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.

10/09/2026

Halloweekend is a marathon not a sprint😮‍💨 Kick the weekend off with us on Friday 10/30 for Halloween at Old Crow!

‼️LIMITED $5 SUPER EARLY BIRD TIX ON SALE NOW! USE CODE CHI20IG

🎟️Tix include admission, a drink, a shot and live band! Party at Wrigleyville’s # 1 Country bar—costumes, boos & booze await

🔗LINK IN BIO for tix & more info ( ChicagoHalloweenTix.com )

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10/09/2026

*gasp* who me? Im never in Wrigley and deeeeefinitely won’t end up there on Halloween 🫢 Keep it simple - spend Halloween at alllll your favorite spots on the Wrigleyville Halloween Crawl!

Saturday, October 31st
Wrigleyville Halloween Crawl - Chicago’s BIGGEST Halloween party🧟🍻👻

🔗WrigleyvilleHalloweenCrawl.com
🌟Code CHI20IG for a discount!

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

Get your tickets and get your costume 🫵 See you there!

Our love language is food so here’s a list of deals and specials for all our lovely marathon runners this weekend! Drop ...
10/08/2026

Our love language is food so here’s a list of deals and specials for all our lovely marathon runners this weekend! Drop a comment if you’ve got a favorite spot to add!👇

10/06/2026

My vibe is: pumpkin patches, corn mazes, warm cozy colors and apple c***r donuts🍎🍂 Only a few more Saturdays at Riverwalk Fall Fest left! Lock in your tickets early - You won’t want to miss out ;)

Riverwalk Fall Fest
Every Saturday this fall Island Party Hut now through October 31st!

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

Tickets include:
🍁Admission
🍻Welcome shot (for those 21+) or drink (Fall Shirly Temple, Apple C***r 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 & B**r
🍎Apple C***r Donuts
🎃Pumpkin Patch
📸Photo Ops
🍁Fun for all ages! (21+ to drink)
🎯Games & more!

🔗IPHFallFest.com

10/06/2026

On Saturdays we wear our bra out to a bar crawl support breast cancer research💅 Join us Saturday, October 17th for the Bra Crawl!

🍒A bar crawl where proceeds go toward breast cancer research! Come out and show your support by wearing a bra over your shirt👙🍒💓

‼️LIMITED $10 tickets on sale now!

✨Tix include admission to all bars, a brunch buffet, 2 welcome shots, drink specials, giveaways & more! Show your SUPPORT!

🩷A portion of proceeds will benefit breast cancer research

BraCrawl.com for tix & info
Use promo code CHI20IG for a discount!

‼️PRICES INCREASING TODAY‼️ The Wrigleyville Halloween crawl is back and better than ever! Don’t wait to lock in your ti...
10/05/2026

‼️PRICES INCREASING TODAY‼️ The Wrigleyville Halloween crawl is back and better than ever! Don’t wait to lock in your tickets ASAP! $15 tickets wont last forever👻

Come party with us Saturday, October 31st at Chicago’s BIGGEST Halloween party🧟🍻👻

🔗WrigleyvilleHalloweenCrawl.com
🌟Code CHI20IG for a discount!

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

Get your tickets and get your costume 🫵 See you there!

10/02/2026

Of course we’re gonna get a fall cocktail why would you even ask that🍻🍎 See you at Riverwalk Fall Fest this weekend!

Riverwalk Fall Fest
Every Saturday this fall Island Party Hut now through October 31st!

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

Tickets include:
🍁Admission
🍻Welcome shot (for those 21+) or drink (Fall Shirly Temple, Apple C***r 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 & B**r
🍎Apple C***r Donuts
🎃Pumpkin Patch
📸Photo Ops
🍁Fun for all ages! (21+ to drink)
🎯Games & more!

🔗IPHFallFest.com

10/01/2026

Sing your heart out at the Taylor Swift Bar Crawl on Saturday, November 14th!

Tickets include admission to all bars on the crawl, a free brunch buffet, gift cards to use on the crawl, Taylor themed drink specials, all the Taylor Swift music you can handle, giveaways & more!

Limited $10 early bird tickets are on sale now! Use code CHI20IG for a discount
LINK IN BIO! (ChicagoSwifites.com)

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Chicago, IL

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