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Chicago Twenty Something

Chicago Twenty Something

 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.

 

 

 

 

 

 

Taylor Swift Bar Crawl: Eras, Ex's and Everything Taylor primary image

Taylor Swift Bar Crawl: Eras, Ex's and Everything Taylor

Saturday at 12:00 PM

Wrigleyville's Best Bars

From $10.90

The Turkey Crawl - Wrigleyville's Blackout Wednesday Bar Crawl primary image

The Turkey Crawl - Wrigleyville's Blackout Wednesday Bar Crawl

Wed, Nov 25, 7:00 PM

Wrigleyville's Best Bars (Full List in Details)

From $10.00

Wrigleyville NYE 2027 Bar Crawl - Chicago's New Year's Eve Party | 10+ Bars primary image

Wrigleyville NYE 2027 Bar Crawl - Chicago's New Year's Eve Party | 10+ Bars

Thu, Dec 31, 7:00 PM

Wrigleyville's Best Bars TBA

From $10.00

Mac & Cheese Crawl - Chicago's Cheesiest Bar Crawl! Mac & Cheese Included! primary image

Mac & Cheese Crawl - Chicago's Cheesiest Bar Crawl! Mac & Cheese Included!

Sat, Jan 23, 11:00 AM

Wrigleyville's BEST Bars TBA

From $10.00

Old Crow's Country Day Party:  Live Band, Welcome Drink & Shot! primary image

Old Crow's Country Day Party: Live Band, Welcome Drink & Shot!

Sat, Mar 6, 12:00 PM

Old Crow Smokehouse

From $10.00

Chicago Shamrock Crawl - Wrigleyville's St. Patrick's Day Bar Crawl 25+Bars primary image

Chicago Shamrock Crawl - Wrigleyville's St. Patrick's Day Bar Crawl 25+Bars

Sat, Mar 13, 8:00 AM

Wrigleyville's Best Bars (Full List Below)

From $10.00

2027 Taylor Swift Bar Crawl: Eras, Ex's and Everything Taylor primary image

2027 Taylor Swift Bar Crawl: Eras, Ex's and Everything Taylor

Sat, May 1, 12:00 PM

Wrigleyville's Best Bars TBA

From $10.90

Wrigleyville Halloween Crawl - Chicago's BIGGEST Halloween Party primary image

Wrigleyville Halloween Crawl - Chicago's BIGGEST Halloween Party

Sat, Oct 30, 5:00 PM

Wrigleyville's Best Bars TBA

From $10.00

November 14Saturday
November 2026
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Taylor Swift Bar Crawl: Eras, Ex's and Everything Taylor primary image

Taylor Swift Bar Crawl: Eras, Ex's and Everything Taylor

Saturday at 12:00 PM

Wrigleyville's Best Bars

From $10.90

November 25Wednesday
The Turkey Crawl - Wrigleyville's Blackout Wednesday Bar Crawl primary image

The Turkey Crawl - Wrigleyville's Blackout Wednesday Bar Crawl

Wed, Nov 25, 7:00 PM

Wrigleyville's Best Bars (Full List in Details)

From $10.00

December 31Thursday
January 23Saturday
Mac & Cheese Crawl - Chicago's Cheesiest Bar Crawl! Mac & Cheese Included! primary image

Mac & Cheese Crawl - Chicago's Cheesiest Bar Crawl! Mac & Cheese Included!

Sat, Jan 23, 11:00 AM

Wrigleyville's BEST Bars TBA

From $10.00

March 6Saturday
Old Crow's Country Day Party:  Live Band, Welcome Drink & Shot! primary image

Old Crow's Country Day Party: Live Band, Welcome Drink & Shot!

Sat, Mar 6, 12:00 PM

Old Crow Smokehouse

From $10.00

March 13Saturday
Chicago Shamrock Crawl - Wrigleyville's St. Patrick's Day Bar Crawl 25+Bars primary image

Chicago Shamrock Crawl - Wrigleyville's St. Patrick's Day Bar Crawl 25+Bars

Sat, Mar 13, 8:00 AM

Wrigleyville's Best Bars (Full List Below)

From $10.00

May 1Saturday
2027 Taylor Swift Bar Crawl: Eras, Ex's and Everything Taylor primary image

2027 Taylor Swift Bar Crawl: Eras, Ex's and Everything Taylor

Sat, May 1, 12:00 PM

Wrigleyville's Best Bars TBA

From $10.90

October 30Saturday
Wrigleyville Halloween Crawl - Chicago's BIGGEST Halloween Party primary image

Wrigleyville Halloween Crawl - Chicago's BIGGEST Halloween Party

Sat, Oct 30, 5:00 PM

Wrigleyville's Best Bars TBA

From $10.00