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.
“This was a fabulous tour! David, our tour guide, was knowledgeable and friendly. A good variety of beers were sampled. Highly recommend this tour!”
Oktoberfest-style beer walk in Chicago’s Malt Row. Small group visits Dovetail, Begyle and Cultivate with tastings and history.
“Great beers with a super knowledgeable guide. Learned all about the Chicago brew scene, past and present. Great advice and recommendations on all our stops.”
75-minute tiki bar cruise from Dock 12 with tropical drinks (sold onboard), a climate-controlled lounge, and Chicago River or Lake Michigan views.
“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.”
A 3-hour Logan Square walking tour linking three breweries, with beer discounts and Chicago brewing history. Mobile ticket, small group.
“It was both educational and fun. For someone who’s done several brewery tours, this one is unlike any I’ve done, giving you an intimate look into Chicago’s brewery scene.”
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.
“At $330/person I was surprised that the operator/guide did not provide the drinks at the bars. He was very knowledgeable about the city and we had a great time. It was just too expensive.”
90-minute Chicago West Loop brewery tour with homemade guacamole, corn tortillas, and guided craft beer tastings at Goose Island and District Yards.
“Great chips and guacamole. He sure knew a lot about beer. Also had good hints about what to see in Chicago”
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.
