Chicago Sweatshirts & Hoodies

1000+ items

Vintage-Styled Bears Premium Oversized Hoodie

Daybreak Media

$43.19

~~$57.59~~ (25% off)

Da Beers Premium Oversized Hoodie

Greg Dressel

$43.19

~~$57.59~~ (25% off)

Columbia College Chicago Classic Logo High Quality Print Premium Oversized Hoodie

blomdel

$48.59

~~$64.79~~ (25% off)

CHICAGO FIRE - LT. SEVERIDE - SQUAD 3 Premium Oversized Sweatshirt

emilybraz7

$45.13

~~$60.19~~ (25% off)

Joe Cool Snoopy Chicago Bears Premium Oversized Sweatshirt

kittyr1na

$35.46

~~$47.29~~ (25% off)

Home CHICAGO Premium Oversized Sweatshirt

katieandrew

$38.37

~~$51.16~~ (25% off)

Philadelphia International Records Premium Oversized Sweatshirt

goatboyjr

$38.69

~~$51.59~~ (25% off)

The Chicago College Of Performing Arts Premium Oversized Sweatshirt

LinaRausch

$38.69

~~$51.59~~ (25% off)

Chicago Blackhawks Cross Stitch Premium Oversized Hoodie

ZamboniZingers

$43.19

~~$57.59~~ (25% off)

vintage chicago city Premium Oversized Hoodie

ajengsusan

$43.19

~~$57.59~~ (25% off)

Beers Premium Oversized Sweatshirt

Primotees

$35.46

~~$47.29~~ (25% off)

Derrick Rose Jersey Chicago Premium Oversized Sweatshirt

WonderBin

$38.69

~~$51.59~~ (25% off)

Jordan Air White Pullover Sweatshirt

TheUmbrrella

$31.49

~~$41.99~~ (25% off)

CHICAGO JAZZ FESTIVAL 2026 - Celebrating USA 250th Anniversary Premium Oversized Sweatshirt

DBM Photo Art 1

$40.30

~~$53.74~~ (25% off)

Monsters of the Midway Premium Oversized Sweatshirt

A Brand With No Name

$38.69

~~$51.59~~ (25% off)

Jeffery Simmons 99 Chicago Bears Football Vintage Graphic Premium Oversized Sweatshirt

Artify Works

$35.46

~~$47.29~~ (25% off)

Vintage Chicago Bears Lightweight Sweatshirt

nichemaps

$30.71

~~$38.39~~ (20% off)

Greatest Game Ever Played Premium Oversized Hoodie

CMDTs

$39.59

~~$52.79~~ (25% off)

Sweet Vintage Retro Chicago City Flag Bear Printa Premium Oversized Hoodie

DuneHaicna

$39.59

~~$52.79~~ (25% off)

Bear Down Pullover Hoodie

Primotees

$31.49

~~$41.99~~ (25% off)

SAIC skyline design 2 Premium Oversized Hoodie

Alana Palomo

$43.19

~~$57.59~~ (25% off)

Jeffery FREAKING Simmons PARODY Premium Oversized Hoodie

damgoodgame

$41.03

~~$54.71~~ (25% off)

Art by Shepard Fairey, Shepard Fairey Art urbain Premium Oversized Sweatshirt

Bob-Studio

$45.14

~~$60.19~~ (25% off)

DIVISION ST CHICAGO STREET SIGN Premium Oversized Sweatshirt

avshirts773

$38.69

~~$51.59~~ (25% off)

Bruin bear Premium Oversized Sweatshirt

sabinako

$35.46

~~$47.29~~ (25% off)

Cook County Illinois Sheriff Investigator Premium Oversized Sweatshirt

Lawrence Baird

$38.69

~~$51.59~~ (25% off)

CHICAGO MED LOGO Premium Oversized Sweatshirt

emilybraz7

$45.13

~~$60.19~~ (25% off)

Luther Allison - Chicago Blues fan Lightweight Hoodie

Sarcastic designs

$32.63

~~$40.79~~ (20% off)

I Survived The Polar Vortex - Funny Chicago Winter Humor Premium Oversized Hoodie

aligchi

$43.55

~~$58.07~~ (25% off)

Sugar Skull Chicago Baseball Premium Oversized Hoodie

shanconart

$44.99

~~$59.99~~ (25% off)

Chicago Minimalist Map United States Premium Oversized Sweatshirt

BoringClothes

$35.46

~~$47.29~~ (25% off)

Loyola University Chicago Premium Oversized Sweatshirt

brooklevan

$39.88

~~$53.18~~ (25% off)

The Blues Brothers Classic Movie Pullover Sweatshirt

Kabege-Arts

$37.52

~~$50.04~~ (25% off)

iga Premium Oversized Sweatshirt

Gio Wonder

$44.49

~~$59.33~~ (25% off)

NY Marathon Finisher Premium Oversized Hoodie

imrhouzvecxs

$48.59

~~$64.79~~ (25% off)

University of Chicago Premium Oversized Hoodie

Ellery Lapin

$52.19

~~$69.59~~ (25% off)

CHICAGO P.D - DETECTIVE JAY HALSTEAD - INTELLIGENCE BADGE VEST Pullover Hoodie

emilybraz7

$36.73

~~$48.99~~ (25% off)

Reader Logo Through the Years Premium Oversized Hoodie

The Chicago Reader

$43.19

~~$57.59~~ (25% off)

Coach Ben Johnson Good, Better, Best Win Speech Art Lightweight Sweatshirt

Bear Creative

$26.39

~~$32.99~~ (20% off)

University of Chicago Premium Oversized Sweatshirt

carolinezhao

$38.69

~~$51.59~~ (25% off)

Chicago Park District (back) Lightweight Hoodie

adrien2297

$32.63

~~$40.79~~ (20% off)

Fire, Med, PD skyline white Premium Oversized Sweatshirt

ellclark

$40.30

~~$53.74~~ (25% off)

Southside with Chicago flag stars Southside pride Premium Oversized Hoodie

snowry

$39.59

~~$52.79~~ (25% off)

Chicago Blues Premium Oversized Sweatshirt

samhi113

$38.62

~~$51.50~~ (25% off)

Connor Bedard Draft Art Premium Oversized Sweatshirt

B3 Graphics

$36.11

~~$48.15~~ (25% off)

Ferris Bueller at the Art Museum Premium Oversized Hoodie

comfysockz

$41.39

~~$55.19~~ (25% off)

Ragtime Musical Hi-Res Premium Oversized Hoodie

blomdel

$48.59

~~$64.79~~ (25% off)

Chicago Skyline Cubs CHI Chi-Town Cityscape (Red & White) Premium Oversized Sweatshirt

pixeljamz

$40.30

~~$53.74~~ (25% off)

The Chicago College, of Performing Arts Premium Oversized Sweatshirt

NoraroN

$38.69

~~$51.59~~ (25% off)

End of Beginning Premium Oversized Sweatshirt

djokeerydaily

$38.69

~~$51.59~~ (25% off)

Dennis Rodmans Green Hair Worm Premium Oversized Sweatshirt

AbbelSwords

$38.69

~~$51.59~~ (25% off)

Random Fuego Destruction Dresden Files Harry Zipped Hoodie

idwearit

$38.39

~~$47.99~~ (20% off)

Chicago – Travel Art Premium Oversized Hoodie

maximinano100k

$39.59

~~$52.79~~ (25% off)

Chicago Skyline Bulls CHI Chi-Town Cityscape (Red & White) Premium Oversized Sweatshirt

pixeljamz

$40.30

~~$53.74~~ (25% off)

Filipino School of Chicago Premium Oversized Hoodie

Fil-School-Chi

$43.19

~~$57.59~~ (25% off)

Columbia College Chicago Flag Logo Premium Oversized Sweatshirt

hanhorton

$38.69

~~$51.59~~ (25% off)

chicago fire cast-members Premium Oversized Sweatshirt

LondownDesign

$41.91

~~$55.89~~ (25% off)

Original Chicagoland Beef Company Premium Oversized Sweatshirt

MalmoDesigns

$45.14

~~$60.19~~ (25% off)

UIC College of Medicine Premium Oversized Hoodie

Nicole Christine

$48.59

~~$64.79~~ (25% off)

Chicago FC United logo usl Premium Oversized Hoodie

chcasey

$43.19

~~$57.59~~ (25% off)

Sweet Home Chicago Design Premium Oversized Hoodie

aligchi

$43.55

~~$58.07~~ (25% off)

Chicago Flags with Teams and Skyline Premium Oversized Hoodie

kwald12

$41.39

~~$55.19~~ (25% off)

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

Dennisust

$31.49

~~$41.99~~ (25% off)

Chicago Football Heartbeat Pulse Premium Oversized Sweatshirt

Bored Imagination

$35.46

~~$47.29~~ (25% off)

Columbia College Chicago Premium Oversized Sweatshirt

blomdel

$43.52

~~$58.04~~ (25% off)

Decatur Staleys Premium Oversized Sweatshirt

Retrorockit

$38.69

~~$51.59~~ (25% off)

Drose Day 1.4.25 Premium Oversized Sweatshirt

mysports

$41.91

~~$55.89~~ (25% off)

SIX The Musical Queens Silhouettes— With Lyrics! Pullover Sweatshirt

broadway-babies

$31.49

~~$41.99~~ (25% off)

Chicago Med tv show characters poster logo Premium Oversized Hoodie

AnsykD

$48.59

~~$64.79~~ (25% off)

Joffrey Ballet Sign Chicago Premium Oversized Sweatshirt

Enzwell

$38.69

~~$51.59~~ (25% off)

School of the Art Institute of Chicago (SAIC) Lightweight Hoodie

HayleeC34

$29.91

~~$37.39~~ (20% off)

Kanye West Dropout Bear Chicago Vintage Graduation Premium Oversized Sweatshirt

shopvinhcong

$45.14

~~$60.19~~ (25% off)

Chicago Trains Map Premium Oversized Sweatshirt

Rich Anderson

$38.69

~~$51.59~~ (25% off)

Chicago Bears Good Better Best by Coach Johnson on Colour Background Premium Oversized Hoodie

Bear Creative

$39.59

~~$52.79~~ (25% off)

Chicago - The Musical/Movie Premium Oversized Hoodie

thefilmmagazine

$43.55

~~$58.07~~ (25% off)

Filipino School of Chicago White Logo Premium Oversized Hoodie

Fil-School-Chi

$43.19

~~$57.59~~ (25% off)

CHICAGO P.D - SERGEANT HANK VOIGHT - INTELLIGENCE BADGE VEST Premium Oversized Hoodie

emilybraz7

$50.39

~~$67.19~~ (25% off)

chief keef Classic T-Shirt Copy Copy Premium Oversized Sweatshirt

Janensidine

$41.91

~~$55.89~~ (25% off)

Good Better Best Never Let it Rest - Chicago Bears Premium Oversized Hoodie

Primotees

$39.59

~~$52.79~~ (25% off)

Chicago the Musical Premium Oversized Hoodie

Rasiadunn

$43.19

~~$57.59~~ (25% off)

House Music - Vintage Retro Hexagon Premium Oversized Sweatshirt

Jam Jar

$42.88

~~$57.18~~ (25% off)

Marshall Field's Department Store Premium Oversized Sweatshirt

TeeArcade84

$40.30

~~$53.74~~ (25% off)

mt joy - hippi van bus Premium Oversized Hoodie

LondownDesign

$46.79

~~$62.39~~ (25% off)

Joffrey Ballet Sign Night Premium Oversized Sweatshirt

Enzwell

$38.69

~~$51.59~~ (25% off)

Chicago Fire Premium Oversized Sweatshirt

lemonlimeyogurt

$38.04

~~$50.73~~ (25% off)

CHICAGO MED - WILL HALSTEAD - SCRUBS - EMERGENCY MEDICINE Premium Oversized Hoodie

emilybraz7

$50.39

~~$67.19~~ (25% off)

Chicago Park District Lightweight Hoodie

adrien2297

$32.63

~~$40.79~~ (20% off)

Luther Burden III Choke Premium Oversized Hoodie

RatTrapTees

$39.59

~~$52.79~~ (25% off)

Fuck Fame Chicago Pullover Hoodie

TheLaw61

$32.28

~~$43.04~~ (25% off)

Buzz’n Bear Lightweight Hoodie

Illannoyed

$31.54

~~$39.43~~ (20% 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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