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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
$41.40
$69.00
(40% off)
Kanye West Dropout Bear Chicago Vintage Graduation Premium Oversized Sweatshirt
shopvinhcong
$43.40
$72.34
(40% off)
Chicago Flag Typography – Vintage City Pride Design Premium Oversized Sweatshirt
SimplyJasper
$38.13
$63.55
(40% off)
Chicago Blues Premium Oversized Sweatshirt
samhi113
$37.14
$61.90
(40% off)
Decatur Staleys Premium Oversized Sweatshirt
Retrorockit
$37.20
$62.00
(40% off)
Good Better Best Never Let it Rest - Chicago Bears Premium Oversized Hoodie
Primotees
$37.95
$63.25
(40% off)
The Big Lake Gichi Gami Premium Oversized Sweatshirt
twHistory
$37.20
$62.00
(40% off)
Downtown Chicago City Skyline Walking Bear Silhouette Gift Premium Oversized Sweatshirt
Dressed For Duty
$37.20
$62.00
(40% off)
Da Beers Chicago Bears Lightweight Sweatshirt
brandoen
$32.33
$53.89
(40% off)
Historic Route 66 - The Mother Road - Santa Monica Premium Oversized Sweatshirt
NewNomads
$37.20
$62.00
(40% off)
Joe Cool Snoopy Chicago Bears Premium Oversized Sweatshirt
kittyr1na
$34.10
$56.84
(40% off)
Bears Vintage Football Chicago Football Pullover Sweatshirt
be-njo
$32.76
$43.69
(25% off)
Chicago Minimalist Map United States Premium Oversized Hoodie
BoringClothes
$37.95
$63.25
(40% off)
Vintage Thor Motorcycles - Chicago, Illinois, U.S.A. Premium Oversized Hoodie
QuayTradingCo
$41.40
$69.00
(40% off)
University of Chicago Premium Oversized Hoodie
Ellery Lapin
$50.03
$83.38
(40% 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
$41.40
$69.00
(40% off)
Chicago Premium Oversized Sweatshirt
JonysCreativeDesigns
$37.20
$62.00
(40% off)
Coach Ben Johnson Good, Better, Best Win Speech Art Lightweight Sweatshirt
Bear Creative
$25.40
$42.34
(40% off)
Fire, Med, PD skyline white Premium Oversized Sweatshirt
ellclark
$38.75
$64.59
(40% off)
Chicago Park District (back) Lightweight Hoodie
adrien2297
$33.59
$41.99
(20% off)
Oasis Soldier Chicago '25 Lightweight Hoodie
TraceTheFace
$35.27
$44.09
(20% off)
University of Chicago Premium Oversized Sweatshirt
carolinezhao
$37.20
$62.00
(40% off)
Connor Bedard Draft Art Premium Oversized Hoodie
B3 Graphics
$38.64
$64.40
(40% off)
Loyola University Chicago Premium Oversized Sweatshirt
brooklevan
$38.35
$63.92
(40% off)
Ragtime Musical Hi-Res Premium Oversized Hoodie
blomdel
$46.58
$77.63
(40% off)
Chicago Premium Oversized Sweatshirt
JonysCreativeDesigns
$37.20
$62.00
(40% off)
Ferris Bueller at the Art Museum Premium Oversized Hoodie
comfysockz
$39.68
$66.13
(40% off)
The Chicago College, of Performing Arts Premium Oversized Hoodie
NoraroN
$41.40
$69.00
(40% off)
End of Beginning Premium Oversized Sweatshirt
djokeerydaily
$37.20
$62.00
(40% off)
Columbia College Chicago Classic Logo High Quality Print Premium Oversized Sweatshirt
blomdel
$41.85
$69.75
(40% off)
Moody Bible Institute Premium Oversized Sweatshirt
Bloom Faithfully
$37.20
$62.00
(40% off)
Columbia College Chicago Flag Logo Premium Oversized Sweatshirt
hanhorton
$37.20
$62.00
(40% off)
Filipino School of Chicago Premium Oversized Sweatshirt
Fil-School-Chi
$37.20
$62.00
(40% off)
chicago fire cast-members Premium Oversized Sweatshirt
LondownDesign
$40.30
$67.17
(40% off)
Original Chicagoland Beef Company Premium Oversized Hoodie
MalmoDesigns
$48.30
$80.50
(40% off)
UIC College of Medicine Premium Oversized Sweatshirt
Nicole Christine
$41.85
$69.75
(40% off)
Chicago FC United logo usl Premium Oversized Sweatshirt
chcasey
$37.20
$62.00
(40% off)
Chicago Flags with Teams and Skyline Premium Oversized Hoodie
kwald12
$39.68
$66.13
(40% off)
School of the Art Institute of Chicago Rainbow Gradient Logo Pullover Hoodie
Dennisust
$35.09
$46.79
(25% off)
Columbia College Chicago Premium Oversized Hoodie
blomdel
$46.58
$77.63
(40% off)
Drose Day 1.4.25 Premium Oversized Sweatshirt
mysports
$40.30
$67.17
(40% off)
Chicago Med tv show characters poster logo Premium Oversized Hoodie
AnsykD
$46.58
$77.63
(40% off)
Joffrey Ballet Sign Chicago Premium Oversized Sweatshirt
Enzwell
$37.20
$62.00
(40% off)
Chicago Football Heartbeat Pulse Premium Oversized Sweatshirt
Bored Imagination
$34.10
$56.84
(40% off)
Big Apple of Chicago Skyline Minimalist Art Premium Oversized Hoodie
BoringClothes
$37.95
$63.25
(40% off)
SIX The Musical Queens Silhouettes— With Lyrics! Pullover Sweatshirt
broadway-babies
$31.45
$41.94
(25% off)
Chicago - The Musical/Movie Premium Oversized Hoodie
thefilmmagazine
$41.75
$69.58
(40% off)
Chicago Bears Good Better Best by Coach Johnson on Colour Background Lightweight Sweatshirt
Bear Creative
$25.40
$42.34
(40% off)
Vintage Chicago 1955 Team Pride Art Premium Oversized Sweatshirt
Normandy Road Heritage™ - Vintage Garage Art
$43.40
$72.34
(40% off)
Chicago Fire Premium Oversized Sweatshirt
lemonlimeyogurt
$36.58
$60.97
(40% off)
CHICAGO MED - WILL HALSTEAD - SCRUBS - EMERGENCY MEDICINE Premium Oversized Hoodie
emilybraz7
$48.30
$80.50
(40% off)
Chicago the Musical Pullover Hoodie
Rasiadunn
$35.09
$46.79
(25% off)
CHICAGO P.D - SERGEANT HANK VOIGHT - INTELLIGENCE BADGE VEST Premium Oversized Hoodie
emilybraz7
$48.30
$80.50
(40% off)
Marshall Field's Department Store Premium Oversized Sweatshirt
TeeArcade84
$38.75
$64.59
(40% off)
School of the Art Institute of Chicago (SAIC) Pullover Sweatshirt
HayleeC34
$28.83
$38.45
(25% off)
CHICAGO FIRE CFD LOGO Premium Oversized Sweatshirt
emilybraz7
$43.40
$72.34
(40% off)
House Music - Vintage Retro Hexagon Premium Oversized Sweatshirt
Jam Jar
$41.23
$68.72
(40% off)
Vintage Wrigley Bleachers Premium Oversized Hoodie
frittata
$43.13
$71.88
(40% off)
Chicago Park District Lightweight Hoodie
adrien2297
$33.59
$41.99
(20% off)
Chicago The Windy City Minimalist Art Design Premium Oversized Sweatshirt
BoringClothes
$34.10
$56.84
(40% off)
SAIC School of the Art Institute Chicago Van Gogh Sunflowers Premium Oversized Hoodie
Katie Thomsen
$47.27
$78.78
(40% off)
Joffrey Ballet Sign Night Premium Oversized Hoodie
Enzwell
$41.40
$69.00
(40% off)
Chicago Fire - One Chicago Premium Oversized Hoodie
HumorStyle
$46.58
$77.63
(40% off)
808 Premium Oversized Sweatshirt
trev4000
$41.85
$69.75
(40% off)
CHICAGO FIRE - LT. SEVERIDE - SQUAD 3 Pullover Hoodie
emilybraz7
$40.93
$54.59
(25% off)
Alex Caruso Mirror GOAT (Chicago) Pullover Hoodie
RatTrapTees
$38.01
$50.69
(25% off)
CHICAGO P.D - DETECTIVE HAILEY UPTON - INTELLIGENCE BADGE VEST Premium Oversized Sweatshirt
emilybraz7
$43.40
$72.34
(40% off)
Fuck Fame Chicago Pullover Hoodie
TheLaw61
$35.97
$47.96
(25% off)
Barnaby's Family Inn Premium Oversized Hoodie
nwerlandson
$41.40
$69.00
(40% off)
Da Beers Premium Oversized Sweatshirt
Greg Dressel
$37.20
$62.00
(40% off)
CHICAGO MED LOGO Premium Oversized Hoodie
emilybraz7
$48.30
$80.50
(40% off)
Filipino School of Chicago White Logo Premium Oversized Hoodie
Fil-School-Chi
$41.40
$69.00
(40% off)
Chicago PD Fire Med Premium Oversized Sweatshirt
HumorStyle
$41.85
$69.75
(40% off)
Chicago Elevated Train Typography | The Loop City Skyline Art Premium Oversized Sweatshirt
SimplyJasper
$38.13
$63.55
(40% off)
Portillos Premium Oversized Hoodie
samanthaspratt
$41.40
$69.00
(40% off)
mt joy - hippi van bus Premium Oversized Hoodie
LondownDesign
$44.85
$74.75
(40% off)
Chicago Trains Map Premium Oversized Sweatshirt
Rich Anderson
$37.20
$62.00
(40% off)
Chicago For Fans Premium Oversized Hoodie
CarKeeling
$41.40
$69.00
(40% off)
Columbia College Chicago Premium Oversized Sweatshirt
hanhorton
$37.20
$62.00
(40% off)
PORTILLOS Premium Oversized Hoodie
Fridruiz19
$43.13
$71.88
(40% off)
Good Better Best Chicago Bears Premium Oversized Hoodie
Miarsabhoul
$45.89
$76.48
(40% off)
Polka will never Die Riding A Rex Harry Random Destruction Dresden Premium Oversized Hoodie
idwearit
$41.40
$69.00
(40% off)
Pope Chicago White Sox - Pope Leo Xiv Premium Oversized Hoodie
BvgBytez
$41.40
$69.00
(40% off)
Delicious Chicago Pizza Premium Oversized Sweatshirt
harebrained
$38.75
$64.59
(40% off)
And all that jazz, chicago the musical Premium Oversized Sweatshirt
PoppysMTPrints
$38.75
$64.59
(40% off)
Chess Records Premium Oversized Sweatshirt
Retrorockit
$37.20
$62.00
(40% off)
Vintage Columbia College Chicago Illinois Premium Oversized Hoodie
BackinDaysUni
$44.85
$74.75
(40% off)
Marshall Field's Department Store Premium Oversized Sweatshirt
TeeArcade84
$38.75
$64.59
(40% off)
Philadelphia International Records Premium Oversized Sweatshirt
goatboyjr
$37.20
$62.00
(40% off)
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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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