Party Boat at Dock 12 for a 75-minute tiki-themed cruise along Chicago’s main, North, and South river branches, or out on Lake Michigan. Expect palm trees, thatch roofing, music, climate control, restrooms, and a full bar where drinks cost extra. It suits relaxed afternoons, celebrations, and post-sightseeing downtime.

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4.Vito’s Vault Chicago finest dinner theatre speakeasy

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

At Vito’s Vault, you enter a 1929 speakeasy at 5901 W Lawrence Ave, give the password, enjoy dinner and homemade hooch, then watch a 90-minute musical revue. Vito and his gang stay in character as servers and performers, mixing songs, dancing, comedy, and audience participation into a three-hour evening.

“Wonderful experience! Friendly, welcoming, and a lot of fun. Food was good and show was fantastic. Service was very good and wait staff were very personable.”

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5.3-Hour Private Speakeasy Cocktail VIP Tour

★★★★★★★★★★5.0 · 7 reviews · 3 hours

Spend three hours with a private historian guide visiting three or four working Chicago speakeasies. Enter through secret passages, hear stories of bootlegging and gangsters, and travel between stops in a Mercedes, Cadillac, or luxury coach. Drinks cost extra, and the tour is for adults 21 and older.

“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 speakeasies with a private historian and driver. Enter through secret doors, hear stories of Al Capone and bootlegging, and order Prohibition-era drinks at your own cost. Guides such as Conor, Stefan, and Kai have led groups, and hotel or port pickup is included.

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

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

Meet Ronaldo at 8 p.m. for a 90-minute walk through Chicago’s Ukrainian Village and nearby streets. Visit three hard-to-find bars for craft cocktails, beer, non-alcoholic drinks, music, and local stories. Drinks and food cost extra, but water and the final bar’s cover charge are included. The group is limited to 16 people.

“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 visits five West Loop taverns and pubs in about 2.5 hours. A guide such as Vince leads groups of up to 12, with 30 minutes at each stop and drinks and snacks purchased separately. Note that this experience 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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