The 8 Best Drinking Tours in Chicago
Chicago’s reputation as a city of neighborhoods, culture, and architecture is well-earned. But beyond its skyline, it’s a city that loves its craft beers, historic pubs, and hidden speakeasies. With so many distinctive options, finding the right tour can be tricky. Whether you’re into tasting the latest microbrew or exploring Chicago’s boozy history, this guide covers the top drinking tours that promise a memorable and authentic experience.
These tours stand out for their variety—some focus on craft breweries with behind-the-scenes access, others on historic pub walks, and a few take you on day trips to Milwaukee for a full culture. Each offers its own flavor, so read on to find your perfect pour in the Windy City.
1. Chicago: Craft Brewery Tour by Barrel Bus
At number one, the Chicago: Craft Brewery Tour by Barrel Bus combines fun transportation with a focus on Chicago’s innovative craft beer scene. For four hours, you hop on a barrel-shaped bus that visits some of the city’s hippest nano-breweries. This tour is perfect for those wanting a relaxed, social experience while sampling delicious craft beers.
Unique to this tour is the VIP behind-the-scenes tour at a top nano-brewery, giving you insights into small-batch brewing that you won’t get on larger tours. The interactive party games and friendly guide make it more than just a beer tasting; it’s a lively social event. With a 4.9-star rating from 45 reviews, the tour is clearly a hit. Guests rave about the knowledgeable guide, the fun atmosphere, and the variety of beers tasted.
This experience is best suited for those who enjoy group activities, hands-on brewery visits, and fun, informal tasting. For $100, it offers a good value considering the VIP access and extensive brewery visits. Just check the availability because this popular tour sells out fast.
Bottom Line: Ideal for beer lovers seeking a lively, behind-the-scenes look at Chicago’s craft scene with a party vibe.
2. Oktoberfest Walking Brewery Tour in Malt Row
Ranking second, the Oktoberfest Walking Brewery Tour in Malt Row explores Chicago’s historic beer district in Ravenswood. This small-group tour takes you to three distinct breweries over about four hours, with plenty of time to enjoy samples at each stop. Priced at just $39, it’s a budget-friendly way to learn about Chicago’s brewing roots.
What makes this tour stand out is its focus on European-style beers, like Dovetail Brewery’s traditional Kolsch and Hefeweizen. The guide offers history and fun facts during the tasting sessions, enriching your understanding of Chicago’s brewing heritage. The tasting opportunities are generous—more than enough to sample the beers and chat with the staff. Reviewers mention that the guide is helpful and the reserved seating and discounts at each brewery enhance the experience.
This tour is great for history buffs and casual drinkers who want a relaxed, educational outing without breaking the bank. It’s perfect for those who want to walk and explore, especially since it’s conveniently located near transit options.
Bottom Line: A well-rounded, affordable introduction to Chicago’s Malt Row brewing scene, especially suited for those interested in European styles and history.
3. Oktoberfest Walking Brewery Tour in Logan Square
Ranking third, this Oktoberfest Walking Brewery Tour in Logan Square offers a more concentrated experience in one of Chicago’s most dynamic neighborhoods. At just $25 for about three hours, it’s an accessible option to explore three breweries, including Chicago’s largest independent.
The tour kicks off at Solemn Oath Brewery with discounted tastings, then moves on to Revolution Brewing, where you can enjoy discounted flights and a full menu, and finishes at Hopewell Brewing, known for its innovative beers. Visitors cite the informative guides and the opportunity to get to know each brewery intimately. The 5-star reviews show that it’s a favorite for those who want a mix of learning, tasting, and neighborhood exploring.
Ideal for locals and travelers looking for a neighborhood vibe, this tour provides a good balance of price and content. The focus on craft beers within a vibrant setting makes it a solid choice for a casual afternoon.
Bottom Line: Perfect for those wanting an affordable, neighborhood-based beer tour with a focus on local favorites.
4. Walking Tour: Historic Chicago Pubs in River North and the Loop
Number four, the Walking Tour: Historic Chicago Pubs in River North and the Loop, offers a deep dive into Chicago’s tavern culture. Over 3.5 hours, you’ll visit five iconic pubs, each with their own stories, from the oldest operating restaurant to media watering holes.
The tour is designed for those interested in local history and architecture as well as drinking. The tour includes stories about Chicago’s past and some of its most famous neighborhoods. You’ll end up in bars filled with antique decor and Chicago character. Reviewers mention the knowledgeable guides and the mix of architecture and pub stories, making it a comprehensive cultural experience.
Priced at $65, this tour is best suited for history and architecture enthusiasts who also want a good drink. The focus on local, historic pubs makes it a different experience from brewery-centric tours, and it’s ideal for people wanting an authentic taste of Chicago’s past.
Bottom Line: A rich, historic pub crawl perfect for those interested in Chicago’s architecture and drinking history.
5. NOT OPERATING: Walking Tour to Chicago Dive Bars
Number five, the Walking Tour to Chicago Dive Bars is currently not operating, but if it resumes, it promises a local-side of Chicago’s dive bar scene. Limited reviews praise its authenticity and the chance to explore five classic dives with a knowledgeable guide.
This 2.5-hour tour costs $45, focusing on the city’s legendary dive bars that have been part of Chicago’s fabric for decades. It’s best suited for adventurous drinkers wanting to experience the gritty, unpolished side of Chicago nightlife. Keep an eye out for future dates if this tour reopens.
Bottom Line: Though temporarily unavailable, it’s a great choice for lovers of authentic, unpretentious bars when it’s back.
6. Chicago Local Brewery Expedition with Homemade Guacamole
Number six, the Chicago Local Brewery Expedition with Homemade Guacamole offers a small group tour focusing on five local microbreweries in the Fulton Market district. For about 1.5 hours, you’ll visit two locations, starting with Goose Island, where homemade guacamole and tortillas complement three different craft beer tastings.
What makes this tour stand out is the culinary touch—your guide Carla will prepare homemade guacamole, adding a special flavor to the experience. The tour’s focus on handcrafted, local beers makes it appealing for those interested in artisanal brewing. Reviewers appreciate the informative guide and the variety of beers.
At $54 per person, it offers a hands-on, intimate experience for those who want to explore Chicago’s craft beer scene with a culinary twist. It’s best suited for beer aficionados who also enjoy good food.
Bottom Line: A fun, foodie-focused tour perfect for those who love craft beers and homemade snacks.
7. Private Speakeasy Pub Crawl in Chicago with Local Historian
Ranking seventh, the Private Speakeasy Pub Crawl in Chicago takes you back to the 1920s with a historian guide leading a private tour of secret entrances and hidden bars. For about three hours, you explore Chicago’s Prohibition-era spots—perfect for fans of history, architecture, and craft cocktails.
The highlight is discovering hidden speakeasies once frequented by gangsters like Al Capone, with the option to order Prohibition-style cocktails (not included). Reviewers praise the knowledgeable guide and the immersive experience, especially if you dress in period attire. The tour costs $101, including hotel pickup and drop-off, making it very convenient.
Ideal for history lovers and those seeking a unique night out, this private tour offers a blend of entertainment and education that makes it stand out. Due to its private nature and storytelling, it’s perfect for special occasions or groups.
Bottom Line: The best choice for history and cocktail enthusiasts who want an exclusive, story-rich evening.
8. Chicago to Milwaukee: Day Trip with Brewery Tour & City Highlights
Finally, the Chicago to Milwaukee: Day Trip combines a scenic journey with brewery visits on an 8- to 10-hour tour. You’ll see Milwaukee’s Miller Brewery, explore the Harley-Davidson Museum, and visit the Milwaukee Art Museum and Public Market. This full-day excursion is perfect for culture, craft beer, and art lovers wanting an extended experience.
The highlight is touring the Miller Brewery, where you can enjoy samples and learn about beer production. The tour’s long duration makes it ideal for those who enjoy comprehensive trips with multiple activities. Reviewers note the professional guides and well-organized itinerary.
At $125, it’s a good value for a full day of sightseeing and brewery tasting outside Chicago. It’s best suited for travelers comfortable with long days and diverse interests.
Bottom Line: Great for those wanting a full-day adventure combining culture, craft beer, and scenic views in Milwaukee.
How to Choose the Perfect Drinking Tour in Chicago
When deciding among these options, consider your budget, time available, and interests. For a lively, social experience, the Craft Brewery Tour by Barrel Bus provides VIP access and a fun vibe. If you’re more into history and local character, the River North pub walk or the Logan Square brewery tour are excellent choices. Want a food and beer combo? The Chicago Local Brewery Expedition delivers tasty bites with craft brew tastings.
For a special evening, the Private Speakeasy Crawl combines storytelling with hidden bars, perfect for couples or groups seeking an immersive experience. If a day trip is what you crave, the Milwaukee adventure offers a full day of sightseeing and brews.
Timing and availability can be tight, especially for the most popular tours, so booking early is recommended. Also, check if you prefer walking tours, bus experiences, or private outings—each offers a different vibe and level of comfort.
Final Thoughts
Chicago boasts an impressive range of drinking experiences, from craft brewery tours and historic pub walks to speakeasy crawls and even day trips to Milwaukee. For beer lovers, the craft brewery by Barrel Bus offers a lively, VIP experience, while history buffs may prefer the historic pub tour.
If you want a mix of culture, history, and good drinks, any of these tours will enrich your stay. Just remember to book early, especially for popular options, and enjoy Chicago’s rich drinking culture—one glass at a time.