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Chicago Sweatshirts & Hoodies
1000+ items
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1000+ items
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Vintage-Styled Bears Premium Oversized Hoodie
Daybreak Media
$69.00
Kanye West Dropout Bear Chicago Vintage Graduation Premium Oversized Sweatshirt
shopvinhcong
$72.34
Chicago Trains Map Premium Oversized Sweatshirt
Rich Anderson
$62.00
Chicago Blues Premium Oversized Sweatshirt
samhi113
$61.90
Dennis Rodmans Green Hair Worm Premium Oversized Sweatshirt
AbbelSwords
$62.00
Luther Burden III Choke Premium Oversized Sweatshirt
RatTrapTees
$56.84
Wizard Beer Pullover Sweatshirt
fanartdesigns
$43.69
Chicago CTA Sign Premium Oversized Sweatshirt
vellikhor
$62.00
Chicago Hockey Premium Oversized Sweatshirt
sashka1998
$60.45
Downtown Chicago City Skyline Walking Bear Silhouette Gift Premium Oversized Sweatshirt
Dressed For Duty
$62.00
Chicago Premium Oversized Hoodie
JonysCreativeDesigns
$74.75
BTS World Tour 2026 Arirang. CHICAGO. Premium Oversized Sweatshirt
EunsooLee
$62.00
Decatur Staleys Premium Oversized Hoodie
Retrorockit
$69.00
Goose Retro (Station Wagon) Premium Oversized Sweatshirt
in-verona
$62.00
Big Apple of Chicago Skyline Minimalist Art Premium Oversized Sweatshirt
BoringClothes
$56.84
Da Beers Chicago Bears Premium Oversized Sweatshirt
brandoen
$72.34
Historic Route 66 - The Mother Road - Santa Monica Premium Oversized Sweatshirt
NewNomads
$62.00
Good Better Best Never Let it Rest - Chicago Bears Premium Oversized Hoodie
Primotees
$63.25
University of Chicago Premium Oversized Hoodie
Ellery Lapin
$83.38
The Big Lake Gichi Gami Premium Oversized Sweatshirt
twHistory
$62.00
CHICAGO P.D - DETECTIVE JAY HALSTEAD - INTELLIGENCE BADGE VEST Pullover Hoodie
emilybraz7
$54.59
Reader Logo Through the Years Premium Oversized Hoodie
The Chicago Reader
$69.00
Coach Ben Johnson Good, Better, Best Win Speech Art Pullover Hoodie
Bear Creative
$44.84
Fire, Med, PD skyline white Premium Oversized Hoodie
ellclark
$71.88
Chicago Park District (back) Lightweight Hoodie
adrien2297
$41.99
Chicago Baseball - Lakefront Nights Premium Oversized Sweatshirt
MASMUS27
$55.29
Chicago Flag Typography – Vintage City Pride Design Premium Oversized Hoodie
SimplyJasper
$70.73
Oasis Soldier Chicago '25 Lightweight Hoodie
TraceTheFace
$44.09
University of Chicago Premium Oversized Sweatshirt
carolinezhao
$62.00
Chicago Minimalist Map United States Premium Oversized Sweatshirt
BoringClothes
$56.84
Connor Bedard Draft Art Premium Oversized Sweatshirt
B3 Graphics
$57.87
Chicago Windy City Pattern Premium Oversized Hoodie
TinyWeird
$69.00
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
End of Beginning Premium Oversized Sweatshirt
djokeerydaily
$62.00
Filipino School of Chicago Premium Oversized Sweatshirt
Fil-School-Chi
$62.00
chicago fire cast-members Premium Oversized Sweatshirt
LondownDesign
$67.17
Columbia College Chicago Flag Logo Premium Oversized Hoodie
hanhorton
$69.00
Original Chicagoland Beef Company Premium Oversized Hoodie
MalmoDesigns
$80.50
UIC College of Medicine Premium Oversized Hoodie
Nicole Christine
$77.63
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 Sweatshirt
kwald12
$59.42
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 Sweatshirt
AnsykD
$69.75
Joffrey Ballet Sign Chicago Premium Oversized Sweatshirt
Enzwell
$62.00
Chicago Football Heartbeat Pulse Premium Oversized Sweatshirt
Bored Imagination
$56.84
SIX The Musical Queens Silhouettes— With Lyrics! Pullover Sweatshirt
broadway-babies
$41.94
Chicago - The Musical/Movie Premium Oversized Sweatshirt
thefilmmagazine
$62.52
Chicago Bears Good Better Best by Coach Johnson on Colour Background Premium Oversized Sweatshirt
Bear Creative
$56.84
Bears Vintage Football Chicago Football Pullover Sweatshirt
be-njo
$43.69
CHICAGO MED - WILL HALSTEAD - SCRUBS - EMERGENCY MEDICINE Premium Oversized Hoodie
emilybraz7
$80.50
Chicago Fire Premium Oversized Sweatshirt
lemonlimeyogurt
$60.97
CHICAGO P.D - SERGEANT HANK VOIGHT - INTELLIGENCE BADGE VEST Premium Oversized Hoodie
emilybraz7
$80.50
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
Sweet Home Chicago Design Lightweight Sweatshirt
aligchi
$46.57
Vintage Wrigley Bleachers Premium Oversized Sweatshirt
frittata
$64.59
Chicago The Windy City Minimalist Art Design Premium Oversized Hoodie
BoringClothes
$63.25
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 Hoodie
Katie Thomsen
$78.78
Joffrey Ballet Sign Night Premium Oversized Sweatshirt
Enzwell
$62.00
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
CHICAGO P.D - DETECTIVE HAILEY UPTON - INTELLIGENCE BADGE VEST Pullover Sweatshirt
emilybraz7
$48.94
Fuck Fame Chicago Pullover Hoodie
TheLaw61
$47.96
808 Pullover Sweatshirt
trev4000
$47.18
Barnaby's Family Inn Premium Oversized Sweatshirt
nwerlandson
$62.00
Da Beers Premium Oversized Hoodie
Greg Dressel
$69.00
CHICAGO MED LOGO Premium Oversized Hoodie
emilybraz7
$80.50
Filipino School of Chicago White Logo Premium Oversized Hoodie
Fil-School-Chi
$69.00
Chicago PD Fire Med Premium Oversized Sweatshirt
HumorStyle
$69.75
Chicago Cloud Gate Travel Art Illustration Premium Oversized Hoodie
BoringClothes
$63.25
Portillos Premium Oversized Sweatshirt
samanthaspratt
$62.00
mt joy - hippi van bus Premium Oversized Hoodie
LondownDesign
$74.75
Chicago For Fans Premium Oversized Hoodie
CarKeeling
$69.00
Columbia College Chicago Premium Oversized Sweatshirt
hanhorton
$62.00
Joe Cool Snoopy Chicago Bears Pullover Sweatshirt
kittyr1na
$41.94
PORTILLOS Premium Oversized Sweatshirt
Fridruiz19
$64.59
Good Better Best Chicago Bears Premium Oversized Hoodie
Miarsabhoul
$76.48
Delicious Chicago Pizza Premium Oversized Sweatshirt
harebrained
$64.59
Chess Records Premium Oversized Hoodie
Retrorockit
$69.00
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Clothing
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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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