Chicago Sweatshirts & Hoodies

1000+ items

Vintage-Styled Bears Premium Oversized Hoodie

Daybreak Media

$51.76

~~$69.00~~ (25% off)

Bear Down Premium Oversized Hoodie

Primotees

$47.44

~~$63.25~~ (25% off)

The Bear - The Original Berf of Chicagoland Logo in White Premium Oversized Hoodie

Bear Creative

$49.60

~~$66.13~~ (25% off)

Indiana Bears Premium Oversized Sweatshirt

Primotees

$45.47

~~$56.84~~ (20% off)

Gary Bears Premium Oversized Sweatshirt

Primotees

$45.47

~~$56.84~~ (20% off)

Chicago Logo 3 Premium Oversized Hoodie

GrimaceGraphics

$51.76

~~$69.00~~ (25% off)

The Bear - The Original Beef of Chicagoland Premium Oversized Hoodie

kayability

$51.76

~~$69.00~~ (25% off)

Payton #34. Chicago Bears Pullover Hoodie

Primotees

$37.43

~~$46.79~~ (20% off)

BERNIE MAC Premium Oversized Hoodie

Portraits by Billy H. Jackson

$51.76

~~$69.00~~ (25% off)

CHICAGO FIRE LOGO Pullover Hoodie

emilybraz7

$43.67

~~$54.59~~ (20% 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

$43.67

~~$54.59~~ (20% off)

Reader Logo Through the Years Premium Oversized Sweatshirt

The Chicago Reader

$49.61

~~$62.00~~ (20% off)

Coach Ben Johnson Good, Better, Best Win Speech Art Pullover Hoodie

Bear Creative

$35.87

~~$44.84~~ (20% off)

Fire, Med, PD skyline white Premium Oversized Sweatshirt

ellclark

$51.67

~~$64.59~~ (20% off)

Chicago Park District (back) Lightweight Hoodie

adrien2297

$33.59

~~$41.99~~ (20% off)

UIC College of Medicine Premium Oversized Hoodie

Nicole Christine

$58.22

~~$77.63~~ (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)

Chicago Premium Oversized Hoodie

JonysCreativeDesigns

$56.07

~~$74.75~~ (25% off)

Ragtime Musical Hi-Res Premium Oversized Hoodie

blomdel

$58.22

~~$77.63~~ (25% off)

Loyola University Chicago Premium Oversized Hoodie

brooklevan

$53.35

~~$71.13~~ (25% off)

Ferris Bueller at the Art Museum Premium Oversized Hoodie

comfysockz

$49.60

~~$66.13~~ (25% 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)

Chicago Blues Premium Oversized Sweatshirt

samhi113

$49.52

~~$61.90~~ (20% off)

Columbia College Chicago Flag Logo Premium Oversized Sweatshirt

hanhorton

$49.61

~~$62.00~~ (20% off)

Chicago Cloud Gate Travel Art Illustration Premium Oversized Hoodie

BoringClothes

$47.44

~~$63.25~~ (25% off)

Filipino School of Chicago Premium Oversized Sweatshirt

Fil-School-Chi

$49.61

~~$62.00~~ (20% off)

chicago fire cast-members Premium Oversized Hoodie

LondownDesign

$56.07

~~$74.75~~ (25% off)

Original Chicagoland Beef Company Pullover Sweatshirt

MalmoDesigns

$39.14

~~$48.93~~ (20% off)

Chicago FC United logo usl Premium Oversized Hoodie

chcasey

$51.76

~~$69.00~~ (25% off)

Chicago Flags with Teams and Skyline Premium Oversized Hoodie

kwald12

$49.60

~~$66.13~~ (25% off)

School of the Art Institute of Chicago Rainbow Gradient Logo Pullover Hoodie

Dennisust

$37.43

~~$46.79~~ (20% off)

Columbia College Chicago Premium Oversized Hoodie

blomdel

$58.22

~~$77.63~~ (25% off)

Chicago Premium Oversized Hoodie

JonysCreativeDesigns

$56.07

~~$74.75~~ (25% off)

Chicago Med tv show characters poster logo Premium Oversized Hoodie

AnsykD

$58.22

~~$77.63~~ (25% off)

Drose Day 1.4.25 Premium Oversized Sweatshirt

mysports

$53.74

~~$67.17~~ (20% off)

Chicago Football Heartbeat Pulse Premium Oversized Sweatshirt

Bored Imagination

$49.61

~~$62.00~~ (20% off)

Joffrey Ballet Sign Chicago Premium Oversized Sweatshirt

Enzwell

$49.61

~~$62.00~~ (20% off)

Decatur Staleys Premium Oversized Hoodie

Retrorockit

$51.76

~~$69.00~~ (25% off)

Big Apple of Chicago Skyline Minimalist Art Premium Oversized Hoodie

BoringClothes

$47.44

~~$63.25~~ (25% off)

End of Beginning Premium Oversized Sweatshirt

djokeerydaily

$49.61

~~$62.00~~ (20% off)

SIX The Musical Queens Silhouettes— With Lyrics! Pullover Sweatshirt

broadway-babies

$33.55

~~$41.94~~ (20% 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 P.D - SERGEANT HANK VOIGHT - INTELLIGENCE BADGE VEST Premium Oversized Sweatshirt

emilybraz7

$57.87

~~$72.34~~ (20% off)

CHICAGO MED - WILL HALSTEAD - SCRUBS - EMERGENCY MEDICINE 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

$37.43

~~$46.79~~ (20% off)

School of the Art Institute of Chicago (SAIC) Premium Oversized Sweatshirt

HayleeC34

$45.47

~~$56.84~~ (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 Sweatshirt

TeeArcade84

$51.67

~~$64.59~~ (20% off)

CHICAGO FIRE CFD LOGO Premium Oversized Sweatshirt

emilybraz7

$57.87

~~$72.34~~ (20% off)

House Music - Vintage Retro Hexagon Premium Oversized Sweatshirt

Jam Jar

$54.98

~~$68.72~~ (20% off)

Chicago Premium Oversized Sweatshirt

JonysCreativeDesigns

$49.61

~~$62.00~~ (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)

SAIC School of the Art Institute Chicago Van Gogh Sunflowers Premium Oversized Sweatshirt

Katie Thomsen

$56.63

~~$70.79~~ (20% off)

Blue Bear with Golden Face Premium Oversized Hoodie

maulanaansyh

$51.76

~~$69.00~~ (25% off)

Joffrey Ballet Sign Night Premium Oversized Hoodie

Enzwell

$51.76

~~$69.00~~ (25% off)

Chicago Fire - One Chicago Premium Oversized Hoodie

HumorStyle

$58.22

~~$77.63~~ (25% off)

808 Premium Oversized Sweatshirt

trev4000

$55.81

~~$69.75~~ (20% 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

$38.36

~~$47.96~~ (20% off)

CHICAGO P.D - DETECTIVE HAILEY UPTON - INTELLIGENCE BADGE VEST Premium Oversized Hoodie

emilybraz7

$60.38

~~$80.50~~ (25% off)

Da Beers Premium Oversized Sweatshirt

Greg Dressel

$49.61

~~$62.00~~ (20% off)

Barnaby's Family Inn Premium Oversized Hoodie

nwerlandson

$51.76

~~$69.00~~ (25% off)

Filipino School of Chicago White Logo Premium Oversized Sweatshirt

Fil-School-Chi

$49.61

~~$62.00~~ (20% off)

CHICAGO MED LOGO Premium Oversized Sweatshirt

emilybraz7

$57.87

~~$72.34~~ (20% off)

Chicago Skyline Minimalist Blue Line Art Premium Oversized Hoodie

BoringClothes

$47.44

~~$63.25~~ (25% off)

Chicago PD Fire Med Premium Oversized Sweatshirt

HumorStyle

$55.81

~~$69.75~~ (20% off)

Portillos Premium Oversized Sweatshirt

samanthaspratt

$49.61

~~$62.00~~ (20% off)

Da Pope Malört & Savior Meme Design Premium Oversized Sweatshirt

BousinilyArt

$45.47

~~$56.84~~ (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 Trains Map Premium Oversized Hoodie

Rich Anderson

$51.76

~~$69.00~~ (25% off)

Chicago For Fans Premium Oversized Hoodie

CarKeeling

$51.76

~~$69.00~~ (25% off)

Chicago Police Department Patch Premium Oversized Sweatshirt

LockedUp

$61.18

~~$76.47~~ (20% off)

Polka will never Die Riding A Rex Harry Random Destruction Dresden Premium Oversized Hoodie

idwearit

$51.76

~~$69.00~~ (25% off)

Columbia College Chicago Pullover Hoodie

hanhorton

$37.43

~~$46.79~~ (20% off)

CHICAGO MED - NATALIE MANNING - SCRUBS - EMERGENCY MEDICINE Premium Oversized Hoodie

emilybraz7

$60.38

~~$80.50~~ (25% off)

PORTILLOS Premium Oversized Hoodie

Fridruiz19

$53.91

~~$71.88~~ (25% off)

Delicious Chicago Pizza Premium Oversized Sweatshirt

harebrained

$51.67

~~$64.59~~ (20% 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)

Marshall Field's Department Store Premium Oversized Sweatshirt

TeeArcade84

$51.67

~~$64.59~~ (20% off)

Good Better Best Chicago Bears Premium Oversized Hoodie

Miarsabhoul

$57.36

~~$76.48~~ (25% off)

Become a member.Get 25% off your first order.Plus other neat perks and exclusive savings to help you find the very thing.

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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Chicago Sweatshirts & Hoodies

Worldwide Shipping

Secure Payments

Free Return

Local Support

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