Gay Chicago Posters and Art Prints

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

Chicago culture!

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.

Manhandler Saloon Vintage Gay Retro Leather Western

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

Chicago / Retro Style Faded Design

CHICACO RAINBOW CITY

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

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

Chicago Pride with retro sticker motif

Mr. Leather Gay LGBT Vintage Retro

Pride Chicago USA 2024

House music is electronic dance music first created in the early 1980’s by Dj’s in Chicago. The term ‘House music’ is from a club named ‘the Warehouse’ where the first house music was played by Frankie Knuckles.

Show your pride with this Chicago skyline design

"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!"

Chicago design promoting acceptance for the lgbtq and their friends!

Show your pride for Chicago with this retro inspired design

"HOUSE" Musik ist elektronische Tanzmusik, die erst in den frühen 1980er Jahren von Dj's in Chicago entstanden ist. Der Begriff "HOUSE" Musik ist aus einem Club namens 'the WAREHOUSE'.

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

by chromatosis design

by chromatosis design

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

2132 N. Halsted St.

Actor James Franco portrait using a No. 2 pencil by Chicago Artist Billy Jackson.

International Mr. Leather Vintage Retro Gay LGBT Chicago

Retro Defunct Touche Chicago Gay Nightclub

International Mr. Leather Vintage Retro Gay LGBT Chicago

James Franco Portrait using an ink pen by Chicago Artist Billy Jackson. Pen on paper #noeraser

Manhole Vintage Retro Leather Gay Chicago LGBT

Manhole Vintage Retro Leather Gay Chicago LGBT

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.

Gay Illinoisan

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.

Chicago - Retro Rainbow Typography Style 70s

Custom colorful DePaul Geometric Design

Designed with pride by JeeperJames