Chicago’s drinking tours blend history, craft beer, and local culture into efficient urban adventures. The standout Barrel Bus Tour offers climate-controlled comfort while visiting multiple breweries, making it ideal in any weather. We especially like the Prohibition Tour for its authentic speakeasy visits and fascinating historical commentary.
Most tours include generous tastings – typically 4-5 samples per stop – and knowledgeable guides who share insider tips about Chicago’s brewing scene. Walking tours through historic neighborhoods provide excellent value, combining sightseeing with craft beer education.
Our favorite options balance drinking time with cultural insights, avoiding tourist traps in favor of authentic local spots. Prices range from $45-85 per person, with most tours lasting 3-4 hours.
Let’s explore Chicago’s best drinking tours.
Key Points
- The Chicago Craft Brewery Barrel Bus Tour offers a unique climate-controlled, Prohibition-era-styled bus experience with up to 55 ounces of craft beer samples.
- The Milwaukee Harley-Davidson Museum & Brewery Day Tour provides a comprehensive experience by visiting the iconic Harley-Davidson Museum and historic Miller Brewery.
- The Sin and Suds Chicago Beer Tour features a 3-hour exploration of iconic Loop and South Loop neighborhoods, with beer tastings and pizza pairings.
- The Oktoberfest Malt Row Walking Brewery Tour offers a guided visit to three breweries in the Northcenter neighborhood, with craft beer tastings and exclusive discounts.
- The Private Speakeasy Pub Crawl presents a 1920s-themed tour exploring prohibition-era speakeasies, with skip-the-line access and luxury transportation.
Chicago Craft Brewery Barrel Bus Tour
This lively Chicago Craft Brewery Barrel Bus Tour takes guests on a guided exploration of the city’s thriving brewpub scene.
With over 270 positive reviews and a 97% recommendation rate, the tour showcases unique breweries and a brewing production facility, allowing travelers to learn the science behind beer-making.
Aboard a climate-controlled, Prohibition-era-styled barrel bus, guests can enjoy up to 55 ounces of craft beer samples while hearing entertaining stories about Chicago’s history.
The tour includes round-trip transportation, a professional guide, and gratuities, making it an all-inclusive experience.
Priced from $99.60 per person, the tour offers flexible booking and cancellation options, catering to various travel needs.
Read our full review: Chicago Craft Brewery Barrel Bus Tour Review
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Chicago: Milwaukee Harley-Davidson Museum & Brewery Day Tour
Explore Milwaukee’s rich industrial heritage and thriving beer culture with the Chicago: Milwaukee Harley-Davidson Museum & Brewery Day Tour. Priced at $125 per person, this 1-day excursion takes visitors to the iconic Harley-Davidson Museum, the bustling Milwaukee Public Market, and the historic Miller Brewery.
Along the way, you’ll enjoy 1.5 hours at each stop, giving you ample time to learn about the city’s vibrant past and present. With an expert guide, round-trip transportation, and optional admission fees, this tour offers a seamless and informative experience.
Reviewers praise the knowledgeable guide and the overall positive experience, making this an excellent choice for those seeking to discover Milwaukee’s highlights.
Read our full review: Chicago: Milwaukee Harley-Davidson Museum & Brewery Day Tour Review
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Sin and Suds Chicago Beer Tour
Immersing oneself in Chicago’s vibrant beer culture and criminal past, the Sin and Suds Chicago Beer Tour offers a captivating 3-hour exploration of the city’s iconic Loop and South Loop neighborhoods.
With a 100% traveler recommendation rate and a Badge of Excellence, this tour showcases popular downtown establishments like Exchequer Pub, Berghoff, and Vice District Brewing.
Guests can savor beer tastings and a pizza pairing while learning about the influence of beer styles on criminal enterprises, especially during Prohibition.
Meeting at the Exchequer Restaurant & Pub and ending at First Draft, the tour is conveniently accessible via CTA trains and accommodates various dietary needs and accessibility requirements.
Read our full review: Sin and Suds Chicago Beer Tour Review
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Chicago: Oktoberfest Malt Row Walking Brewery Tour
Traversing the heart of Chicago’s thriving craft beer scene, the Chicago: Oktoberfest Malt Row Walking Brewery Tour invites visitors to embark on a 3-hour exploration of three renowned breweries nestled within the Northcenter neighborhood.
Priced at $25 per person, the tour accommodates up to 10 participants and features guided visits to Begyle Brewing, Dovetail Brewery, and Cultivate by Forbidden Root.
Attendees can savor a variety of craft beers, learn about Chicago’s brewing history, and enjoy exclusive discounts and recommendations from the knowledgeable guide.
With wheelchair accessibility and the option to cancel up to 24 hours in advance, this tour provides a well-rounded Oktoberfest experience for beer enthusiasts visiting the Windy City.
Read our full review: Chicago: Oktoberfest Malt Row Walking Brewery Tour Review
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Private Speakeasy Pub Crawl in Chicago With Local Historian
Step back in time and experience the Roaring Twenties on the Private Speakeasy Pub Crawl in Chicago with a local historian.
This 1920s-themed tour explores prohibition-era speakeasies frequented by gangsters like Al Capone. Led by a costumed local expert, the experience includes luxury transportation, bottled water, and the option to purchase alcoholic drinks.
Guests will skip long lines and enjoy a guaranteed memorable journey through Chicago’s historic venues.
While reviews praise the knowledgeable guides and unique venues, some note the high price point compared to the cost of drinks.
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Chicago: Wine & Cheese or Beer & BBQ Thursday Evening Cruise
This Thursday evening cruise along Lake Michigan offers guests a choice between a Wine & Cheese or Beer & BBQ experience.
The Wine & Cheese option features a selection of fine wines and artisanal cheeses, while the Beer & BBQ option provides a sampling of local craft beers and delicious barbecue fare.
Both cruises provide stunning views of the Chicago skyline and a relaxing atmosphere to enjoy with friends or loved ones.
With a duration of 1.5 hours and prices ranging from $76.54, this cruise is a popular dining experience for both locals and visitors alike, boasting a 4.3 out of 5-star rating from 225 reviews.
Read our full review: Chicago: Wine & Cheese or Beer & BBQ Thursday Evening Cruise Review
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Walking Tour to Chicago Dive Bars
Exploring the gritty charm of Chicago’s legendary dive bars, this walking tour invites guests to enjoy the city’s vibrant underground drinking culture.
Led by local host Andy, the 2-hour experience takes visitors to a selection of the city’s most authentic watering holes. Participants receive a complimentary “Dive Right In” guidebook to learn the unwritten rules of these establishments.
The tour accommodates up to 12 travelers and is wheelchair accessible, though not recommended for those with certain medical conditions. Priced at $41.03 per person, the tour offers a flexible cancellation policy and convenient access via public transportation.
With an impressive 5-star rating, this walking tour promises an unforgettable glimpse into Chicago’s dive bar scene.
Read our full review: Walking Tour to Chicago Dive Bars Review
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Chicago: Craft Brewery Tour by Barrel Bus
A barrel-shaped bus offers visitors a unique way to explore Chicago’s thriving craft brewery scene on this 4-hour guided tour.
For $99.60, participants can visit three distinct breweries and sample approximately 45-55 ounces of craft beer. The tour includes a VIP behind-the-scenes experience at a top nano-brewery and interactive party games.
Transportation, a professional guide, and hotel pickup/drop-off are provided. While not suitable for those under 21 or with mobility issues, the tour has received overwhelmingly positive feedback, with an impressive 4.9/5 rating from 40 reviews.
Travelers praise the tour’s engaging and enjoyable nature, making it a must-try for anyone seeking a memorable craft brewery experience in Chicago.
Read our full review: Chicago: Craft Brewery Tour by Barrel Bus Review
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Chicago Local Brewery Expedition With Homemade Guacamole
Embarking on a captivating Chicago Local Brewery Expedition, visitors enjoy the vibrant craft beer scene of the city.
This 4-brewery tour offers 15 ounces of craft beer and 3-5 ounce glasses of handcrafted brews, complemented by homemade guacamole and corn tortillas.
Led by knowledgeable guides, the experience accommodates up to 20 travelers and begins at 1725 W Hubbard St, concluding at 417 N Ashland Ave.
While not wheelchair accessible, the tour is stroller-friendly and located near public transportation.
Though not recommended for pregnant travelers, most participants can enjoy this 5-star rated adventure, which features a flexible cancellation policy and pay-later option.
Read our full review: Chicago Local Brewery Expedition With Homemade Guacamole Review
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Fun Chicago Bike Tour With Pizza, Hot Dogs, Cupcakes and Beer
Cycling through Chicago’s vibrant neighborhoods, this fun-filled bike tour offers a delightful culinary journey featuring pizza, hot dogs, cupcakes, and beer.
Priced from $179 per person, the tour provides a morning or evening start time and two unique itineraries, with a maximum group size of 15 travelers.
Included are a bicycle, helmet, water bottle, friendly local guide, and samples at various eateries and breweries.
With moderate fitness required, the tour operates rain or shine, and special dietary needs can be accommodated.
Ideal for both first-time visitors and locals seeking an engaging way to experience Chicago’s iconic foods and drinks.
Read our full review: Fun Chicago Bike Tour With Pizza, Hot Dogs, Cupcakes and Beer Review
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Recap
Chicago offers a variety of unique drinking tours to satisfy any beer enthusiast. From craft brewery tours and speakeasy crawls to Oktoberfest celebrations and dive bar explorations, there’s something for all. Whether you prefer to explore by bus, bike, or on foot, these tours provide an excellent way to discover Chicago’s vibrant drinking scene and learn about the city’s rich history.