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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
$41.40
$69.00
(40% off)
Chicago Trains Map Premium Oversized Hoodie
Rich Anderson
$41.40
$69.00
(40% off)
Luther Burden III Choke Premium Oversized Sweatshirt
RatTrapTees
$39.79
$56.84
(30% off)
Executive Producer Dick Wolf Premium Oversized Sweatshirt
Dennis Daniel
$43.40
$62.00
(30% off)
Chicago Blues Premium Oversized Sweatshirt
samhi113
$43.33
$61.90
(30% off)
Kanye West Dropout Bear Chicago Vintage Graduation Premium Oversized Sweatshirt
shopvinhcong
$50.64
$72.34
(30% off)
Vintage Chicago Skyline Illinois Adventure Premium Oversized Sweatshirt
T-Motive
$39.79
$56.84
(30% off)
Dennis Rodmans Green Hair Worm Premium Oversized Sweatshirt
AbbelSwords
$43.40
$62.00
(30% off)
Wizard Beer Pullover Sweatshirt
fanartdesigns
$32.76
$43.69
(25% off)
c bears of the king team Premium Oversized Hoodie
jerrybecker1
$41.40
$69.00
(40% off)
Chicago CTA Sign Premium Oversized Sweatshirt
vellikhor
$43.40
$62.00
(30% off)
Chicago Black Hawk Premium Oversized Hoodie
ZamboniZingers
$41.40
$69.00
(40% off)
Chicago Pride School Bus Gossip Premium Oversized Hoodie
New Wave Artworks & Odds &Ends
$37.95
$63.25
(40% off)
Chicago Blackhawks Cross Stitch Premium Oversized Hoodie
ZamboniZingers
$41.40
$69.00
(40% off)
Chicago Hockey Premium Oversized Hoodie
sashka1998
$40.37
$67.28
(40% off)
Wilson to 95/Dan Ryan Premium Oversized Sweatshirt
annaoze
$43.40
$62.00
(30% off)
BTS World Tour 2026 Arirang. CHICAGO. Premium Oversized Sweatshirt
EunsooLee
$43.40
$62.00
(30% off)
Save Ferris Badge Premium Oversized Hoodie
Indestructibbo
$43.13
$71.88
(40% off)
Goose Retro (Station Wagon) Premium Oversized Sweatshirt
in-verona
$43.40
$62.00
(30% off)
Sweet Home Chicago Design Premium Oversized Hoodie
aligchi
$41.75
$69.58
(40% off)
Juice wrld vector art Premium Oversized Sweatshirt
Rusdiii
$43.40
$62.00
(30% off)
Viagra Boys Premium Oversized Hoodie
marwanerrady
$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)
Coach Ben Johnson Good, Better, Best Win Speech Art Zipped Hoodie
Bear Creative
$34.80
$43.49
(20% off)
Fire, Med, PD skyline white Premium Oversized Hoodie
ellclark
$43.13
$71.88
(40% off)
Chicago Park District (back) Lightweight Hoodie
adrien2297
$33.59
$41.99
(20% off)
Downtown Chicago City Skyline Walking Bear Silhouette Gift Premium Oversized Sweatshirt
Dressed For Duty
$43.40
$62.00
(30% off)
Oasis Soldier Chicago '25 Premium Oversized Hoodie
TraceTheFace
$43.47
$72.45
(40% off)
Chicago Built by the Lake - Baseball City Lightweight Sweatshirt
MASMUS27
$30.89
$41.18
(25% off)
University of Chicago Premium Oversized Sweatshirt
carolinezhao
$43.40
$62.00
(30% off)
Connor Bedard Draft Art Premium Oversized Hoodie
B3 Graphics
$38.64
$64.40
(40% off)
Loyola University Chicago Premium Oversized Hoodie
brooklevan
$42.68
$71.13
(40% off)
Decatur Staleys Premium Oversized Hoodie
Retrorockit
$41.40
$69.00
(40% off)
Ragtime Musical Hi-Res Premium Oversized Hoodie
blomdel
$46.58
$77.63
(40% off)
Chicago Windy City Pattern Premium Oversized Hoodie
TinyWeird
$41.40
$69.00
(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
$43.40
$62.00
(30% off)
Columbia College Chicago Classic Logo High Quality Print Premium Oversized Hoodie
blomdel
$46.58
$77.63
(40% off)
Columbia College Chicago Flag Logo Premium Oversized Hoodie
hanhorton
$41.40
$69.00
(40% off)
Filipino School of Chicago Premium Oversized Hoodie
Fil-School-Chi
$41.40
$69.00
(40% off)
chicago fire cast-members Premium Oversized Sweatshirt
LondownDesign
$47.02
$67.17
(30% off)
Original Chicagoland Beef Company Premium Oversized Sweatshirt
MalmoDesigns
$50.64
$72.34
(30% off)
UIC College of Medicine Premium Oversized Sweatshirt
Nicole Christine
$48.83
$69.75
(30% off)
Chicago FC United logo usl Premium Oversized Sweatshirt
chcasey
$43.40
$62.00
(30% 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
$41.60
$59.42
(30% off)
Columbia College Chicago Premium Oversized Sweatshirt
blomdel
$48.83
$69.75
(30% off)
Drose Day 1.4.25 Premium Oversized Sweatshirt
mysports
$47.02
$67.17
(30% off)
Chicago Med tv show characters poster logo Premium Oversized Hoodie
AnsykD
$46.58
$77.63
(40% off)
Chicago Minimalist Map United States Premium Oversized Sweatshirt
BoringClothes
$39.79
$56.84
(30% off)
Chicago Football Heartbeat Pulse Premium Oversized Hoodie
Bored Imagination
$37.95
$63.25
(40% off)
Joffrey Ballet Sign Chicago Premium Oversized Sweatshirt
Enzwell
$43.40
$62.00
(30% 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)
Good Better Best Never Let it Rest - Chicago Bears Premium Oversized Hoodie
Primotees
$37.95
$63.25
(40% off)
Chicago Bears Good Better Best by Coach Johnson on Colour Background Premium Oversized Sweatshirt
Bear Creative
$39.79
$56.84
(30% off)
Chicago Fire Premium Oversized Sweatshirt
lemonlimeyogurt
$42.68
$60.97
(30% off)
CHICAGO MED - WILL HALSTEAD - SCRUBS - EMERGENCY MEDICINE Premium Oversized Hoodie
emilybraz7
$48.30
$80.50
(40% off)
CHICAGO P.D - SERGEANT HANK VOIGHT - INTELLIGENCE BADGE VEST Premium Oversized Hoodie
emilybraz7
$48.30
$80.50
(40% off)
Chicago the Musical Pullover Hoodie
Rasiadunn
$35.09
$46.79
(25% off)
CHICAGO FIRE CFD LOGO Premium Oversized Sweatshirt
emilybraz7
$50.64
$72.34
(30% off)
Marshall Field's Department Store Premium Oversized Sweatshirt
TeeArcade84
$45.21
$64.59
(30% off)
Chicago Police Department Patch Premium Oversized Hoodie
LockedUp
$51.06
$85.10
(40% off)
House Music - Vintage Retro Hexagon Premium Oversized Sweatshirt
Jam Jar
$48.11
$68.72
(30% 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)
School of the Art Institute of Chicago (SAIC) Premium Oversized Hoodie
HayleeC34
$37.95
$63.25
(40% off)
SAIC School of the Art Institute Chicago Van Gogh Sunflowers Pullover Sweatshirt
Katie Thomsen
$35.91
$47.88
(25% off)
Joffrey Ballet Sign Night Premium Oversized Hoodie
Enzwell
$41.40
$69.00
(40% off)
CHICAGO FIRE - LT. SEVERIDE - SQUAD 3 Premium Oversized Sweatshirt
emilybraz7
$50.64
$72.34
(30% off)
Alex Caruso Mirror GOAT (Chicago) Premium Oversized Sweatshirt
RatTrapTees
$47.02
$67.17
(30% off)
Chicago Fire - One Chicago Premium Oversized Hoodie
HumorStyle
$46.58
$77.63
(40% off)
808 Premium Oversized Hoodie
trev4000
$46.58
$77.63
(40% off)
Fuck Fame Chicago Pullover Hoodie
TheLaw61
$35.97
$47.96
(25% off)
Chicago Premium Oversized Hoodie
JonysCreativeDesigns
$44.85
$74.75
(40% off)
CHICAGO P.D - DETECTIVE HAILEY UPTON - INTELLIGENCE BADGE VEST Premium Oversized Sweatshirt
emilybraz7
$50.64
$72.34
(30% off)
Barnaby's Family Inn Premium Oversized Sweatshirt
nwerlandson
$43.40
$62.00
(30% off)
Da Beers Premium Oversized Sweatshirt
Greg Dressel
$43.40
$62.00
(30% off)
Filipino School of Chicago White Logo Premium Oversized Sweatshirt
Fil-School-Chi
$43.40
$62.00
(30% off)
CHICAGO MED LOGO Premium Oversized Hoodie
emilybraz7
$48.30
$80.50
(40% off)
Chicago PD Fire Med Premium Oversized Sweatshirt
HumorStyle
$48.83
$69.75
(30% off)
Chicago Flag Typography – Vintage City Pride Design Premium Oversized Hoodie
SimplyJasper
$42.44
$70.73
(40% off)
Portillos Premium Oversized Sweatshirt
samanthaspratt
$43.40
$62.00
(30% off)
mt joy - hippi van bus Premium Oversized Hoodie
LondownDesign
$44.85
$74.75
(40% off)
Chicago For Fans Premium Oversized Sweatshirt
CarKeeling
$43.40
$62.00
(30% off)
PORTILLOS Premium Oversized Hoodie
Fridruiz19
$43.13
$71.88
(40% off)
Good Better Best Chicago Bears Pullover Hoodie
Miarsabhoul
$38.89
$51.86
(25% off)
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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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