Chicago Twenty Something
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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.
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
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)
Buckle up party animals! The Wrigleyville Halloween crawl is back and better than ever! Don’t wait to lock in your tickets - $10 early bird 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!
09/29/2026
Showed our support for breast cancer research on Day Time Chicago this morning! 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👙🍒💓
✨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 CHI20FB for a discount!
09/28/2026
And you know what, wearing a wig and singing All I Want For Christmas the minute November 1st hits is good for the soul🙂↕️ We’ll see you at the Wrigleyville Halloween Crawl on SATURDAY OCTOBER 31ST!
LIMITED $10 TICKETS ARE ON SALE NOW!
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!
wrigleyvi
Also, a costume with a weird little prop 🤌
Founding fathers is funny every time
She ATE with this midsommar look, nailed the Florence Pugh ☹️
Mid crawl glizzy hits different 🤌🌭
Everyone liking their costume at the same time is like seeing a shooting star
And ya know what, there’s nothing wrong with that
I can hear this costume
See you there🫡 DONT WAIT TO GET TOUR TIX!
Chicago weather has been so weird this year, for a second weekend in a row the wind blew me straight to Riverwalk Fall Fest and then it blew this fall cocktail right into my hand 🍂🍻🎃
Come see us 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
cFall Cocktails & B**r
🍎Apple C***r Donuts
🎃Pumpkin Patch
📸Photo Ops
🍁Fun for all ages! (21+ to drink)
🎯Games & more!
🔗IPHFallFest.com
Sampling different espresso martini flavors all day is actually my dream☕ See you at Hubbard Inn Espresso Martini Fest, NEXT SATURDAY, October 3rd!
Tix include 15 tastings, giveaways & more!
Use promo code CHI20IG for a discount!
LINK IN BIO for tix
Plans set early so I can focus on my costume 🙂↕️👻 Halloween is on a Saturday this year, don’t wait til the last minute to set your plans! Spend Halloweekend with us⬇️
Friday 10/30 - Halloween at Old Crow
‼️LIMITED $5 SUPER EARLY BIRD TIX ON SALE NOW!
🔗ChicagoHalloweenTix.com
🎟️Tix include admission, a drink, a shot and live band! Party at Wrigleyville’s # 1 Country bar—costumes, boos & booze await
Saturday 10/31 - Wrigleyville Halloween Crawl
‼️LIMITED $10 SUPER EARLY BIRD TIX ON SALE NOW!
🔗WrigleyvilleHalloweenCrawl.com
🎟️Tix include:
👻admission
🍽️Free dinner buffets
🍻Gift cards and more!
USE PROMO CODE CHI20IG for a discount!
wrigleyville
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