Chicago Twenty Something

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Chicago Twenty Something Chicago Twenty Something Inc. is a Marketing and Event Planning company that creates the best bar crawls, booze cruises, tasting festivals and more!

If you're a recent college graduate, young professional, or just someone looking to have some fun, Chicago 20 Something is your one stop shop for all things party in Chicago! We specialize in creating unique experiences to help you take full advantage of everything that Chicago has to offer, all with a drink in hand! We host the biggest and best events in the city for St. Patrick's Day, Halloween, New Year's Eve and more...not to mention the iconic Mustache Crawl that takes over the Wrigleyville neighborhood every summer. At Chicago 20 Something, we're all about giving Chicagoans the opportunity to create memories that last a lifetime with new and old friends at one of a kind events. Whether you're a born-and-bred Chicagoan or a newcomer to the city, our events provide the perfect opportunity to party it up with like-minded individuals and let loose in the notorious Chicago party scene. Join us as we experience the pulse of Chicago like never before.

11/04/2026

The world’s largest and most famous Christmas bar crawl is back for its 30th year in Wrigleyville! Join us for TBOX (Twelve Bars of Christmas) on Saturday, December 12th! 🧑‍🎄🎄🍻

LIMITED $10 early bird tix on sale now!
Use promo code CHI20IG for a discount
TBOXCrawl.com

Tickets include:
🍳Breakfast buffets
🍻Gift cards to use on the crawl
🎸Live music
🎄Giveaways and more!

Party all day in 12+ bars starting at 10am!

The group chat reunion we’ve all been waiting for🍻We’ll see you the Wednesday before Thanksgiving for THE TURKEY CRAWL  ...
11/03/2026

The group chat reunion we’ve all been waiting for🍻We’ll see you the Wednesday before Thanksgiving for THE TURKEY CRAWL - Wrigleyville’s Blackout Wednesday Bar Crawl!

‼️LIMITED $10 early bird tix now on sale ➡️ Use promo code CHI20IG for a discount!
LINK IN BIO (TheTurkeyCrawl.com)

📆Wednesday, November 25th

TICKETS INCLUDE:
✨Admission to all bars
🦃Free dinner buffets
🪩Gift cards to use on the crawl
🍻Drink specials
💫Giveaways and more!

11/03/2026

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Chicago, IL

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