Chicago T-Shirts

Distressed Chicago Skyline Flag

Best paired with an ice-cold Old Style pilsner ––> Follow me on Instagram @hollowood.design

One of my favorite views on Western Avenue in Chicago.

Cub Style Vintage Chicago Gifts

Distressed Chicago flag red star.

Best Chicago

Hold on I'm outta beers, I'm gonna run to da Jewels.

Best Chicago

Defunct Chicago Whales/Feds Baseball 1913-1915

Chicago Flag Skyline T Shirts,hoodies and more.

Just a kid from Chicago

Show your love for the windy city

On July 12, 1979, 48,000 fans packed Chicago’s Comiskey Park for a doubleheader that included a promotion involving blowing up disco records. The event devolved into a fiery riot when crazed rock n' roll fans stormed the field as part of an anti-disco promotional event when a local disc jockey took the field between games to destroy the records listeners had brought. Once the crate of disco records had blown up, the crowd chanting 'DISCO SUCKS' cheered uproariously and began taking the field. From there they began throwing records and cherry bombs, tearing up the field and stadium facilities and otherwise devolving into an all-out riot that ended up with the Chicago PD riot squad being called in.

Vintage 773 Chicago Flag Gifts

An ode to The Bear: The Original Beef of Chicagoland. Distressed white version.

Retro Chicago Southside Irish t shirts,sweatshirts and more for men,women and kids.

Just a little hot dog from Chicago

Chicago Illinois Skyline and Architecture inspired design. Cityscape of the city. Perfect for travelers or locals.

Support the City of Chicago with this shirt. Features the Willis Tower as a text portrait!

The fictional Original Beef of Chicagoland serves as the primary setting of The Bear. It's a sandwich shop run by the Berzattos after the family patriarch started the place several years before the show’s events. The Italian beef joint is located in the River North neighborhood of Chicago and is popular among the blue-collar crowd on the city’s Near North Side, so it's safe to say that the restaurant has a rich cultural heritage in the city.

Legend of the Windy City crew, can now be up on your shirt! Features Benny the Bull, SouthPaw, Staley da Bear, Tommy Hawk and a Cubbie! All ninjafied! ENJOY! =)

Genuine reproduction of a Chicago Police patch.

Who has the best donuts? Chicago. This pastry guy hails from the city of broad shoulders.

The Chicago Cats was an American soccer club based in Chicago, Illinois that was a member of the American Soccer League from 1975 to 1976.

The 312 Area Code Numbers, with the Local sports logos representing local downtown Chicago Sports.

Vintage Chicago Flag Polish Eagle Heritage t shirts,hoodies and more.

The Windy City Chicago White Text

Chicago is the best city in America. This gem of the Midwest features such great sights as The Bean, The Loop, Millenium Park and more. Even if you hate deep dish pizza, you gotta love Chicago! The Chicago flag is distressed to give the shirt a vintage look. Makes a great gift for any Chicagoan!

Chicago inspired design.

Magikist was founded in 1943 by Wilbur "Bill" Gage, who changed the name of his Austin Rug Cleaners to Magikist, melding the words "magic" and "kissed." His wife at the time, Doris Greenwood, suggested the "sweetest name in rug cleaning" slogan and came up with the company logo, a pair of red lips. Gage operated Magikist in the Chicago area south of Howard Street and Lionel and Shirley Gelfand operated Magikist in the area north of Howard Street. In the Chicago area, the Magikist Lips (in the form of huge signs on the Edens Expressway, Dan Ryan Expressway, Kennedy Expressway, and Eisenhower Expressway which lit up and flashed) were well-known landmarks.

It's the Cell Block Tango, straight out of Chicago

This Chicago Irish Shamrock design makes a great gift for anyone and is perfect to wear around the house or out and about.

Captain Pancake is a huge fan of a certain team from Chicago!

Designed by a Chicano artist! Fueled by an odd Aqua Teen Hunger Force reference, a popular 70's group, and my desire to sport this shirt! Please enjoy a quote from the world's worst racist bootlegger: "OK guys, look, I'm sorry that I made an ass load of money sellin' these in the parking lot of your show. They ain't supposed to say "Chicano" it was them dumbass immigrants I had working for me. Anyways, I want you to have this." Bart Oates: "… $40 in change?"

Perfect gift for Windy City Lovers - T shirts, hoodies, notebooks, phone cases, coffee cups.

Fully restored vintage travel poster from California, USA. Please note that our posters are high quality reproductions based on professional, very high resolution scans of the originals. Our manual retouching process does not involve the use of filters that remove any original details or texture that you will see in the original prints. All details remain intact. Colors corrected. Imperfections removed.