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Chicago Sweatshirts & Hoodies
1000+ items
Sweatshirts & H...
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1000+ items
Most Relevant
Vintage-Styled Bears Premium Oversized Hoodie
Daybreak Media
$69.00
Da Beers Premium Oversized Hoodie
Greg Dressel
$69.00
Joe Cool Snoopy Chicago Bears Premium Oversized Hoodie
kittyr1na
$63.25
School of the Art Institute of Chicago (SAIC) Premium Oversized Hoodie
HayleeC34
$63.25
Marshall Field's Department Store Premium Oversized Hoodie
TeeArcade84
$71.88
Air jordan Pullover Hoodie
ChristineHuth
$46.79
Chicago Minimalist Map United States Premium Oversized Hoodie
BoringClothes
$63.25
Pope Chicago White Sox - Pope Leo Xiv Premium Oversized Hoodie
BvgBytez
$69.00
I Survived The Polar Vortex - Funny Chicago Winter Humor Premium Oversized Hoodie
aligchi
$69.58
University of Chicago Law School Premium Oversized Hoodie
eammmmmm
$86.25
mt joy - hippi van bus Premium Oversized Hoodie
LondownDesign
$74.75
Chicago Black Hawk Premium Oversized Hoodie
ZamboniZingers
$69.00
School of the Art Institute of Chicago tshirt Premium Oversized Sweatshirt
stuffbysydney
$62.00
Blink if you hate the Packers Premium Oversized Sweatshirt
Primotees
$56.84
Snoopy Chicago Bears Premium Oversized Hoodie
kittyr1na
$63.25
Chicago Bears Coach Ben Johnson Full Colour Logo Premium Oversized Sweatshirt
Bear Creative
$59.42
Filipino School of Chicago White Logo Premium Oversized Sweatshirt
Fil-School-Chi
$62.00
CHICAGO P.D - DETECTIVE JAY HALSTEAD - INTELLIGENCE BADGE VEST Pullover Hoodie
emilybraz7
$54.59
Luther Burden III Choke Premium Oversized Hoodie
RatTrapTees
$63.25
Chicago Warehouse Print Premium Oversized Hoodie
Letsgodisco
$80.50
Luther Burden III vs Packers Premium Oversized Sweatshirt
Hoops and Movie Sticks
$56.84
1957 Chevy Bel Air Vintage Retro Classic Car Street Hot Rod Antique Route 66 Design Premium Oversized Hoodie
AGED Limited
$69.00
Indiana Bears Premium Oversized Sweatshirt
Primotees
$56.84
Matt Casey - lol, you're not Matt Casey - Chicago Fire Premium Oversized Hoodie
AaPink
$74.75
Art by Shepard Fairey, Shepard Fairey Art urbain Zipped Hoodie
Bob-Studio
$50.16
Chicago Blues Premium Oversized Sweatshirt
samhi113
$61.90
Patrick Kane Premium Oversized Sweatshirt
Ravenh3art
$62.00
Chicago Sox Awesome Premium Oversized Sweatshirt
FLUFFandBEYOND
$56.84
Cloud Gate Chicago Wall Art – Illinois Fall Cityscape Premium Oversized Hoodie
POSTERIOCREW
$63.25
University of Chicago Premium Oversized Hoodie
Ellery Lapin
$83.38
Reader Logo Through the Years Premium Oversized Hoodie
The Chicago Reader
$69.00
Coach Ben Johnson Good, Better, Best Win Speech Art Pullover Sweatshirt
Bear Creative
$40.19
Fire, Med, PD skyline white Premium Oversized Sweatshirt
ellclark
$64.59
Chicago Police K9 Premium Oversized Sweatshirt
Lawrence Baird
$62.00
Chicago Park District (back) Lightweight Hoodie
adrien2297
$41.99
Oasis Soldier Chicago '25 Premium Oversized Hoodie
TraceTheFace
$72.45
Connor Bedard Draft Art Premium Oversized Hoodie
B3 Graphics
$64.40
University of Chicago Premium Oversized Hoodie
carolinezhao
$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 Hoodie
brooklevan
$71.13
The Chicago College, of Performing Arts Premium Oversized Sweatshirt
NoraroN
$62.00
Columbia College Chicago Classic Logo High Quality Print Premium Oversized Sweatshirt
blomdel
$69.75
End of Beginning Premium Oversized Sweatshirt
djokeerydaily
$62.00
Sweet Vintage Retro Chicago City Flag Bear Printa Premium Oversized Hoodie
DuneHaicna
$63.25
Columbia College Chicago Flag Logo Premium Oversized Hoodie
hanhorton
$69.00
Filipino School of Chicago Premium Oversized Sweatshirt
Fil-School-Chi
$62.00
chicago fire cast-members Premium Oversized Sweatshirt
LondownDesign
$67.17
Executive Producer Dick Wolf Premium Oversized Sweatshirt
Dennis Daniel
$62.00
Original Chicagoland Beef Company Premium Oversized Sweatshirt
MalmoDesigns
$72.34
Decatur Staleys Premium Oversized Sweatshirt
Retrorockit
$62.00
Chicago Blackhawks Cross Stitch Premium Oversized Hoodie
ZamboniZingers
$69.00
UIC College of Medicine Premium Oversized Sweatshirt
Nicole Christine
$69.75
Sweet Home Chicago Design Premium Oversized Sweatshirt
aligchi
$62.52
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
Loyola CTA Stop Premium Oversized Hoodie
vellikhor
$69.00
Drose Day 1.4.25 Premium Oversized Sweatshirt
mysports
$67.17
Chicago Med tv show characters poster logo Premium Oversized Sweatshirt
AnsykD
$69.75
Chicago Football Heartbeat Pulse Premium Oversized Sweatshirt
Bored Imagination
$56.84
Vintage Chicago Skyline Illinois Adventure Premium Oversized Hoodie
T-Motive
$61.53
Joffrey Ballet Sign Chicago Premium Oversized Sweatshirt
Enzwell
$62.00
SIX The Musical Queens Silhouettes— With Lyrics! Pullover Sweatshirt
broadway-babies
$41.94
Chicago - The Musical/Movie Premium Oversized Hoodie
thefilmmagazine
$69.58
Chicago Trains Map Premium Oversized Sweatshirt
Rich Anderson
$62.00
Chicago Bears Good Better Best by Coach Johnson on Colour Background Premium Oversized Hoodie
Bear Creative
$63.25
Kanye West Dropout Bear Chicago Vintage Graduation Premium Oversized Sweatshirt
shopvinhcong
$72.34
CHICAGO P.D - SERGEANT HANK VOIGHT - INTELLIGENCE BADGE VEST Premium Oversized Hoodie
emilybraz7
$80.50
Chicago Fire Premium Oversized Sweatshirt
lemonlimeyogurt
$60.97
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
Good Better Best Never Let it Rest - Chicago Bears Premium Oversized Hoodie
Primotees
$63.25
House Music - Vintage Retro Hexagon Premium Oversized Sweatshirt
Jam Jar
$68.72
Vintage Wrigley Bleachers Premium Oversized Hoodie
frittata
$71.88
CHICAGO MED - WILL HALSTEAD - SCRUBS - EMERGENCY MEDICINE Premium Oversized Hoodie
emilybraz7
$80.50
Chicago Park District Lightweight Hoodie
adrien2297
$41.99
SAIC School of the Art Institute Chicago Van Gogh Sunflowers Premium Oversized Sweatshirt
Katie Thomsen
$70.79
Fuck Fame Chicago Pullover Hoodie
TheLaw61
$47.96
Joffrey Ballet Sign Night Premium Oversized Sweatshirt
Enzwell
$62.00
Chicago Premium Oversized Sweatshirt
JonysCreativeDesigns
$62.00
Chicago Flag Typography – Vintage City Pride Design Premium Oversized Hoodie
SimplyJasper
$70.73
Chicago Fire - One Chicago Premium Oversized Hoodie
HumorStyle
$77.63
Harrison CTA Stop Premium Oversized Hoodie
vellikhor
$69.00
CHICAGO FIRE - LT. SEVERIDE - SQUAD 3 Premium Oversized Sweatshirt
emilybraz7
$72.34
808 Premium Oversized Hoodie
trev4000
$77.63
CHICAGO P.D - DETECTIVE HAILEY UPTON - INTELLIGENCE BADGE VEST Premium Oversized Sweatshirt
emilybraz7
$72.34
Barnaby's Family Inn Premium Oversized Hoodie
nwerlandson
$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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