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Chicago Sweatshirts & Hoodies
1000+ items
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1000+ items
Most Relevant
Vintage-Styled Bears Premium Oversized Hoodie
Daybreak Media
$51.76
$69.00
(25% off)
Bears Vintage Football Chicago Football Pullover Sweatshirt
be-njo
$32.76
$43.69
(25% off)
End of Beginning Premium Oversized Sweatshirt
djokeerydaily
$49.61
$62.00
(20% off)
Fire department - Rescue team - Chicago Illinois Pullover Sweatshirt
Random Tees
$32.76
$43.69
(25% off)
Moody Bible Institute Premium Oversized Hoodie
Bloom Faithfully
$51.76
$69.00
(25% off)
Chicago Bear Pullover Sweatshirt
motivato
$31.19
$41.59
(25% off)
Chicago the Musical Premium Oversized Sweatshirt
Top-show-shirts
$51.67
$64.59
(20% off)
Pope Chicago White Sox - Pope Leo Xiv Premium Oversized Hoodie
BvgBytez
$51.76
$69.00
(25% off)
CHICAGO-CUBS-RETRO-2-BY-BUCK-TEE-T-SHIRT Lightweight Sweatshirt
RobynBrownA
$34.64
$46.19
(25% off)
Muddy Waters vs. Howlin' Wolf - Club Paradise 1964 Premium Oversized Sweatshirt
Primotees
$45.47
$56.84
(20% off)
House Music - Chicago 1985 Premium Oversized Hoodie
perkinskristie
$62.11
$82.80
(25% off)
University of Chicago Premium Oversized Hoodie
Ellery Lapin
$62.54
$83.38
(25% off)
CHICAGO P.D - DETECTIVE JAY HALSTEAD - INTELLIGENCE BADGE VEST Pullover Hoodie
emilybraz7
$40.93
$54.59
(25% off)
Reader Logo Through the Years Premium Oversized Hoodie
The Chicago Reader
$51.76
$69.00
(25% off)
Coach Ben Johnson Good, Better, Best Win Speech Art Lightweight Sweatshirt
Bear Creative
$31.76
$42.34
(25% off)
Fire, Med, PD skyline white Premium Oversized Hoodie
ellclark
$53.91
$71.88
(25% off)
Chicago Flag Typography – Vintage City Pride Design Premium Oversized Sweatshirt
SimplyJasper
$50.85
$63.55
(20% off)
Chicago Park District (back) Lightweight Hoodie
adrien2297
$33.59
$41.99
(20% off)
I grew up in Chicago you gotta problem with that?! Premium Oversized Hoodie
123ks
$60.38
$80.50
(25% off)
Oasis Soldier Chicago '25 Lightweight Hoodie
TraceTheFace
$35.27
$44.09
(20% off)
University of Chicago Premium Oversized Sweatshirt
carolinezhao
$49.61
$62.00
(20% off)
Connor Bedard Draft Art Premium Oversized Sweatshirt
B3 Graphics
$46.30
$57.87
(20% off)
Ragtime Musical Hi-Res Premium Oversized Hoodie
blomdel
$58.22
$77.63
(25% off)
Chicago Premium Oversized Sweatshirt
JonysCreativeDesigns
$49.61
$62.00
(20% off)
Ferris Bueller at the Art Museum Premium Oversized Hoodie
comfysockz
$49.60
$66.13
(25% off)
Loyola University Chicago Premium Oversized Sweatshirt
brooklevan
$51.14
$63.92
(20% off)
The Chicago College, of Performing Arts Premium Oversized Hoodie
NoraroN
$51.76
$69.00
(25% off)
Columbia College Chicago Classic Logo High Quality Print Premium Oversized Hoodie
blomdel
$58.22
$77.63
(25% off)
Filipino School of Chicago Zipped Hoodie
Fil-School-Chi
$34.39
$43.00
(20% off)
Columbia College Chicago Flag Logo Premium Oversized Hoodie
hanhorton
$51.76
$69.00
(25% off)
Chicago Blues Premium Oversized Sweatshirt
samhi113
$49.52
$61.90
(20% off)
chicago fire cast-members Premium Oversized Sweatshirt
LondownDesign
$53.74
$67.17
(20% off)
Original Chicagoland Beef Company Premium Oversized Hoodie
MalmoDesigns
$60.38
$80.50
(25% off)
UIC College of Medicine Premium Oversized Hoodie
Nicole Christine
$58.22
$77.63
(25% off)
Chicago FC United logo usl Premium Oversized Sweatshirt
chcasey
$49.61
$62.00
(20% off)
School of the Art Institute of Chicago Rainbow Gradient Logo Pullover Hoodie
Dennisust
$35.09
$46.79
(25% off)
Chicago Flags with Teams and Skyline Premium Oversized Sweatshirt
kwald12
$47.54
$59.42
(20% off)
Columbia College Chicago Premium Oversized Hoodie
blomdel
$58.22
$77.63
(25% off)
Drose Day 1.4.25 Premium Oversized Sweatshirt
mysports
$53.74
$67.17
(20% off)
Chicago Med tv show characters poster logo Premium Oversized Hoodie
AnsykD
$58.22
$77.63
(25% off)
Chicago Cloud Gate Travel Art Illustration Premium Oversized Hoodie
BoringClothes
$47.44
$63.25
(25% off)
Joffrey Ballet Sign Chicago Premium Oversized Sweatshirt
Enzwell
$49.61
$62.00
(20% off)
Chicago Football Heartbeat Pulse Premium Oversized Hoodie
Bored Imagination
$47.44
$63.25
(25% off)
Decatur Staleys Premium Oversized Sweatshirt
Retrorockit
$49.61
$62.00
(20% off)
SIX The Musical Queens Silhouettes— With Lyrics! Pullover Sweatshirt
broadway-babies
$31.45
$41.94
(25% off)
Chicago - The Musical/Movie Premium Oversized Sweatshirt
thefilmmagazine
$50.02
$62.52
(20% off)
Chicago Bears Good Better Best by Coach Johnson on Colour Background Premium Oversized Hoodie
Bear Creative
$47.44
$63.25
(25% off)
CHICAGO MED - WILL HALSTEAD - SCRUBS - EMERGENCY MEDICINE Premium Oversized Hoodie
emilybraz7
$60.38
$80.50
(25% off)
CHICAGO P.D - SERGEANT HANK VOIGHT - INTELLIGENCE BADGE VEST Premium Oversized Sweatshirt
emilybraz7
$57.87
$72.34
(20% off)
Chicago Fire Premium Oversized Sweatshirt
lemonlimeyogurt
$48.78
$60.97
(20% off)
Chicago the Musical Pullover Hoodie
Rasiadunn
$35.09
$46.79
(25% off)
Marshall Field's Department Store Premium Oversized Sweatshirt
TeeArcade84
$51.67
$64.59
(20% off)
CHICAGO FIRE CFD LOGO Premium Oversized Sweatshirt
emilybraz7
$57.87
$72.34
(20% off)
School of the Art Institute of Chicago (SAIC) Premium Oversized Hoodie
HayleeC34
$47.44
$63.25
(25% off)
House Music - Vintage Retro Hexagon Premium Oversized Sweatshirt
Jam Jar
$54.98
$68.72
(20% off)
Vintage Wrigley Bleachers Premium Oversized Hoodie
frittata
$53.91
$71.88
(25% off)
Chicago Park District Lightweight Hoodie
adrien2297
$33.59
$41.99
(20% off)
Joffrey Ballet Sign Night Premium Oversized Hoodie
Enzwell
$51.76
$69.00
(25% off)
SAIC School of the Art Institute Chicago Van Gogh Sunflowers Premium Oversized Sweatshirt
Katie Thomsen
$56.63
$70.79
(20% off)
808 Premium Oversized Hoodie
trev4000
$58.22
$77.63
(25% off)
Big Apple of Chicago Skyline Minimalist Art Premium Oversized Sweatshirt
BoringClothes
$45.47
$56.84
(20% off)
Chicago Fire - One Chicago Premium Oversized Hoodie
HumorStyle
$58.22
$77.63
(25% off)
CHICAGO FIRE - LT. SEVERIDE - SQUAD 3 Premium Oversized Hoodie
emilybraz7
$60.38
$80.50
(25% off)
Alex Caruso Mirror GOAT (Chicago) Premium Oversized Sweatshirt
RatTrapTees
$53.74
$67.17
(20% off)
Fuck Fame Chicago Pullover Hoodie
TheLaw61
$35.97
$47.96
(25% off)
CHICAGO P.D - DETECTIVE HAILEY UPTON - INTELLIGENCE BADGE VEST Premium Oversized Hoodie
emilybraz7
$60.38
$80.50
(25% off)
Chicago Police Department Patch Premium Oversized Hoodie
LockedUp
$63.83
$85.10
(25% off)
Chicago Premium Oversized Hoodie
JonysCreativeDesigns
$56.07
$74.75
(25% off)
Barnaby's Family Inn Premium Oversized Sweatshirt
nwerlandson
$49.61
$62.00
(20% off)
Da Beers Premium Oversized Hoodie
Greg Dressel
$51.76
$69.00
(25% off)
CHICAGO MED LOGO Premium Oversized Sweatshirt
emilybraz7
$57.87
$72.34
(20% off)
Filipino School of Chicago White Logo Premium Oversized Hoodie
Fil-School-Chi
$51.76
$69.00
(25% off)
Chicago PD Fire Med Premium Oversized Hoodie
HumorStyle
$58.22
$77.63
(25% off)
Portillos Premium Oversized Sweatshirt
samanthaspratt
$49.61
$62.00
(20% off)
Good Better Best Never Let it Rest - Chicago Bears Premium Oversized Sweatshirt
Primotees
$45.47
$56.84
(20% off)
mt joy - hippi van bus Premium Oversized Sweatshirt
LondownDesign
$53.74
$67.17
(20% off)
Chicago For Fans Premium Oversized Sweatshirt
CarKeeling
$49.61
$62.00
(20% off)
Chicago Trains Map Premium Oversized Hoodie
Rich Anderson
$51.76
$69.00
(25% off)
Columbia College Chicago Premium Oversized Sweatshirt
hanhorton
$49.61
$62.00
(20% off)
PORTILLOS Premium Oversized Hoodie
Fridruiz19
$53.91
$71.88
(25% off)
Good Better Best Chicago Bears Premium Oversized Hoodie
Miarsabhoul
$57.36
$76.48
(25% off)
Bear Down Premium Oversized Sweatshirt
Primotees
$45.47
$56.84
(20% off)
Delicious Chicago Pizza Premium Oversized Sweatshirt
harebrained
$51.67
$64.59
(20% off)
Polka will never Die Riding A Rex Harry Random Destruction Dresden Premium Oversized Hoodie
idwearit
$51.76
$69.00
(25% off)
Vintage Columbia College Chicago Illinois Premium Oversized Hoodie
BackinDaysUni
$56.07
$74.75
(25% off)
And all that jazz, chicago the musical Premium Oversized Sweatshirt
PoppysMTPrints
$51.67
$64.59
(20% off)
Chicago Elevated Train Typography | The Loop City Skyline Art Premium Oversized Sweatshirt
SimplyJasper
$50.85
$63.55
(20% off)
Chicago The Windy City Minimalist Art Design Premium Oversized Hoodie
BoringClothes
$47.44
$63.25
(25% off)
Marshall Field's Department Store Premium Oversized Hoodie
TeeArcade84
$53.91
$71.88
(25% off)
Philadelphia International Records Premium Oversized Hoodie
goatboyjr
$51.76
$69.00
(25% off)
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Clothing
Sweatshirt
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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