CHICAGO · ILLINOIS
The best of Chicago.
The 9 best drinking tours in Chicago, with honest prices, run times and who you book through. Which ones are worth your time downtown, and what each one actually gets you.
Ride Chicago’s Prohibition-style barrel bus for a 3-brewery craft beer tour with big tastings, great guides, and no driving stress.
Most Popular“Fun bus, fun talking to all of your fellow travelers. Each stop was a different experience but you feel welcomed and wanted at each place. They knew we were coming and were ready for the group to walk in. Very fun afternoon.”
A barrel-shaped bus takes you to three Chicago breweries for VIP production tours, games, and 45–55 oz of craft beer in 4 hours.
“Had a great time! It was fun and informative (but not in a boring way) and great to be able to check out a few breweries we may not have been to otherwise.”
Oktoberfest-style beer walk in Chicago’s Malt Row. Small group visits Dovetail, Begyle and Cultivate with tastings and history.
“Loved our walking brewery tour with Adam! He was incredibly knowledgeable about the history of brewing in Chicago and told us the entire history.”
75-minute tiki bar cruise from Dock 12 with tropical drinks (sold onboard), a climate-controlled lounge, and Chicago River or Lake Michigan views.
“Crowded with long lines for drinks.”
A 3-hour Logan Square walking tour linking three breweries, with beer discounts and Chicago brewing history. Mobile ticket, small group.
“Such a fun time! Very informative tour and so many fun stops. Each brewery had a special discount for our group. We learned so many interesting chicago history facts.”
Small-group 3.5-hour Chicago pub walk through the Loop and River North with architecture stops, classic taverns, and 21+ stories. Drinks extra.
“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.”
Chicago to Milwaukee day trip with guided transport, optional Harley-Davidson and Miller brewery tours, plus Milwaukee highlights.
“The Harley-Davidson Museum was a must-see—packed with over 450 motorcycles and rich with fascinating stories that even non-riders would appreciate. The Milwaukee Public Market was a food lover’s paradise, full of unique local vendors and vibrant energy. The Miller Brewery tour was another standout: learning about the brewing process while enjoying authentic beer samples made…”
Private 1920s Chicago speakeasy pub crawl with a local historian, secret entrances, hotel pickup, and optional Prohibition-era cocktails.
“We had an amazing time and learned so much. Definitely a night to remember! The Untitled was my favorite place that we went to.”
90-minute Chicago West Loop brewery tour with homemade guacamole, corn tortillas, and guided craft beer tastings at Goose Island and District Yards.
“Ronaldo was great! Communicated all the details and followed up. Another awesome experience with Viatour”
From the river and the skyline to the gangster trails, the lakefront and the deep-dish counters, every way to spend a day in the city.
