Chicago · CHICAGO COCKTAIL & SPEAKEASY TOURS
6 tours
Chicago runs more of these than anyone can sort through in a week off. The 6 below are the ones to book, with what each costs, how long it takes and the sort of trip it suits.
Sip a cocktail while an award-winning guide explains Chicago River architecture, from historic towers to lit skyline at dusk.
“I had a great experience, the staff was friendly and the tour guide was very informative, I learned a lot of interesting facts about the buildings and had a good time sightseeing with a drink in my hand. 5 out of 5 stars”
Sip a drink while a live guide points out 50 Chicago skyscrapers on a 90-minute river cruise, with photos, snacks, and great views.
“There was one bartender it took forever to get our drink. I wasn’t expecting it to be the architecture tour because it states cocktail cruise. Kind of disappointed about that.”
Chicago's Vito's Vault is a 1929 speakeasy dinner theatre with a served meal and 90 minutes of songs and comedy.
“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.”
A 90-minute 21+ cocktail crawl in Galena with three full-size drinks, food pairings, and a small-group route ending at The Grape Escape.
“We had a wonderful time last night on the cocktail adventure tour! Devin was super knowledgeable about not only Galena history but the food and drink pairings that we tried. It was great to get right into 3 different locations and end the night with a great table for live music at the Grape Escape. We also tried some food we wouldn’t normally order and really enjoyed it.”
Private Chicago speakeasy VIP tour with a historian, secret entrances, luxury pickup, and 3-4 working 1920s bars for cocktails.
“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.”
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.”
