Chicago · DRINKING TOURS
10 tours
Chicago runs more of these than anyone can sort through in a week off. The 10 below are the ones to book, with what each costs, how long it takes and the sort of trip it suits.
A Prohibition-inspired barrel bus tour that lines up visits to up to three Chicago craft breweries, with 45 to 55 ounces of beer samples.
“So much fun, David was a great host and so much fun, we had a great time and would definitely recommend!”
Ride a barrel-shaped bus through Chicago’s craft beer scene, tasting at three breweries with one VIP nano-brewery production tour, games, and guide-led fun.
“Ted did a great job and provided a lot of information!”
A small-group walking beer tour through Chicago’s Malt Row, visiting Dovetail, Begyle, and Cultivate with tastings and discounts.
“Loved our walking brewery tour with Adam! He was incredibly knowledgeable about the history of brewing in Chicago and told us the entire history.”
Tiki bar cruise on Chicago River or Lake Michigan, 75 minutes of skyline views, tropical vibes, and full bar drinks for purchase.
“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.”
Chicago to Milwaukee day trip with Harley-Davidson Museum, Historic Third Ward Public Market, optional Miller Brewery tastings, and Lakefront views.
“Personal service was great Nico our guide and driver was excellent and very helpful. No need to change anything”
Oktoberfest Walking Brewery Tour in Logan Square: visit 3 breweries, get beer flight discounts, and learn Chicago brewing stories on a 3-hour walk.
“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.”
A small-group 21+ walking tour through Chicago’s Loop and River North, hitting classic pubs, architecture stops, and media speakeasy lore.
“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 lakefront sights and optional Harley-Davidson and Miller Brewery tours, plus Public Market stops.
“Just before we were heading back to Chicago The operator will tell you that you owe him a $12 per person service fee after paying $125.00 per person. We told him we were paid in full. He insisted but we didn’t give him any more money. At first he didn’t start driving but after about 10 minutes he started driving us back to Chicago. Smh”
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.”
Taste West Loop craft beer at Goose Island and District Yards with homemade guacamole and tortillas, plus guided beer flights.
“Ronaldo was great! Communicated all the details and followed up. Another awesome experience with Viatour”
