Chicago Twenty Something

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.

05/26/2026

T-60 days till the biggest bar crawl in Chicagoooo!!!!! Mark your calendar for the next Flash Sale happening Tuesday June 2nd at 12pm CST!! 

THE MUSTACHE CRAWL 2026 - SATURDAY JULY 25th
Tickets and info at TheMustacheCrawl.Com

Chicago’s BIGGEST bar crawl 👇
Ticket includes:
✨Admission
👕Official Crawl T-shirt
🍽️Breakfast Buffet
💫Gift Cards to use on the crawl
🥸A mustache
🍻Drink specials and more!
🎟️: TheMustacheCrawl.com for all ticket details! 

05/25/2026

This counts as being in touch with the outdoors… right? 🕺🍸Booze Cruise is up all summer long!

Afternoon, evening, and late night cruises available all summer long for every occasion. Enjoy a luxury yacht with full bars, dance floor & Chicago’s best DJs performing live!

The best part? Tix start at just $20 - use promo code CHI20 for an additional discount at ChicagoPartyBoat.com (LINK IN BIO!)

Our favorite day of the year could not come sooner 🤞🍻🥸 $22 Phase Three Tickets Flash Sale ends THIS WEEKEND so hurry and...
05/23/2026

Our favorite day of the year could not come sooner 🤞🍻🥸 $22 Phase Three Tickets Flash Sale ends THIS WEEKEND so hurry and grab your tix while you can!

THE MUSTACHE CRAWL IS BACK SATURDAY JULY 25th ‼️

Tickets and info at TheMustacheCrawl.Com

Chicago’s BIGGEST bar crawl 👇
Ticket includes:
✨Admission
👕Official Crawl T-shirt
🍽️Breakfast Buffet
💫Gift Cards to use on the crawl
🥸A mustache
🍻Drink specials and more!
🎟️: TheMustacheCrawl.com for all ticket details!

05/22/2026

Y’all mind if we get a little country? 🤠🎤🍻Grab your boots and meet us for Wrigleyville Country Fest on Saturday, August 22nd!

Tix include admission, a shot of whiskey, a country brunch buffet, live music & more!

Limited $10 Early Bird Tickets on sale NOW! Use code CHI20 for a discount!
LINK IN BIO (WrigleyvilleCountryFest.com)

05/21/2026

The trifecta 💓🥂🎤 Get ready for Mimosas & T-swift Rooftop Day Party at Old Crow Saturday, June 27th!

Tix include 3 hours of mimosas + all the Taylor music you can handle! With 4 varieties of mimosas to try + $5 Taylor shots!

Grab your early bird tix now for just $20! Use code CHI20 for a discount at Chicago20Something.com (Link in our bio!) Hurry before prices increase! 

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Chicago, IL

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