Chicago is a city that loves its drinks almost as much as it loves its architecture and deep-dish pizza. From innovative craft breweries to historic pubs, the Windy City offers a variety of drinking tours that reflect its lively character and rich local culture. We particularly appreciate the Chicago Craft Brewery Barrel Bus Tour because it combines an authentic, Prohibition-era style with behind-the-scenes brewery visits — a fun way to explore Chicago’s burgeoning craft beer scene. Meanwhile, the Walking Tour of Historic Chicago Pubs offers a more intimate, cultural snapshot of the city’s tavern history, perfect for those who like a good story with their drink. Whether you’re a beer enthusiast, a history lover, or just looking for a lively night out, Chicago’s drinking tours deliver on experience and flavor.
Quick Overview
Our list includes a range of drinking experiences that cater to different tastes and schedules. For craft beer lovers, the Chicago Craft Brewery Barrel Bus Tour and Chicago: Craft Brewery Tour by Barrel Bus offer visits to local breweries with behind-the-scenes looks and plenty of tastings. For history and culture enthusiasts, the Walking Tour: Historic Chicago Pubs in River North and the Loop explores renowned pubs with stories that bring Chicago’s past to life. Want to enjoy the water? The Tiki Bar Cruise on Chicago River or Lake Michigan combines beautiful sights with tropical drinks. For a full-day adventure, consider the Milwaukee Day Trip with Brewery Tour, which takes you across state lines for a mix of motorcycle, art, and beer culture. Plus, there’s a fun, casual Bar Crawl: Chi-Town Showdown if you prefer a quick, app-led pub-hopping experience.
1. Chicago Craft Brewery Barrel Bus Tour
Starting right in the heart of Chicago, the Chicago Craft Brewery Barrel Bus Tour offers an immersive experience into the city’s thriving craft beer scene. This half-day tour takes you aboard a vintage Prohibition-style barrel bus, adding a nostalgic charm to the outing. Your guide will lead you to several local breweries that you’re unlikely to find on your own, often away from the typical tourist spots. The behind-the-scenes tours of brewing facilities reveal the science and craft behind each pint, making it particularly appealing for those curious about how their favorite beers are made. Throughout the 3-hour 45-minute experience, you’ll sample a generous selection of beers, from IPAs to stouts, all included in the price.
Tour guide Ted earns high praise for his mix of humor and knowledge, with reviews calling him “fantastic” and “friendly.” The tour’s value lies in the combination of unique breweries, ample tastings, and the fun of traveling in style. It’s perfect for craft beer novices and aficionados alike, especially since no one has to worry about driving. The only potential downside is traffic that can make the day feel a bit rushed, but overall, it offers a well-rounded taste of Chicago’s craft scene.
Bottom Line: If you’re into craft beer and want to explore Chicago’s lesser-known breweries in style, this tour offers fun, education, and plenty of samples at a reasonable price.
2. Chicago: Craft Brewery Tour by Barrel Bus
At number 2, the Chicago: Craft Brewery Tour by Barrel Bus provides an exciting ride through the city’s most popular microbreweries and nano-breweries. For around $100, you get a 4-hour journey that highlights Chicago’s innovative brewing culture. This tour includes VIP behind-the-scenes access to one of the city’s best nano-breweries, offering an exclusive look at the craft and creativity involved. The bus itself is shaped like a barrel, adding to the fun and quirky atmosphere, and the group plays interactive games to keep the energy lively. The reviews mention the friendly group and the “fun day out,” making it clear this is a lively social experience.
What makes this tour stand out is the combination of local brewery visits and the personal VIP tour, which isn’t typical on most beer tours. The guide’s knowledge about Chicago’s craft scene adds depth, and the overall vibe is relaxed yet engaging. It’s an excellent choice for those wanting a taste of Chicago’s craft innovations coupled with a friendly, party-like atmosphere.
Bottom Line: For a lively, behind-the-scenes look at Chicago’s cutting-edge craft brewing, this tour combines education with fun, making it ideal for those who want a full afternoon of beer discovery.
3. Walking Tour: Historic Chicago Pubs in River North and the Loop
For a more intimate exploration, the Walking Tour of Historic Chicago Pubs offers a deep dive into the city’s pub culture while also showcasing its architecture and history. This small-group tour focuses on four atmospheric taverns, including the oldest operating restaurant in Chicago and a storied media watering hole. The tour begins in the afternoon at the Marquette Building, where your guide shares fascinating stories along the way. You’ll visit the inside of The Berghoff, enjoy a drink, and learn about its long history, then continue to pubs like Brehon Pub and The Green Door Tavern, which features a hidden speakeasy.
Guests love the personal touch of the guide’s storytelling, with reviews praising the “great stories” and “local insight.” The tour is perfect for history buffs or anyone interested in Chicago’s cultural past. The drinks are at your own expense, but the focus is on the environment and stories behind each place. The walking pace is moderate, and the tour lasts around 3.5 hours.
Bottom Line: If you want a relaxed, story-rich experience with local pubs and history, this walking tour combines culture and conviviality beautifully.
4. Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes, and Beer
Ideal for active travelers who want to combine sightseeing, local bites, and a bit of exercise, this bike tour covers Chicago’s neighborhoods in about 4 hours. Your friendly guide will lead you through the Gold Coast, Lincoln Park, and other iconic areas, stopping for some of Chicago’s most famous foods. First on the list is a visit to Lou Malnati’s Pizzeria to sample their legendary deep-dish pizza. Then, you’ll pedal through luxurious homes and admire skyline views, finishing with tasting hot dogs at The Wiener’s Circle and cupcakes at a popular bakery.
This tour is very highly rated, with the only review praising it as “great fun” and recommending it for its combination of sights and eats. It’s especially well-suited for energetic travelers who want a dynamic way to experience Chicago’s vibrant neighborhoods. The bike rental, food stops, and guided commentary make this a great value at $179, though it’s a bit pricier than other options.
Bottom Line: If you’re looking for a lively, food-focused adventure that blends physical activity with local flavors, this bike tour hits the mark.
$179.00 per person
5. Chicago: Milwaukee City Highlights Day Trip with Brewery Tour
Looking to extend your drinking adventures beyond Chicago? The Milwaukee Day Trip with Brewery Tour takes you to Wisconsin’s largest city, full of industrial charm and renowned breweries. The day begins with visits to the Harley-Davidson Museum and Milwaukee Art Museum, offering a mix of motorcycle history and stunning architecture. The highlight is the Miller Brewery tour, where you can sample different beers and learn about their brewing process. Once in Milwaukee, you’ll also explore the Public Market, home to 24 specialty vendors, perfect for grabbing a casual bite or drink.
This tour offers a well-rounded mix of culture, craftsmanship, and local flavor, with reviews mentioning the professionalism of the guide. The cost of $106 makes it an accessible way to experience another city’s beer scene while enjoying some of Milwaukee’s best sights.
Bottom Line: If a full-day, multi-faceted trip to Milwaukee appeals to you, this tour provides a taste of beer, art, and history in one convenient package.
6. Chicago to Milwaukee: Day Trip with Brewery Tour & City Highlights
For those wanting a longer, more comprehensive experience, this full-day tour blends Milwaukee’s highlights with beer culture. Starting with a ride from Chicago, the itinerary includes the Harley-Davidson Museum, Milwaukee Public Market, a Miller Brewery tour, and visits to the Milwaukee Art Museum. The tour lasts 8 to 10 hours, perfect for travelers who want to see a lot in one day. The architecture of the Milwaukee Art Museum and the history behind Harley-Davidson are particular standouts.
Reviews indicate that the tour is well-organized and engaging, especially for motorcycle fans and art lovers alike. The price of $125 offers value considering the full day’s itinerary, including multiple stops and guided commentary.
Bottom Line: For travelers with a full day, this tour balances culture, craft, and scenic views—ideal for those wanting an in-depth Milwaukee experience.
7. Chicago: Tiki Bar Cruise on Chicago River or Lake Michigan
If you prefer a relaxed vibe with scenic views, the Tiki Bar Cruise is perfect. For 75 minutes, you’ll cruise either the Chicago River or Lake Michigan on a tiki-themed boat, complete with tropical cocktails, beers, and wines. The boat’s design features palm trees and thatch roofs, creating a fun, laid-back atmosphere. The cruise offers a panoramic view of Chicago’s skyline and landmarks, making it a great way to unwind while taking in the city from the water.
Rated 3.8/5, the cruise appeals to those seeking a casual, social experience with the bonus of a full bar service. It’s especially good for a warm day or a special occasion. The main drawback is the shorter duration, so it’s best combined with other activities if you want a full day.
Bottom Line: For a breezy, tropical-themed break on the water with good drinks and views, this cruise fits the bill.
$41 per person
8. Chicago Bar Crawl: Chi-Town Showdown
Finally, the Chi-Town Showdown is an informal, app-led bar crawl designed for spontaneous fun and socializing. At just $14.99, it’s the most budget-friendly option and lasts around 1.5 hours, taking you through a selection of Chicago’s lively bars. While there are no reviews yet, it’s perfect for those who want a casual, flexible experience — especially if you’re traveling with friends and enjoy discovering local hangouts on your own schedule.
This tour is best suited for budget travelers or those who want to explore Chicago’s bar scene without a structured tour. It’s a good option if you want to customize your night or fit in multiple spots quickly.
Bottom Line: If you’re after an inexpensive, flexible pub-hopping experience, this bar crawl offers a straightforward way to enjoy Chicago’s nightlife.
$14.99 per person
How to Choose the Right Drinking Tour
Picking the best tour depends on your interests and schedule. If craft beer is your passion, options like the Chicago Craft Brewery Barrel Bus Tour or Chicago: Craft Brewery Tour by Barrel Bus are excellent. For a cultural, historic experience, the Walking Tour of Historic Chicago Pubs offers a more leisurely, story-driven outing. If water views and relaxed vibes are your thing, the Tiki Bar Cruise could be perfect. Budget travelers might prefer the Chi-Town Showdown bar crawl, while full-day explorers will enjoy the Milwaukee trips.
When booking, consider your energy levels, budget, and whether you want an active or laid-back experience. Most tours are popular during good weather months, so booking early is wise, especially for weekend slots.
To sum it up, Chicago offers a diverse selection of drinking tours — whether you’re into craft beer, historic pubs, water cruises, or casual pub crawls. The craft brewery tours stand out for their combination of education and fun, while the pub walk offers a cozy, story-rich experience. For a memorable water outing, the Tiki Bar Cruise hits the sweet spot. For those who want to explore a neighboring city’s scene, the Milwaukee trips provide a full-day adventure. Whatever your style, booking early guarantees a spot on these popular experiences, so pick your favorite and enjoy Chicago’s lively drinking culture.