Windy Pillows
Description: Part of a series I did in which I incorporated modern cartoon characters inside classical paintings to look fit the style and scenario of the painting. The saturation, color balance, blending, and shading of both the cartoons and paintings were changed so both fit well with each other as if they were originally part of the artwork.
Description: A bold illustration of a powerful bear inspired by Chicago football vibes and the toughness of the Windy City. This football bear design captures strength, tradition, and classic gridiron energy, making it perfect for football fans, streetwear lovers, and anyone who enjoys strong animal mascot artwork. A timeless sports-inspired design that stands out on game day or everyday wear.
Chicago Bears Mascot Windy City Game Day Spirit #5508 Pillow
by Spirit of Change
$23 $28
Description: Well shit, a skeleton ghost sheet caught in windy Halloween night, bringing spooky humor with a ghostly sheet, skeleton, and breezy haunted scene. A funny seasonal phrase adds a playful twist to the very eerie Halloween mood for fans of spooky humor. Funny Halloween skeleton ghost sheet theme for spooky humor fans who enjoy windy ghost scenes and a playful well shit phrase. The odd sheet and skeleton create a light haunted mood suited to anyone drawn to simple ghostly Halloween humor and fun too
Well Shit Skeleton Ghost Sheet Halloween Windy Spooky Humor Pillow
by Sheila Galaxy
$23 $28
Description: Bring gritty ice tradition to the streets with this Chicago hockey crossed tomahawks splatter design. Featuring a heavily weathered 'C' crest layered over bold crossed tomahawks with paint-drip distress in classic red, yellow, and green accents, this graphic is built for United Center tailgates, Windy City puck faithful, and standout sports streetwear rotations.
Description: WMET originally hit the air on March 9, 1959, as WDHF, owned by Hi-Fi systems and record store owner James DeHaan. Its call sign stood for DeHaan Hi-Fi and operated out of DeHaan's store in Evergreen Park, Illinois with its transmitter and tower in Oak Lawn. The station was primarily an easy listening format and would eventually go to a Top 40 model after changing ownership a few times. In 1976, the station's call letters were changed to WMET, while retaining its top 40 format and by 1979 had embraced an album-oriented rock (AOR) format.
Description: Celebrate the excitement of the 2026 All-Star Game with this bold basketball fan design inspired by the Windy City. Featuring a vintage gothic typography style and a striking sports aesthetic, this graphic is perfect for basketball fans, collectors, and anyone looking to commemorate the 2026 season. Great for t-shirts, hoodies, stickers, mugs, and more.
Fever Girls Windy City 2026 All-Star Game Basketball Fan T-Shirt Pillow
by angelaru
$23 $28
Description: Celebrate your love for Chicago and its famous culinary delight with this unique hot dog flag design. This graphic reimagines the classic Chicago flag, substituting the traditional red stars with four mouth-watering red frankfurters nestled in buns. The design maintains the iconic white and light blue horizontal stripes, creating a humorous and recognizable symbol of the Windy City. This apparel is ideal for Chicago residents, foodies, and anyone who enjoys a classic Chicago style hot dog. Whether you're a local hot dog enthusiast or a visitor who fell in love with the city's street food, this design is a fantastic way to showcase your appreciation. It's a fun conversation starter for gatherings, casual outings, or just everyday wear. Embra
Spooky Chicago Football Good Better Best Halloween Bear Graphic Pillow
by Bastian
$23 $28
Description: Show your Windy City pride! This minimalist Chicago coordinates design is the perfect gift for locals, tourists, and Illinois travelers. Get your awesome Chicago vacation souvenir today!
CHICAGO 41.8781 N 87.6298 W - Chicago Minimalist City Pride MAY-130 Pillow
by Animangapoi
$23 $28
Description: A design I made as a Cubs fan - they're so up and down :). SCROLL DOWN for the design on other products like hoodies, stickers, magnets, mugs, etc.
Chicago Baseball - Windy City - We Only Stink Sometimes Pillow
by Chicago Sport & Design
$23 $28
Description: Celebrate legendary Windy City ice hockey tradition with this retro gradient style Chicago hockey design. Featuring 90s vintage lettering, iconic hockey vibes, and Original Six founding details, it is perfect for Chicago fans, United Center game days, and lovers of classic streetwear hockey culture.
Description: Extra dipped and extra cute! This kawaii Italian beef sandwich character celebrates Chicago's most iconic savory street food treat
Cute Chicago Italian Beef Sandwich Kawaii Doodle Pillow
by Scribble of Happiness
$23 $28
Chicago STYX Windy Cities Tour Classic Rock Concert Pillow
by Matricula De Pro Studio
$23 $28
Description: Check out Bob After Dark's Nightmare at Navy Pier session of the Ghostbusters TTRPG, streaming straight from WonderverseChicago! Remember kids. If you're free this Saturday (10/19) and want to party at Wonderverse? They are streaming the event on their jumbo tron, and you can watch while playing games or sip on Ghostbusters inspired cocktails. If not, please watch the stream! If you're inclined? Make a donation. Every dollar helps. The Ghostbusters franchises and Bob After Dark are raising money for Extra Life via the Extra Life Chicago Guild. All profits from the sales of this design will go to Extra Life!
Bob After Dark Presents: The Ghostbusters TTRPG Live at Wonderverse Pillow
by Lionheartly
$23 $28
Description: A bold, detailed illustration of a cool bear wearing aviator sunglasses reflecting the Chicago city skyline, a knit pom-pom, and a striped in navy and gold — the ultimate Chicago pride graphic. This vintage-style bear art is perfect for Windy City locals, Midwest natives, and anyone who loves urban wildlife artwork with a retro flair. Makes a great gift for birthdays, holidays, or any Chicago enthusiast who wants to rep their city in style.
