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ChiTribe Business of the Month: Chicago Twenty Something

Let’s meet Freddie Kole, founder, and owner of Chicago Twenty Something.

ChicagoTwentySomething.com and its affiliate sites and companies are Marketing and Event Planning companies that act as a social network for those in their 20’s who work, live, or play in the city.

Chicago Twenty Something Website

A Northbrook native, Freddie has been connecting young professionals throughout the city for the last twenty years. Now Freddie has grown his business and they have hundreds of events throughout the city. ChiTribe loves working with Freddie and we are excited to profile the great work he does. Learn more about ChiTribe Business of the Month and nominate your friends.


Where are you from?

Northbrook, IL 

Where did you go to school? 

University of Illinois Urbana-Champaign

Freddie Cole ChiTribe Business of the Month Chicago Twenty Something

What is Chicago Twenty Something? 

We produce and advertise social events that target those in their 20s and 30s. We put together everything from bar crawls and booze cruises to Adults Only Nights at Lincoln Park Zoo and Altitude Trampoline Park! Check out their website>>

When did you found Chicago Twenty Something?

I started the company in 2004 because I noticed there were several companies promoting nightclubs, but no one was producing events that targeted recent grads and young professionals.

Freddie Cole ChiTribe Business of the Month Chicago Twenty Something

What kind of events do you plan? 

We throw dozens of events throughout the year, but some of my favorites include the Chicago Shamrock Crawl, The Mustache Crawl, Chicago Wine Fest, Chicago Donut Fest, Adults Night Out at Lincoln Park Zoo, our 20 New Year’s Eve Parties and of course Matzo Bash!

What is the most fun Jewish event you have worked on?   

Matzo Bash for sure. We’ve been throwing Chicago’s Annual Christmas Eve Party Since 2004 and it has been great to see it evolve over the years.  We’ve been fortunate to team up with great organizations such as JUF, FIDF, ChiTribe, Reboot, The JCC, and Shorashim. This is a great event to help raise money for each organization while providing a great option for Christmas eve.

Learn more about the Origin of the Matzo Bash


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