Chicago · DRINKING TOURS
This is the shortlist to send a friend: 13 drinking tours worth the money, each with its price, its traveller verdict and the one thing to know before you commit.
Ride a Prohibition-inspired barrel bus through River North to up to 3 Chicago breweries, sampling 45 to 55 oz of craft beer.
“It was a very enjoyable tour. Ted the tour guide was very knowledgable about the history behind beer in Chicago and all the Breweries were unique.”
Ride a barrel bus through Chicago breweries for 3 stops, VIP nano-brewery production tour, and 45 to 55 ounces of beer in 4 hours.
“What a tour! Very knowledgeable and friendly guide. Thoroughly enjoyed every stop, and the barrel bus is great fun to be on. Fantastic selection of beers tasted at great venues. The your of Revolution Brewery is a real highlight. Highly recommended”
A $39 small-group Oktoberfest-style walking brewery tour through Chicago’s Malt Row, with guided history and tastings at Dovetail, Begyle, and Cultivate.
“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 on Chicago River, starts at Dock 12, with tropical cocktails available and skyline 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.”
Milwaukee in one day from Chicago with Harley-Davidson Museum, free time at Milwaukee Public Market, optional Miller tastings, and lakefront sights.
“This Milwaukee day trip from Chicago was such a refreshing and well-organized escape! The itinerary perfectly balanced culture, history, and local flavor. From diving into motorcycle heritage at the Harley-Davidson Museum to sampling brews at the Miller Brewery, each stop added something special. The Milwaukee Public Market was a foodie’s dream, and even the brief stop at the Milwaukee Art Museum offered beautiful lakefront views and striking architecture. I also want to take a moment to highlight out guide—professional, engaging, and incredibly knowledgeable. He kept the tour running smoothly, shared great insights throughout the day, and made sure everyone felt looked after. Whether you’re...”
Oktoberfest-style walking brewery tour in Logan Square: three breweries, guided Chicago beer history, and discounted flights for $25.
“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.”
Historic Loop and River North pub walk with a local guide, five stops, architecture landmarks, and included transit. Drinks are extra.
“Had a great time! Took my relatives from out of town who are very picky about activities and they loved this tour a lot. Tom is a great local guide who knows his city very well and brought lots of neat materials and photos to bring the someRead more”
Chicago to Milwaukee day trip with optional Harley and Miller tours, Public Market food stops, and lakefront Art Museum views for $125.
“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 for a fun and memorable stop. To top it off, the Milwaukee Art Museum left us in awe. Its striking architecture and lakefront setting, along with its impressive collection, provided the perfect finale to a well-rounded day. This tour was incredibly well-organized and full of variety, making it ideal for travelers of al...”
Private 3-hour Chicago speakeasy crawl with a local historian, hotel pickup, secret entrances, and Prohibition-era cocktail stops. Drinks extra.
“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.”
1.5-hour West Loop brewery crawl with homemade guacamole and tortillas, plus beer flights at Goose Island and District Yards. Small group.
“Very knowledgeable about beers and the local area! Want to get to know the West Loop? This is a great start!”
Walk Chicago’s West Loop drinking culture on a 2.5-hour small-group tour with five classic bars, local stories, and on-your-own drinks.
“Awesome tour!!! If you want to feel like a local this is the tour for you!! Vince was a great guide. Full of great tips”
Explore three mid-century cocktail bars in Ukrainian Village with water included, one cover charge included, and live music at the final stop.
“This is a great way to experience a less touristy Chicago neighborhood. Real bars with history and hanging out with the locals! We went to 3 bars in two neighborhoods - lots of different drinks is to try and options to dance if you want to stay later. Ronaldo is a great guide and fun to hang out with as well!”
A 4-hour Chicago bike tour with deep-dish pizza, hot dogs, brownies, craft beer, and lakefront views. Guided, slow pace, great value.
“My husband and I thoroughly enjoyed the tour of Chicago by bike. It is such a fun way to see the city. I highly recommend going on this tour, even if you haven't ridden a bike in a long time. The pace is slow so that you can take in all the sights and there are plenty of stops along the way to eat yummy food and have a drink. It definitely didn't feel like 13 miles to me. Dan was an incredible host, sharing great stories and facts about the city of Chicago. He led us confidently through the streets of Chicago like the pro that he is. I…”
Every kind of day out in the city, and the best of each.
