CHICAGO · BAR CRAWLS
The nights worth heading out for.
The 5 chicago bar crawls worth heading out for. The nights groups still talk about the next morning, with prices, run times and who runs the crawl.
Sunset Chicago River architecture cruise with included cocktail, award-winning docents, 50+ buildings, and 100-year-old bascule bridges.
Most Popular“A great tour our guide was very informative. A great way to learn and see more about Chicago”
Ride a Chicago River cocktail cruise for 90 minutes of skyline architecture, included drinks, and live narration near Wrigley and Michigan Ave.
“This cruise was not a cocktail cruise, it was a snooze fest. I was not accepting to learn about the architecture of Chicago. I would not recommend this cruise for anyone. This was false advertisement.”
Step into a 1929 speakeasy for dinner, homemade-style hooch, and a 90-minute twenties musical comedy show in Chicago.
“Absolutely brilliant evening! Vito and the team put on a fantastic night.”
Private 3-hour Chicago speakeasy VIP tour with secret entrances, Prohibition stories, and luxury chauffeur transport to 3–4 working bars.
A private 1920s Prohibition-style pub crawl in Chicago with a local historian, secret entrances, and period cocktails you’ll budget for separately.
“We had an amazing time and learned so much. Definitely a night to remember! The Untitled was my favorite place that we went to.”
Bar crawls, cocktail tours and after-dark walks, in every city we cover.
