Comedy & Craft Beer Walking Tour of Old Town
No matter the season, the weather, or the political climate, The Windy City has two unparalleled passions: beer and improv comedy. For over a century, Chicago has been churning out some of America’s all-time favorite comics and brews.
Join Bobby’s Bike Hike for a relaxing and fun afternoon exploring the laughter and local pours that this city has to offer! Let one of our entertaining and informative tour guides lead you and your group on this incredible Chicago brew tour. All Beer and Food samples included in ticket price.
Our Old Town Comedy and Craft Beer walking tour is perfect for friends, birthday parties, bachelor/bachelorette parties, guys’ or girls’ weekends, couples, or anyone looking to have a good time!
Please note, guests MUST be 21 years of age or older.
Enjoy One of the Best Brewery Tours in Chicago
Craft brewing has become a national obsession over the past decade. These independent operations put their time and money into developing distinctive flavors that delight their critics — you, the craft brew connoisseur. Whether you have been sampling craft beer for years or you only recently discovered this fun hobby, we can help you find the top spots in the city to enjoy a cold one with your friends. Our Chicago brewery tours highlight the best the area has to offer in craft beer.
Do you have college buddies in town for the weekend? Are there officemates you want to get together with outside of work? Are you looking for unique bachelor or bachelorette party ideas? Our brew tours of Chicago will make a memorable way to celebrate. Of course, you don’t have to be celebrating anything to go on one of our tours. We also make the perfect activity for a lazy weekend when you have nothing else on the schedule and want to do something fun.
Our Chicago brew tours can help you acclimate to the city when you visit, too. We recommend you take them early in your vacation or business trip. This way, you get a feel for the town and can identify any breweries you want to return to after sampling. Other benefits to going on our brewery tours in Chicago include:
- Getting exercise: Walking the town will keep you energized throughout the tour.
- Finding like-minded people: Everyone on our tour loves craft beer and the craft brewery mentality.
- Discovering new places: Whether you are a Chicago native or a visitor, you will find places you would not have found on your own.
This guided experience explores the historic Old Town neighborhood, as it was home to one of Chicago’s oldest brewers, Michael Diversey. This former artists’ colony is also home to one of the city’s most vibrant bar scenes, as well as our world-famous improv comedy theatres, such as Second City.
On this afternoon adventure, you’ll learn all about the city’s early brewers, Prohibition-era drinking, our brewing education institutions, and the creative men and women who brew beer in the Windy City today! What’s more, you’ll get the inside scoop about our legendary improvised comedy scene, which has bred the funniest television and movie stars for decades.
You’ll taste the creations of some of our favorite local microbreweries including Revolution, Half-Acre, Three Floyds, Two Brothers, and Begyle. You’ll also get a sample of some of the larger breweries with Chicago connections and origins, like Goose Island and Lagunitas.
The tour guide will lead you to some of Chicago’s most popular and historic bars that have made names for themselves for serving local brews and vibrant atmosphere. At each bar, you’ll sample a couple of our favorite Windy City beer creations, and learn a bit about the history of the brewery and the watering hole. You’ll be drinking in the same spots as your favorite comics from Saturday Night Live, Ghostbusters, Wayne’s World, The Blues Brothers, 30 Rock, and more!
Further, your guide will serve as a recommendation expert, offering local insight into the best places to drink after the tour is over. They will be able to recommend similar beers based on favorite flavors, and provide information about the best Chicago beer and food pairings. They’ll also suggest the best current comedy shows, ensuring your entire stay in Chicago is filled with laughter and fun.
The tour lasts about two and a half hours, and walks at a relaxed but active pace. After this incredible Chicago brew tour, you’ll know why Bobby’s Bike Hike is the best way to see and taste Chicago!
What To Expect
Old Town is one of Chicago’s most historic North Side neighborhoods. Beloved by beatniks in the 1950s and 60s, and hippies in the 70s, Old Town is now a quiet, tree-line arts district.
Second City is a world-famous improvised comedy theatre, known for breeding comedians that later appeared on Saturday Night Live.
Old Town Ale House is a neighborhood institution, and popular hangout for Second City performers, alum, and employees.
Burton Place is a local favorite, famous for tasty pub grub and the legendary Chicago Handshake.
Old Town Pour House is a vibrant sports bar and gathering spot, boasting one of the lengthiest tap lists in the city.
Judy Maxwell Home is a popular neighborhood boutique owned by actress Joan Cusack.
Official Chicago watering hole for alumni and fans of the Notre Dame Fighting Irish, Declan’s is a fun and exciting Irish pub during football season and all year long.
Opened in 1888, Glunz Tavern is one of the oldest drinking establishments in the United States, famous for serving rare European beer and wine.
Zanies Comedy Club is Chicago’s premier place for traveling comedians, and a staple of Old Town.
Book Your Brewery Tour of Chicago With the Best Company Today
You have so many options for activities in Chicago. Why should you make time for the Bobby’s Bike Hike tour of Chicago breweries? For one thing, we know our stuff! We understand the craft beer devotee’s desire to try new things and seek out new places. We tailor the tour to these desires, and you will get a great sampling across a range of different locations. Each beer you sample will have its own unique flavor and appeal. Other reasons to book with Bobby’s include:
- We have been the top-rated Chicago tour company on Trip Advisor for 10 years running
- Chicago Reader named us the city’s most organized tour company
- You receive the best price when you book in advance online
- Mentions in national publications such as Midwest Living and National Geographic
Our tours provide a convenient option to drink your way across the city, enjoying the company of friends and family. Sign up for Bobby’s Bike Hike Chicago brew tour today.
Plus Beer From…
Half-Acre is a smaller up-and-coming brewery located on the North Side, gaining distribution momentum and popularity every year.
Goose Island has become a goliath American brewing company, but it boasts deep roots in the Chicago community.
Revolution Brewery is an extremely popular mid-size taproom, located in the artsy Logan Square neighborhood. Their beers can be found on draft all over the city, iconic for their fisted tap arms.
Three Floyd’s is an ever-expanding brewery in nearby Munster, Indiana, famous for their punk rock vibe and creative beer recipes.
Begyle is a microbrewery and taproom located on Chicago’s North Side, serving up flights, pints, and friendly atmosphere.
What Our Customers Are Saying“I’d recommend this tour to anyone, you will not be disappointed. Funny, entertaining stories and we tried some of Chicago’s delicious beers which was a treat for any craft beer drinker. And it was nice just being able to walk into each establishment and not have to use money as the tour includes all samples.”
– John L . Minneapolis, MN