Chicago’s best drinking tours showcase the city’s rich brewing heritage and modern craft scene. The standout Craft Brewery Barrel Bus Tour offers generous tastings while traveling between locations in comfort. Budget-conscious travelers will appreciate the wallet-friendly Oktoberfest Walking Tour through Logan Square. History buffs can explore Chicago’s gangster past on the Sin and Suds Beer Tour, which pairs local brews with prohibition-era stories.
We especially love the Haunted Pub Crawl for its spine-tingling tales and historic taverns, and the Local Brewery Expedition wins points for including fresh guacamole with its excellent beer selections. The Craft Brewery Tour by Barrel Bus excels with its premium service and behind-the-scenes access.
Let’s explore these essential Chicago drinking tours in detail.
Key Points
- The Chicago Craft Brewery Barrel Bus Tour offers an immersive craft beer experience with extensive sampling, knowledgeable guides, and a unique transportation style.
- The Sin and Suds Chicago Beer Tour combines the city’s organized crime history with craft beer tastings and pizza pairings for an educational and entertaining experience.
- The Chicago Haunted Pub Crawl provides a thrilling blend of history, ghost stories, and visits to infamous haunted watering holes, catering to history buffs and thrill-seekers.
- The Chicago: Malt Row Walking Brewery Tour offers a wheelchair-accessible, guided exploration of the Ravenswood neighborhood’s renowned breweries with exclusive discounts.
- The Chicago: Wine & Cheese or Beer & BBQ Cruise offers a memorable experience with scenic views along the Chicago River, combining beverages with complementary food pairings.
Chicago Craft Brewery Barrel Bus Tour
The Chicago Craft Brewery Barrel Bus Tour offers visitors a guided exploration of the city’s thriving brewpub scene.
With a 97% traveler recommendation based on 274 reviews, the tour includes visits to unique breweries and a brewing production facility, where guests receive 45-55 ounces of craft beer samples.
Transported by a Prohibition-era-styled barrel bus, the tour features a knowledgeable guide who provides live commentary and an in-depth look at the brewing process.
Guests praise the friendly guide, Ted, and the social interaction with fellow travelers, though some suggest including food options.
The tour, which costs from $99.60 per person, isn’t wheelchair accessible but is near public transportation.
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Chicago: Oktoberfest Walking Brewery Tour in Logan Square
This 3-hour Chicago: Oktoberfest Walking Brewery Tour in Logan Square offers visitors a unique exploration of the neighborhood’s thriving craft beer scene.
Starting at Palmer Square Park, the tour visits three local breweries – Solemn Oath, Revolution, and Hopewell – where guests enjoy exclusive discounts and learn about the history of Chicago’s brewing industry.
Along the way, the knowledgeable guide provides insightful commentary and recommendations. The tour is wheelchair accessible, and guests can easily reach the starting point via public transportation.
While alcohol isn’t provided, guests can purchase their own drinks at each stop. Priced at $25 per person, this tour is a great way to discover Logan Square’s vibrant craft beer culture.
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Sin and Suds Chicago Beer Tour
Combining Chicago’s rich history of organized crime and its burgeoning craft beer scene, the Sin and Suds Chicago Beer Tour offers an immersive look into the city’s illicit past.
Over three hours, guests explore the Loop and South Loop neighborhoods, visiting popular establishments and sampling local brews. Along the way, they learn about Chicago’s criminal history, including the role of beer during Prohibition.
The tour includes beer tastings, a pizza pairing, and insights from a knowledgeable guide. With 100% positive reviews, the Sin and Suds tour provides an entertaining and educational experience for both locals and visitors alike.
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Chicago Haunted Pub Crawl: Water Tower Specter and Beyond
A popular haunted tour in Chicago, the Chicago Haunted Pub Crawl takes visitors on a spooky exploration of the city’s most infamous watering holes and ghostly hotspots.
Over 2 to 3 hours, the tour visits locations like the legendary Water Tower, said to be haunted by the spirit of a young woman who perished in a fire.
Guests will also learn about the city’s notorious Prohibition-era past and the sinister figures who once prowled its shadowy streets.
With a 4.7 rating from over 1,280 reviews, this guided walking tour offers a thrilling and unique way to experience Chicago’s dark history.
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Chicago Local Brewery Expedition With Homemade Guacamole
Explore the vibrant local brewery scene of Chicago on this guided expedition, complete with homemade guacamole and freshly baked corn tortillas.
Sip your way through 15 ounces of craft beer across 3-5 different handcrafted varieties. Led by a knowledgeable guide, you’ll visit the meeting point at 1725 W Hubbard St and end at 417 N Ashland Ave.
While not wheelchair accessible, the tour is stroller-friendly and near public transportation. Most travelers can participate, though it’s not recommended for pregnant individuals.
With a 5.0 rating based on 1 review, this local brewery expedition offers a delicious and memorable way to experience Chicago’s vibrant drinking culture.
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Chicago: Milwaukee Harley-Davidson Museum & Brewery Day Tour
On this day-long excursion, travelers journey from Chicago to Milwaukee to enjoy the rich heritage and vibrant culture of the Harley-Davidson brand.
The tour includes admission to the Harley-Davidson Museum, where guests can explore motorcycle history from 1903 to the present.
Next, visitors explore the Milwaukee Public Market, sampling Wisconsin’s renowned specialty foods like cheese and sausage.
The tour then takes guests to the iconic Miller Brewery, where they learn about brewing history and enjoy beer samples.
Along the way, participants catch a glimpse of the Milwaukee Art Museum, one of the largest art museums in the U.S.
This comprehensive tour offers an enriching and enjoyable experience for Harley enthusiasts and beer lovers alike.
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Fun Chicago Bike Tour With Pizza, Hot Dogs, Cupcakes and Beer
This fun Chicago bike tour takes participants on a delectable journey through the city’s vibrant food and beverage scene.
Operating rain or shine, the tour offers morning and evening start times with two unique itineraries, catering to a maximum of 15 travelers.
Highlights include pizza, hot dogs, cupcakes, and beer samples at various local spots.
Riders will enjoy a bicycle, helmet, and water bottle, as well as the expertise of a friendly local guide.
With inclusions such as all fees, taxes, and gratuities, this tour provides an exceptional value.
Dietary restrictions can be accommodated, though gluten-free and vegan options are limited.
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Chicago: Craft Brewery Tour by Barrel Bus
Amid the bustling city of Chicago, craft beer enthusiasts can embark on an unforgettable journey aboard a unique barrel-shaped bus for the “Chicago: Craft Brewery Tour by Barrel Bus.”
This 4-hour experience immerses participants in the heart of the Windy City’s thriving craft beer scene, offering them the opportunity to visit three distinct breweries and sample approximately 45-55 ounces of craft beer.
The tour includes a VIP behind-the-scenes tour at a top nano-brewery, interactive party games, and live commentary from a knowledgeable guide.
With a 4.9/5 rating based on 40 reviews, this tour promises an exceptional craft beer experience in Chicago.
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Walking Tour to Chicago Dive Bars
Dive into Chicago’s vibrant underground bar scene on this captivating walking tour.
Led by local guide Andy, this 2-hour experience takes you to the city’s iconic dive bars, where you’ll uncover the unwritten rules of these laidback watering holes.
Kicking off outside the Chipp Inn, you’ll visit a maximum of 12 travelers, receiving the “Dive Right In” book to help navigate these hidden gems.
Wheelchair accessible and near public transit, the tour caters to most, though it’s not recommended for those with back issues or serious medical conditions.
At just $41.03 per person, this 5-star rated experience promises an authentic taste of Chicago’s gritty bar culture.
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Chicago: Malt Row Walking Brewery Tour
Chicago’s Malt Row Walking Brewery Tour provides an unparalleled opportunity to explore the city’s vibrant craft beer scene.
This 3-hour, guided walking tour takes you through the Ravenswood neighborhood, visiting three renowned breweries: Begyle Brewing, Dovetail Brewery, and Cultivate by Forbidden Root.
You’ll sip on a variety of craft beers, learn about Chicago’s brewing history, and enjoy exclusive discounts and reserved seating at each stop.
With a maximum group size of 10, you’ll receive personalized recommendations from the knowledgeable guide.
The tour is wheelchair-accessible, and you can cancel up to 24 hours in advance for a full refund.
Bring comfortable shoes, cash, and a thirst for craft beer exploration.
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Chicago: Wine & Cheese or Beer & BBQ Thursday Evening Cruise
On Thursday evenings, visitors can embark on a memorable cruise along the Chicago River, choosing between two distinct experiences – the Wine & Cheese Cruise or the Beer & BBQ Cruise.
The Wine & Cheese Cruise offers a 2-3 hour journey, allowing guests to savor a selection of fine wines and artisanal cheeses while taking in the city’s stunning architecture.
Alternatively, the Beer & BBQ Cruise provides a delightful pairing of local craft beers and delicious barbecue dishes.
Both options are priced at $76.54 and boast a 4.3 rating from over 225 reviews, making them a popular choice for those seeking a unique and enjoyable evening on the water.
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Sum Up
Chicago’s drinking tours offer something for every taste, from craft brewery excursions to haunted pub crawls. Whether you’re a beer enthusiast, a wine lover, or just looking for a unique experience, there’s a tour that will suit your interests. Explore the city’s vibrant drinking culture and discover the best spots, guided by knowledgeable local experts.