Skip to content
  1. FAST SHIPPING ON ALL ORDERS
  2. HAVE IT SHIPPED OR PICKED UP IN STORE
  3. CALL US: 312-641-6106

CHECK OUT OUR DISCOUNT SECTION

City of Chicago

City of Chicago

Wear the heart of the city on your sleeve with our official City of Chicago collection. Whether you’re a lifelong local or a visitor with love for the 312, this line captures the grit, pride, and timeless style of the Windy City. From flag-inspired designs to iconic skyline prints, shop gear that celebrates Chicago’s unique identity.

Apparel inspired by the Chicago city flag and skyline

Chicago-themed hoodies, hats, and t-shirts

Great for locals, tourists, and proud Chicagoans everywhere

Designed with Chi-Town pride

Show your love for the city that works - Chicago born, Chicago proud.

22 products

Clear all

  • New

Fire New Era Logo Beanie

A beige baseball cap viewed from the back, featuring thin navy blue pinstripes and a matching beige adjustable strap with a dark navy button on top. A structured baseball cap with a cream-colored front panel featuring thin navy blue pinstripes and large embroidered 'CHICAGO' lettering in navy blue. The cap has a solid navy blue curved brim and matching navy blue button on top.

Chicago Big Letter Pinstripe Hat

A black washed baseball cap shown from the back, featuring a white embroidered square patch with a monogram and the text 'ROBIN RUTH' on the crown, and 'CHICAGO' embroidered in white on the back strap. A black distressed baseball cap featuring 'CHICAGO Original' embroidered on the front. The 'CHICAGO' text is filled with a distressed, multi-colored pattern of red, pink, and white, while 'Original' is embroidered in white below it.

Chicago Black Floral Cap

White baseball cap shown from the back, featuring a square patch with the Robin Ruth logo and 'CHICAGO' embroidered on the strap. A white distressed baseball cap featuring 'CHICAGO' embroidered in colorful floral-patterned letters and 'Original' in gold below it, shown against a plain white background.

Chicago White Floral Hat

Back view of a beige mesh trucker cap with a beige adjustable strap and a small blue button on top. A gray and blue trucker hat with beige mesh back panels, featuring an embroidered patch of the Chicago city flag on the front.

Chicago Flag Trucker Patch Hat

Back view of a beige mesh trucker cap with a beige adjustable strap and a small blue button on top. A blue and beige trucker hat featuring a rectangular patch of the Chicago city flag on the front, set against a plain white background.

Chicago Flag Trucker Patch Hat - Ocean

Black baseball cap viewed from the back, featuring a perforated crown and an adjustable snapback closure with the brand name 'PACIFIC' debossed on the strap. A black structured snapback cap featuring an embroidered rectangular patch of the Chicago city flag on the front panel, set against a plain white background.

Chicago Flag Weekender Hat

The back view of a dark navy blue baseball cap with perforated panels and an adjustable snapback closure, shown on a plain white background. A navy blue trucker-style cap featuring an embroidered patch of the Chicago city flag on the front, with a white accent stripe across the brim, shown against a plain white background.

Chicago Flag Weekender Rope Hat - Navy

A light pink baseball cap with 'CHICAGO' embroidered in gray varsity letters outlined in white on the front, shown on a plain white background. A light pink baseball cap featuring 'CHICAGO' embroidered in varsity-style block letters with a gray outline on the front panel, set against a plain white background.

Chicago Bold Double Stitch Cap

A black baseball cap featuring the word 'CHICAGO' embroidered in arched varsity-style block letters across the front. The letters are beige/tan with a white outline, set against a clean white background. A black baseball cap featuring 'CHICAGO' embroidered in beige block letters with a white outline on the front panel, set against a plain white background.

Chicago Bold Double Stitch Black Cap

A washed dark gray baseball cap featuring 'CHICAGO' embroidered in black arched lettering with a white outline, and 'Original 1837' in tan below it, shown on a plain white background. Dark blue cap with mesh ventilation on a white background

Chicago Arch Original Grey Hat

  • On Sale

Chicago Glitter Flag Trucker Hat (D) - Grey

  • On Sale

Chicago Glitter Flag Trucker Hat (D) - Royal

Chicago Upside Down Natural Hat - Natural/Navy

Chicago Upside Down Natural Hat - Natural/Black

Chicago High Arch Structured Cap

Chicago Grey/White Flag Trucker Cap

Chicago Leather Flag Patch Navy Trucker

Showing 18 of 22