The 10 Best Drinking Tours in Chicago

1.Chicago Craft Brewery Barrel Bus Tour

★★★★★★★★★★5.0 · 339 reviews · 3 hours 45 minutes (approx.) · from $99Our pick

Meet your guide at 600 N Clark Street in River North, then board a custom barrel-shaped bus for a roughly four-hour visit to up to three Chicago breweries. Tastings add up to 45 to 55 ounces, with Chicago and Prohibition stories along the route. Stops vary, and a production-facility visit requires closed-toe shoes.

“So much fun, David was a great host and so much fun, we had a great time and would definitely recommend!”

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2.Craft Brewery Tour by Barrel Bus

★★★★★★★★★★5.0 · 56 reviews · 4 hours · from $99

Spend four hours visiting three Chicago breweries aboard a custom barrel-shaped bus. Your English-speaking guide handles the driving and adds live commentary, while you sample 45 to 55 ounces of craft beer and get a VIP look inside a nano-brewery. Bring ID and closed-toe shoes; food is not included.

“Loved this tour! Great guides, atmosphere and breweries. Would do it again :)”

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3.Oktoberfest Walking Brewery Tour in Malt Row

★★★★★★★★★★5.0 · 28 reviews · from $39

Start at Northcenter Town Square at 2 pm and walk with a small group to Dovetail, Begyle, and Cultivate by Forbidden Root. Your guide connects Chicago’s brewing past with today’s local beer scene, while you get time at each brewery to order a drink or two. The tour costs $39; drinks are generally extra.

“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.”

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4.Tiki Bar Cruise on Chicago River or Lake Michigan

★★★★★★★★★★3.8 · 16 reviews · 1h 15m · from $41

Settle into a tiki-themed boat with palm trees and thatch roofing for a 75-minute Chicago cruise. The route covers the river’s North, South, and main branches, with skyline views, music, a climate-controlled lounge, restrooms, and drinks for purchase. The boat starts and ends at Dock 12. An English-speaking host or greeter is listed, but guided commentary is not specified.

“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.”

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5.Chicago to Milwaukee Day Trip: City Tour with Miller Brewery

★★★★★★★★★★4.2 · 16 reviews · 1 day · from $125

Ride from Chicago to Milwaukee with an English-speaking guide, then spend the day among motorcycle history, market stalls, beer-making heritage, and Lake Michigan scenery. You get 90 minutes at the Public Market and a 30-minute lakefront stop. The Harley-Davidson Museum and Miller Brewery tour are optional, so check your booking choice and admission costs before you go.

“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...”

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6.Oktoberfest Walking Brewery Tour in Logan Square

★★★★★★★★★★5.0 · 10 reviews · from $25Best value

In Logan Square, walk with a guide from Palmer Square Park to Solemn Oath, Revolution Brewing, and Hopewell Brewing. Expect Chicago beer history, time to explore each brewery, and discounts on selected flights. Guides Adam and Brent have led tours, though your guide may vary. Drinks cost extra; the 2 pm tour lasts about three hours.

“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.”

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7.Walking Tour: Historic Chicago Pubs in River North and the Loop

★★★★★★★★★★5.0 · 9 reviews · from $65

Start at the Marquette Building at 4:00 pm, then walk through the Loop and River North to four historic pubs. A local guide connects Chicago architecture, media lore, and tavern history, with stops at The Berghoff, Brehon Pub, Green Door Tavern, and Monk’s Pub. The group is capped at 10; drinks and food cost 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.”

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8.Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights

★★★★★★★★★★5.0 · 8 reviews · 8 to 10 hours (approx.) · from $125

Leave Chicago at 8:00 am for an 8 to 10 hour Milwaukee outing in a comfortable vehicle with a guide-driver. Explore the Public Market, see the Art Museum’s striking exterior, and choose whether to add the Harley-Davidson Museum and Miller Brewery tour. The group is capped at 14.

“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...”

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9.Private Speakeasy Pub Crawl in Chicago with Local Historian

★★★★★★★★★★4.5 · 5 reviews · from $101

Spend about three hours visiting several Chicago-area bars that operated during Prohibition, entering through discreet doors and hearing stories of bootlegging, racketeering, and Al Capone. A private historian guide leads the route, with hotel or port pickup and private transport included. Drinks are extra. Past guides have included Conor, Stefan, and Kai, but your guide may differ.

“We had an amazing time and learned so much. Definitely a night to remember! The Untitled was my favorite place that we went to.”

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10.Chicago Local Brewery Expedition with Homemade Guacamole

★★★★★★★★★★5.0 · 4 reviews · 1 hour 30 minutes (approx.) · from $63

Meet at Goose Island Beer Co. for three 5-ounce craft beer tastings, homemade guacamole, and corn tortillas made by Chef Carla. Then walk with your guide to District Yards Brewing and a nearby group of four breweries. The 90-minute tour costs $63 per person, runs in English, and has a maximum group size of 20.

“Ronaldo was great! Communicated all the details and followed up. Another awesome experience with Viatour”

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