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Chicago Twenty Something |

Chicago Twenty Something throws the best holiday events, tasting festivals, bar crawls, booze cruises, and tons more! Some of our most popular events include: The Mustache Crawl, Nova New Year's Eve, Chicago Whiskey Festival, Chicago Shamrock Crawl, Chicago Wine Fest, Chicago Donut Fest, and Chicago Country Crawl!


Want to celebrate your birthday at one of our events? Email us at and we can get you a free ticket and an awesome deal for your friends!


Event Ambassadors Wanted!  Earn FREE tickets and cash for spreading the word & bringing your friends out to our events.  Email for more info


Be sure to click the "Follow" button below to stay up to date with all of our upcoming events! Also, you can join our VIP list for exclusive discounts on tickets by clicking HERE.

Sorry, there are no upcoming events