Chicago Gay Pride Crewneck Sweatshirts

Chicago Pride with retro sticker motif

City of Chicago Flag featuring rainbow stars to celebrate gay pride, the Chicago Pride Parade and LGBTQ / LGBT / LGBTQIA pride month.

Chicago Pride Top

Show your pride with this Chicago skyline design

Show your pride for Chicago with this retro inspired design

Rainbow Flag for the City of Chicago. Gay pride parade, LGBTQIA Pride month, or just a great gift for that special someone.

LGBT Pride Rainbow flag with the City of Chicago's iconic stars from the Chicago flag.

Pride Chicago USA 2024

You're gonna need at least three shirts per day, so start shopping now! Happy Chicago Gay Pride 2023! You know Chicago will rock it! You will always find a fun shirt here! For you, for a gift, t-shirts, and more with a gay sensibility for the LGBTQ+ community and beyond. Quirky, naughty, minimalist, maximalist, retro, and modern--a little bit of everything. Loud and Proud? Proud and Understated? Yes! Click through and you’ll realize there is really something here for everyone. Daddy DD thanks you for all your support when buying these best-selling designs. Please come back regularly because there will be something new and different here.

I needed a pride shirt for the Chicago Gay Pride parade so I made a design for one!

"Celebrate your LGBT pride in a nostalgic way with our City Gay Pride retro shirt! This vintage design features a range of rainbow colors that represent the diversity and inclusivity of the LGBTQ+ community. The soft cotton garment has a worn and distressed look to give it that 70s or 80s style. Wear it to express your pride during pride parades or simply to add a pop of color to your wardrobe. This garment is a way to take your pride with you anywhere in style!"

Often described as the gay Cheers, Little Jim’s was the first gay bar in Boystown when it opened in 1975, making it the second-oldest gay bar in Chicago. In the early days, the bar had darkened windows to protect the safety of its customers. Within a few years of opening, more gay bars followed Little Jim's lead into the neighborhood. The divey, late-night spot became both a Boystown institution and one of the longest-running independently owned bars in the Chicago. A big part of the bar's legacy is that it was the first and only bar on Halsted Street to be fully integrated. Black, white, and Hispanic people all mingled and socialized there – literally everyone was welcome.

For the Chicago Lover on your Windy City Gift list who LOVES Diversity. Great Chicago Heartbeat Pride for the PROUD CHICAGOAN

Manhandler Saloon Vintage Gay Retro Leather Western

Chicago / Retro Style Faded Design

Mr. Leather Gay LGBT Vintage Retro

CHICACO RAINBOW CITY

Flaunt your Chi-town pride with this vintage, distressed design featuring a silhouetted skyline of Chicago.

Retro Defunct Touche Chicago Gay Nightclub

Chicago design promoting acceptance for the lgbtq and their friends!

Manhole Vintage Retro Leather Gay Chicago LGBT

Celebrate Freedom, Love and Diversity wearing this cool Chicago Pride Shirt. Awesome pride month design for lesbian, gay, transgender, queer, pansexual and bisexual men, women, boys, girls.

International Mr. Leather Vintage Retro Gay LGBT Chicago

Manhole Vintage Retro Leather Gay Chicago LGBT

International Mr. Leather Vintage Retro Gay LGBT Chicago

2132 N. Halsted St.

Gay Illinoisan

Chicago Gay Parade inspired design

Chicago - Retro Rainbow Typography Style 70s

by chromatosis design

by chromatosis design

Custom colorful DePaul Geometric Design

Show off your Land of Lincoln pride!

So. Are you hairy? You got some heft to you? You just like menacing woodland predators? If you answered yes to any of these questions, congratulations, it's another hoagiemouth design you need to own!

Designed with pride by JeeperJames

Bentwood chairs in the sequence of hues commonly described as making up a rainbow