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.

A little Fall Fest photo dump to make this rainy Monday feel more cozy than icky🍻🍂 Riverwalk Fall Fest is BACK for anoth...
08/31/2026

A little Fall Fest photo dump to make this rainy Monday feel more cozy than icky🍻🍂 Riverwalk Fall Fest is BACK for another year Island Party Hut !

🚨Early Bird Tix Start at $5! + Use promo code CHI20IG

Tickets include:
🍁Admission
🍻Welcome shot (for those 21+) or drink (Fall Shirly Temple, Apple Cider or Hot Chocolate)
🎸Live Music from 1-4pm & 5-8pm
📸Photo Ops
🎯Games & more!

Event also features:
🎸Live Music from 1-4pm & 5-8pm
🌽Hayrides on the River
🍻Fall Cocktails & Beer
🍎Apple Cider Donuts
🎃Pumpkin Patch
📸Photo Ops
🍁Fun for all ages! (21+ to drink)
🎯Games & more!

🔗IPHFallFest.com



A fall cocktail gates to see me coming🍎🍻

Vibessss🍂🎸

Fall on the riverwalk is really such a vibe

Oh you just like went to the pumpkin patch at Riverwalk Fall Fest?? My dream date…cute

Tickets start at only $5! Use promo code CHI20

08/28/2026

✨ 🕯️Manifesting all my girls be both hot and witty and whimsical this halloween✨ 🕯️ Show off your costume at the Wrigleyville Halloween Crawl ⬇️

‼️Tickets for the Wrigleyville Halloween Crawl are ON SALE NOW FOR JUST $10!!!

…and NO it is NOT too early to be thinking about Halloween! Halloween’s on a Saturday this year - get your plans booked now🫵

Tix include:
👻admission
🍽️Free dinner buffets
🍻Gift cards and more!

🔗WrigleyvilleHalloweenCrawl.com
🌟Code CHI20IG for a discount!

08/26/2026

Stay silly wrigleyville 🍻🧟 We’re ready to run it back at this year’s Wrigleyville Halloween Crawl!

‼️Tickets for the Wrigleyville Halloween Crawl are ON SALE NOW FOR JUST $10!!!

…and NO it is NOT too early to be thinking about Halloween! Halloween’s on a Saturday this year - get your plans booked now🫵

Tix include:
👻admission
🍽️Free dinner buffets
🍻Gift cards and more!

🔗WrigleyvilleHalloweenCrawl.com
🌟Code CHI20IG for a discount!

If you’re the friend who every one texts “so what’re we doing this weekend?” this is internship for you🫵 LINK IN BIO (& ...
08/26/2026

If you’re the friend who every one texts “so what’re we doing this weekend?” this is internship for you🫵 LINK IN BIO (& our story) for full listing!

Your post grad guide to Big 10 football in Chicago is here🏈 Happy college football season to all who celebrate🍻🏟️ ...
08/25/2026

Your post grad guide to Big 10 football in Chicago is here🏈 Happy college football season to all who celebrate🍻🏟️

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Chicago, IL

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