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Chicago Sweatshirts & Hoodies
1000+ items
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1000+ items
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Chicago Pride Illinois T-Shirt – Windy City Fan Tee | Uncle Jichuan Lightweight Sweatshirt
Uncle-Jichuan
$44.26
Chicago Premium Oversized Sweatshirt
JonysCreativeDesigns
$62.00
Big Apple of Chicago Skyline Minimalist Art Premium Oversized Sweatshirt
BoringClothes
$56.84
Vintage-Styled Bears Premium Oversized Sweatshirt
Daybreak Media
$62.00
UIC College of Medicine Premium Oversized Sweatshirt
Nicole Christine
$69.75
Blue Bear with Golden Face Premium Oversized Sweatshirt
maulanaansyh
$62.00
Payton #34. Chicago Bears Premium Oversized Hoodie
Primotees
$63.25
BERNIE MAC Premium Oversized Sweatshirt
Portraits by Billy H. Jackson
$62.00
Da Pope Malört & Savior Meme Design Premium Oversized Hoodie
BousinilyArt
$63.25
CHICAGO FIRE LOGO Pullover Hoodie
emilybraz7
$54.59
Last night a Dj saved my life from a broken heart. For house music djs. House music fans. Premium Oversized Hoodie
paulo silveira
$83.38
University of Chicago Premium Oversized Hoodie
Ellery Lapin
$83.38
CHICAGO P.D - DETECTIVE JAY HALSTEAD - INTELLIGENCE BADGE VEST Pullover Hoodie
emilybraz7
$54.59
Reader Logo Through the Years Premium Oversized Sweatshirt
The Chicago Reader
$62.00
Coach Ben Johnson Good, Better, Best Win Speech Art Pullover Hoodie
Bear Creative
$44.84
Fire, Med, PD skyline white Premium Oversized Sweatshirt
ellclark
$64.59
Chicago Park District (back) Lightweight Hoodie
adrien2297
$41.99
Oasis Soldier Chicago '25 Lightweight Hoodie
TraceTheFace
$44.09
University of Chicago Premium Oversized Sweatshirt
carolinezhao
$62.00
Chicago The Windy City Minimalist Art Design Premium Oversized Sweatshirt
BoringClothes
$56.84
Vintage Ice Man Caleb Williams Lightweight Sweatshirt
DakirooStudio
$46.19
Stellaride Premium Oversized Sweatshirt
atiredfangirl
$64.59
Connor Bedard Draft Art Premium Oversized Hoodie
B3 Graphics
$64.40
Ragtime Musical Hi-Res Premium Oversized Hoodie
blomdel
$77.63
Ferris Bueller at the Art Museum Premium Oversized Hoodie
comfysockz
$66.13
Loyola University Chicago Premium Oversized Sweatshirt
brooklevan
$63.92
The Chicago College, of Performing Arts Premium Oversized Hoodie
NoraroN
$69.00
Columbia College Chicago Classic Logo High Quality Print Premium Oversized Hoodie
blomdel
$77.63
Columbia College Chicago Flag Logo Premium Oversized Hoodie
hanhorton
$69.00
Filipino School of Chicago Premium Oversized Hoodie
Fil-School-Chi
$69.00
Chicago Blues Premium Oversized Sweatshirt
samhi113
$61.90
chicago fire cast-members Premium Oversized Sweatshirt
LondownDesign
$67.17
Original Chicagoland Beef Company Premium Oversized Sweatshirt
MalmoDesigns
$72.34
Chicago FC United logo usl Premium Oversized Sweatshirt
chcasey
$62.00
School of the Art Institute of Chicago Rainbow Gradient Logo Pullover Hoodie
Dennisust
$46.79
Chicago Flags with Teams and Skyline Premium Oversized Hoodie
kwald12
$66.13
Columbia College Chicago Premium Oversized Hoodie
blomdel
$77.63
Drose Day 1.4.25 Premium Oversized Sweatshirt
mysports
$67.17
Chicago Med tv show characters poster logo Premium Oversized Hoodie
AnsykD
$77.63
Chicago Football Heartbeat Pulse Premium Oversized Sweatshirt
Bored Imagination
$62.00
Joffrey Ballet Sign Chicago Premium Oversized Sweatshirt
Enzwell
$62.00
Decatur Staleys Premium Oversized Hoodie
Retrorockit
$69.00
End of Beginning Premium Oversized Sweatshirt
djokeerydaily
$62.00
SIX The Musical Queens Silhouettes— With Lyrics! Pullover Sweatshirt
broadway-babies
$41.94
Chicago Elevated Train Typography | The Loop City Skyline Art Premium Oversized Sweatshirt
SimplyJasper
$63.55
Chicago - The Musical/Movie Premium Oversized Hoodie
thefilmmagazine
$69.58
Chicago Bears Good Better Best by Coach Johnson on Colour Background Premium Oversized Hoodie
Bear Creative
$63.25
CHICAGO P.D - SERGEANT HANK VOIGHT - INTELLIGENCE BADGE VEST Premium Oversized Sweatshirt
emilybraz7
$72.34
CHICAGO MED - WILL HALSTEAD - SCRUBS - EMERGENCY MEDICINE Premium Oversized Hoodie
emilybraz7
$80.50
Chicago Fire Premium Oversized Sweatshirt
lemonlimeyogurt
$60.97
Chicago Cloud Gate Travel Art Illustration Premium Oversized Sweatshirt
BoringClothes
$56.84
Chicago the Musical Pullover Hoodie
Rasiadunn
$46.79
Marshall Field's Department Store Premium Oversized Sweatshirt
TeeArcade84
$64.59
CHICAGO FIRE CFD LOGO Premium Oversized Sweatshirt
emilybraz7
$72.34
House Music - Vintage Retro Hexagon Premium Oversized Sweatshirt
Jam Jar
$68.72
Vintage Wrigley Bleachers Premium Oversized Sweatshirt
frittata
$64.59
Chicago Park District Lightweight Hoodie
adrien2297
$41.99
School of the Art Institute of Chicago (SAIC) Premium Oversized Hoodie
HayleeC34
$63.25
SAIC School of the Art Institute Chicago Van Gogh Sunflowers Premium Oversized Sweatshirt
Katie Thomsen
$70.79
Joffrey Ballet Sign Night Premium Oversized Hoodie
Enzwell
$69.00
808 Premium Oversized Hoodie
trev4000
$77.63
Chicago Police Department Patch Premium Oversized Sweatshirt
LockedUp
$76.47
Chicago Fire - One Chicago Premium Oversized Hoodie
HumorStyle
$77.63
CHICAGO FIRE - LT. SEVERIDE - SQUAD 3 Premium Oversized Sweatshirt
emilybraz7
$72.34
Alex Caruso Mirror GOAT (Chicago) Premium Oversized Hoodie
RatTrapTees
$74.75
Fuck Fame Chicago Pullover Hoodie
TheLaw61
$47.96
CHICAGO P.D - DETECTIVE HAILEY UPTON - INTELLIGENCE BADGE VEST Premium Oversized Hoodie
emilybraz7
$80.50
Da Beers Premium Oversized Sweatshirt
Greg Dressel
$62.00
Barnaby's Family Inn Premium Oversized Hoodie
nwerlandson
$69.00
CHICAGO MED LOGO Premium Oversized Sweatshirt
emilybraz7
$72.34
Filipino School of Chicago White Logo Premium Oversized Sweatshirt
Fil-School-Chi
$62.00
Chicago PD Fire Med Premium Oversized Sweatshirt
HumorStyle
$69.75
Chicago Premium Oversized Hoodie
JonysCreativeDesigns
$74.75
Portillos Premium Oversized Hoodie
samanthaspratt
$69.00
Good Better Best Never Let it Rest - Chicago Bears Pullover Sweatshirt
Primotees
$41.94
mt joy - hippi van bus Premium Oversized Sweatshirt
LondownDesign
$67.17
Chicago Trains Map Premium Oversized Hoodie
Rich Anderson
$69.00
Chicago For Fans Premium Oversized Hoodie
CarKeeling
$69.00
Chicago Skyline Minimalist Blue Line Art Premium Oversized Sweatshirt
BoringClothes
$56.84
Polka will never Die Riding A Rex Harry Random Destruction Dresden Premium Oversized Hoodie
idwearit
$69.00
Columbia College Chicago Premium Oversized Sweatshirt
hanhorton
$62.00
CHICAGO MED - NATALIE MANNING - SCRUBS - EMERGENCY MEDICINE Premium Oversized Hoodie
emilybraz7
$80.50
PORTILLOS Premium Oversized Hoodie
Fridruiz19
$71.88
Good Better Best Chicago Bears Premium Oversized Hoodie
Miarsabhoul
$76.48
Vintage Columbia College Chicago Illinois Premium Oversized Hoodie
BackinDaysUni
$74.75
Delicious Chicago Pizza Premium Oversized Hoodie
harebrained
$71.88
And all that jazz, chicago the musical Premium Oversized Sweatshirt
PoppysMTPrints
$64.59
Marshall Field's Department Store Premium Oversized Hoodie
TeeArcade84
$71.88
Philadelphia International Records Premium Oversized Sweatshirt
goatboyjr
$62.00
Executive Producer Dick Wolf Premium Oversized Sweatshirt
Dennis Daniel
$62.00
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Chicago
Chicago hoodies and sweatshirts are expertly printed on ethically sourced, sweatshop-free apparel and available in a huge range of styles, colors and sizes. If you like your hoodies baggy, go two sizes up.
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