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Our Comedy and Craft Beer Pub Crawl of Old Town tour is currently unavailable. During this time, we’d recommend our Chicago Favorites Food Tour or our Bikes, Bites and Brews of Chicago Tour — each of which offers a craft beer sampling option.

Chicago Craft Beer & Comedy Clubs

Comedy & Craft Beer Pub Crawl / 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 evening or afternoon beer tour exploring the laughter and local pours that this city has to offer! Let one of our entertaining and informative local 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 pub crawl and 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.

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 of Chicago craft beer 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.

Group raising glasses on our Comedy & Craft Beer Tour of Chicago
Old Town Chicago Drinking Tour
Old Town Chicago Food Tour
Group Drinking Tours with Bobby's Bike Hike

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

Comedy & Craft Beer Pub Crawl of Old Town

Duration: 2.5 hours
Length: 1 mile
Level: Easy
Schedule: 7:30pm Fridays / 2:30pm Saturdays
Age: 21+

(Discount Online Rate includes Beer & Snack Samples)

Price: Fri-Sun Mon-Thurs
Adults (21+ Only) $52.99 N/A

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Private Tour