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“Great way to try a variety of Chicago craft beers. Unique mode of transportation. Great way to see different parts of Chicago.”
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.
“Ted did a great job and provided a lot of information!”
Oktoberfest-style beer walk in Chicago’s Malt Row. Small group visits Dovetail, Begyle and Cultivate with tastings and history.
“Adam was a great tour guide and super knowledgeable and passionate about the Chicago beer scene. Had a really great experience and learned a lot. Would recommend for anyone looking for a day out and exploring some new places in the area.”
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.
“Adam was so knowledgeable and made the experience so fun!!! 10 out of 10 - would recommend!! This was such a good find. You learn about beer and Chicago's history!”
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 Milwaukee Art Museum was a visual masterpiece—its stunning architecture and lakefront setting made for the perfect introduction to the city’s creative spirit. Inside, the collection was diverse and thoughtfully curated, with something to capture every kind of art lover. The Milwaukee Public Market was a lively and delicious stop. From artisan cheeses to fresh-baked…”
Private 1920s Chicago speakeasy pub crawl with a local historian, secret entrances, hotel pickup, and optional Prohibition-era cocktails.
“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…”
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.
