7 Chicago Bar Tours Worth the Money

1.Chicago River: Guided Sunset Cocktail & Architecture Tour

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

Spend 90 minutes on the Chicago River as an English-speaking docent explains the design and history of more than 50 buildings. You’ll pass century-old bascule bridges and see downtown as daylight fades. Depending on your ticket option, one or two alcoholic drinks are included; coffee, soda, and bottled water are free.

“The tour was fantastic. Everyone was friendly, and the guide lady was very knowledgeable and attentive. I highly recommend it for first-timers in Chicago.”

Check availability →Read our full review

2.Chicago River Cocktail Cruise

★★★★★★★★★★4.5 · 86 reviews · from $49

Spend about 90 minutes on the Chicago River, passing more than 50 notable skyscrapers, the Wrigley Building, Michigan Avenue Bridge, and the Magnificent Mile. A live guide covers the city’s architecture and history while you relax aboard a boat with a restroom and bar. Drink packages vary, with one or two alcoholic drinks included in selected options.

“Just being on the water and here in Chicano with my sister and daughter was great. Bbbbbbbbbbbbbbbbbbbbbbbbbbnnnbnnbbbnmkjhs do I it d go ok j J F x”

Check availability →Read our full review

3.Tiki Bar Cruise on Chicago River or Lake Michigan

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

Settle into a tiki-themed boat with palm trees and thatch roofing for a 75-minute Chicago cruise. The route covers the river’s North, South, and main branches, with skyline views, music, a climate-controlled lounge, restrooms, and drinks for purchase. The boat starts and ends at Dock 12. An English-speaking host or greeter is listed, but guided commentary is not specified.

“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.”

Check availability →Read our full review

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-inspired Chicago speakeasy by giving the password, then enjoy dinner and a lively 90-minute revue of twenties songs, dancing, comedy, and audience participation. The roughly three-hour evening starts at 6 pm at 5901 W Lawrence Ave. Dinner and parking are included; alcoholic drinks are not.

“Be ready for a lot of interactions and laughs. There was never a dull moment from the time we walked in, til we walked out.”

Check availability →Read our full review

5.Cocktail Adventure Tour 21+

★★★★★★★★★★5.0 · 9 reviews · 1 hour 30 minutes (approx.) · from $70

Start at Champagne on Main at 6 pm for a 90-minute, three-stop walk through Galena’s cocktail scene. You’ll have three full-size drinks, six tastings, and included snacks, finishing at The Grape Escape with bruschetta and a Chocolate Martini. Groups are limited to 10; alcohol-free and vegetarian requests must be made ahead.

“My partner and I ended up with a private tour which made the experience more personal and enjoyable. Our guide was knowledgeable and due to the size of our tour, chatted with us extensively which you don't always get to experience in larger groups.”

Check availability →Read our full review

6.3-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, some preserved in their original condition. Enter by secret passages, hear stories of bootlegging and racketeering, and get cocktail recommendations inspired by the era. Alan and Kai have led the tour, though your guide may differ. Luxury transport and city-limit hotel pickup are included; drinks cost extra.

“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.”

Check availability →Read our full review

7.Private Speakeasy Pub Crawl in Chicago with Local Historian

★★★★★★★★★★4.5 · 5 reviews · from $101

Spend about three hours visiting several Chicago-area bars that operated during Prohibition, entering through discreet doors and hearing stories of bootlegging, racketeering, and Al Capone. A private historian guide leads the route, with hotel or port pickup and private transport included. Drinks are extra. Past guides have included Conor, Stefan, and Kai, but your guide may differ.

“We had an amazing time and learned so much. Definitely a night to remember! The Untitled was my favorite place that we went to.”

Check availability →Read our full review