Chicago’s 8 Best Drinking Tours (With Prices & Reviews)

Chicago’s lively bar scene and innovative craft breweries make it a perfect city for exploring with a drink in hand. Whether you’re after a lively brewery tour, a historic pub crawl, or a scenic boat cruise with tropical cocktails, Chicago offers a range of options that suit different styles and budgets.

We particularly enjoy the Chicago Craft Brewery Barrel Bus Tour for its blend of behind-the-scenes brews and fun transportation, as well as the historic pub walking tour that immerses you in local history and classic taverns.

These tours give you a chance to experience Chicago’s drinking culture beyond just ordering at the bar—they’re about engaging with local stories, discovering hidden spots, and tasting distinctive drinks.

In this guide, we’ll walk you through the eight best drinking tours in Chicago, each offering a unique way to enjoy the city’s renowned beer, spirits, and lively bar scene. From lively bike adventures to scenic river cruises, there’s something here for every type of drinker.

1. Chicago Craft Brewery Barrel Bus Tour

At number one, the Chicago Craft Brewery Barrel Bus Tour stands out for its combination of craft beer appreciation and a stylish, retro transportation experience. Traveling aboard a traditional Prohibition–style barrel bus, this tour takes you to some of Chicago’s lesser-known breweries, avoiding the crowded tourist spots.

The focus here is on small-batch and innovative breweries, with several behind-the-scenes production facility tours that reveal the science of brewing.

Guests rave about the knowledgeable and friendly guides, with reviews highlighting the fun atmosphere and plentiful beer samples. The tour lasts about 3 hours 45 minutes and costs around $99.60 per person. It’s ideal for those curious about craft beer, whether you’re just starting out or already a seasoned connoisseur.

The route also offers the chance to meet fellow beer lovers in a relaxed setting, with plenty of tastings and educational insights.

Bottom Line: If you want a lively, entertaining way to explore Chicago’s craft scene without the hassle of driving, this barrel bus tour offers great value and a memorable experience.

2. Chicago: Craft Brewery Tour by Barrel Bus

Coming in just behind the top spot, this tour provides a more extended, four-hour experience exploring Chicago’s hippest breweries aboard a barrel-shaped bus. It features a VIP behind-the-scenes tour of a top nano-brewery, which is a highlight for craft beer enthusiasts.

This tour is particularly known for uncovering the secrets of craft brewing in Chicago and for its lively group atmosphere, where you can play interactive party games.

With a rating of 4.9/5 from 50 reviews and a cost of $100, this tour offers a slightly longer and more immersive experience. The focus on small-batch brews and local brewing techniques makes it a hit for those interested in the artistry behind the beer. The group size tends to be friendly and social, perfect for making new friends while sampling some of the most innovative beers in the city.

Bottom Line: This tour is excellent for craft beer fans who crave a VIP, behind-the-scenes look coupled with fun group activities and tastings.

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

For a more leisurely, cultural experience, the Walking Tour of Historic Chicago Pubs offers a chance to explore four of the city’s most iconic taverns.

It’s a 3.5-hour guided walk through the Loop and River North neighborhoods, starting with the Marquette Building and visiting legendary spots like The Berghoff Restaurant, Brehon Pub, and The Green Door Tavern. You’ll learn about Chicago’s evolving history and how its drinking culture fits into the broader story of the city.

The tour costs $65 per person and is rated perfect 5/5 by a small group of reviewers. It’s ideal for history buffs or those who prefer a more relaxed, conversational style of exploration. Each pub has its own story, from the oldest operating restaurant to secret speakeasies, making it a rich, storytelling experience. You’ll also appreciate the walk’s scenic route past notable landmarks.

Bottom Line: Best suited for those interested in Chicago’s history and culture, this tour combines storytelling with visits to historic pubs—perfect for a laid-back afternoon.

4. Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

If you prefer an active day with a culinary twist, this bike tour offers a mix of sightseeing and tasting Chicago’s iconic foods. Covering neighborhoods like the Gold Coast, Lincoln Park, and the lakefront, you’ll cycle past stunning architecture, lush parks, and bustling streets.

Along the way, you’ll stop at famous spots such as Lou Malnati’s Pizzeria for authentic deep-dish pizza and the Wiener’s Circle for hot dogs, plus a cupcake stop and a beer tasting.

This 4-hour tour is priced at $179, and while it’s the most expensive on our list, it offers a full sensory experience blending exercise, history, and food. The guide caters to all fitness levels, making it accessible for most travelers. Guests love the combination of scenic views, lively neighborhoods, and the chance to sample Chicago’s food culture on two wheels.

Bottom Line: Perfect for active foodies who want to see the city’s highlights and indulge in classic Chicago eats.

5. Chicago: Milwaukee City Highlights Day Trip with Brewery Tour

For those interested in a broader experience, this day trip to Milwaukee combines city sights with brewery visits. The tour includes stops at the Harley-Davidson Museum and Miller Brewery, with insightful tours and tastings. It also visits the Milwaukee Art Museum and Public Market, making it a comprehensive cultural and craft beer adventure.

At just over $100, the day trip offers a good balance of activities, with the added bonus of exploring a different city. The Harley-Davidson Museum is a standout, and the Miller Brewery tour offers a deeper dive into brewing history. Reviewers mention the tour as very professional, with plenty of information and fun stories.

Bottom Line: Best suited for travelers who want a full day of culture, history, and beer, with the convenience of an organized trip outside Chicago.

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

This full-day tour emphasizes Milwaukee’s art and brewing scenes, with visits to the Milwaukee Art Museum, Miller Brewery, and the Harley-Davidson Museum. It also offers some free time at the Milwaukee Public Market, a great spot for local eats. The tour lasts around 8-10 hours and costs $125, making it ideal for those wanting a comprehensive look at Milwaukee.

The highlight is the stunning architecture of the Milwaukee Art Museum, especially the iconic wing-like structure. The Miller Brewery tour includes sample tastings, and the Harley-Davidson Museum showcases over 450 motorcycles. Reviewers mention the tour as professional and informative, appealing to those with a curiosity for industrial design and American craftsmanship.

Bottom Line: Perfect for travelers with a full day to dedicate to Milwaukee, especially if they’re keen on art, motorcycles, or beer.

7. Chicago Tiki Bar Cruise on Chicago River or Lake Michigan

Looking for something a little different? The Tiki Bar Cruise combines scenic views with tropical drinks. This 75-minute cruise on the Chicago River or Lake Michigan features tropical cocktails, beers, and wines, all served in a tiki-inspired setting complete with palm trees and thatch roofing.

Rated 3.8/5 from 15 reviews, this cruise offers a relaxed vibe with stunning city skyline views. It’s perfect for those who want a quick, fun escape without the full commitment of a long tour. You’ll cruise past landmarks like Navy Pier and enjoy the warm atmosphere of the tiki decor.

Bottom Line: A fun, light-hearted option for a quick drink with great views—ideal for a casual afternoon or evening outing.

8. Chicago Bar Crawl: Chi-Town Showdown

Finally, the Chi-Town Showdown is an app-led bar crawl offering a competitive and interactive exploration of Chicago’s bar scene. Priced at just $14.99, it’s a budget-friendly way to discover local bars, solve puzzles, and learn about the city’s nightlife.

As it currently has no reviews, it’s more suited for those who enjoy self-guided adventures with a gamified twist. The tour lasts about 1.5 hours and covers several bars, making it a quick and budget-conscious option. You’ll get to experience different atmospheres and maybe find your new favorite local spot.

Bottom Line: Great for travelers who enjoy a bit of friendly competition and want an inexpensive way to explore some of Chicago’s nightlife.

How to Choose the Right Drinking Tour in Chicago

When deciding between these options, consider your budget, how much time you want to spend, and what kind of experience appeals most. If craft beer is your thing, the Chicago Craft Brewery Barrel Bus Tour or the craft brewery tour by barrel bus are excellent choices.

Want a cultural experience? The historic pub walk combines history with drinks. Looking for a physically active day? The bike tour with pizza and hot dogs offers a fun mix of exercise and bites.

For those interested in exploring a city just next door, the Milwaukee day trips provide a broader perspective on Midwestern brewing and culture, with several tours (Milwaukee city highlights) offering a full itinerary. Finally, a quick, scenic tiki cruise or a budget-friendly bar crawl can round out your options if you prefer something relaxed or playful.

Remember to book early, especially for popular tours, and check if any upgrades or special dates are available. Whether you want a lively brewery bus experience or a historic pub walk, Chicago’s drinking scene has something for every taste.

Chicago’s bar scene and craft breweries make it a city where you can sample diverse flavors and stories. The options range from educational and immersive to casual and scenic. For craft beer lovers, the Chicago Craft Brewery Barrel Bus Tour offers an engaging behind-the-scenes look, while history fans may prefer exploring the city’s storied pubs.

Active travelers will enjoy the bike tour with pizza and hot dogs, a great way to see the city and indulge in its famous eats. Whatever your preference, these tours promise a memorable way to experience Chicago’s lively drinking culture.