Chicago Men's Hats

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  • MENS - Gratitude Chicago Retro Trucker Hat - Black/Blue

    Gratitude Chicago Retro Trucker Hat

    Men's Black/Blue
    50% off
    Sale
  • ADULT - New Era Cubs 59Fifty Felt Fitted Cap - Black/White

    New Era Cubs 59Fifty Felt Fitted Cap

    Adult Black/White     $50
  • ADULT - New Era Cubs 59Fifty Felt Fitted Cap - Blue

    New Era Cubs 59Fifty Felt Fitted Cap

    Adult Blue     $50
  • ADULT - New Era Cubs 59Fifty Authentic Cap - Royal/Red White

    New Era Cubs 59Fifty Authentic Cap

    Adult Royal/Red White     $50
  • MENS - New Era Chicago Bulls NBA 25 Golfer Cap - White/Black

    New Era Chicago Bulls NBA 25 Golfer Cap

    Men's White/Black     $43
  • MENS - New Era Cubs Vintage Landscape Cap - White/Blue

    New Era Cubs Vintage Landscape Cap

    Men's White/Blue     $34
  • MENS - New Era Cubs Vintage Landscape Cap - Brown/White

    New Era Cubs Vintage Landscape Cap

    Men's Brown/White     $34
  • MENS - New Era White Sox 59Fifty City Connect Fitted Cap - Multi

    New Era White Sox 59Fifty City Connect Fitted Cap

    Men's Multi
    24% off
    Sale
  • ADULT - New Era White Sox 59Fifty Felt Fitted Cap - Black

    New Era White Sox 59Fifty Felt Fitted Cap

    Adult Black     $50
  • MENS - New Era White Sox 59Fifty 95th Cap - Blue/Multi

    New Era White Sox 59Fifty 95th Cap

    Men's Blue/Multi     $45
  • ADULT - New Era White Sox 59Fifty Authentic Cap - Multi/Navy

    New Era White Sox 59Fifty Authentic Cap

    Adult Multi/Navy     $50
  • ADULT - New Era Cubs 5950 Evergreen Side Patch Fitted Hat - White/Black

    New Era Cubs 5950 Evergreen Side Patch Fitted Hat

    Adult White/Black
    32% off
    Sale
  • MENS - New Era Cubs 59Fifty 90 ASG Cap - Blue/Multi

    New Era Cubs 59Fifty 90 ASG Cap

    Men's Blue/Multi     $45
  • ADULT - New Era White Sox 5950 Fitted Hat - Dark Green/White

    New Era White Sox 5950 Fitted Hat

    Adult Dark Green/White
    64% off
    Sale
  • ADULT - New Era White Sox 5950 Fitted Hat - Gray/White

    New Era White Sox 5950 Fitted Hat

    Adult Gray/White
    29% off
    Sale
  • ADULT - New Era White Sox 5950 Fitted Hat - White/Stone

    New Era White Sox 5950 Fitted Hat

    Adult White/Stone
    29% off
    Sale
  • MENS - New Era Cubs 9FIFTY A-Frame Banner Cap - Multi/Tan

    New Era Cubs 9FIFTY A-Frame Banner Cap

    Men's Multi/Tan     $38
  • MENS - New Era White Sox Evergreen Trucker Hat - Black/White

    New Era White Sox Evergreen Trucker Hat

    Men's Black/White
    32% off
    Sale
  • MENS - New Era Cubs 9FORTY MC A-Frame Cap - Tan/Multi

    New Era Cubs 9FORTY MC A-Frame Cap

    Men's Tan/Multi     $35
  • MENS - New Era Cubs 9FIFTY A-Frame Chain Cap - Tan/Multi

    New Era Cubs 9FIFTY A-Frame Chain Cap

    Men's Tan/Multi     $40
  • MENS - New Era White Sox ACPERF Hat - Black/White

    New Era White Sox ACPERF Hat

    Men's Black/White     $50
  • MENS - New Era Cubs Player Replica 9FORTY Cap - Blue/Red

    New Era Cubs Player Replica 9FORTY Cap

    Men's Blue/Red     $35
  • MENS - 47 Brand Cubs Hitch Cap - Khaki

    47 Brand Cubs Hitch Cap

    Men's Khaki     $40
  • MENS - 47 Brand Cubs Hitch Cap - Black/White

    47 Brand Cubs Hitch Cap

    Men's Black/White     $40
  • MENS - 47 Brand Cubs Hitch Cap - Red/White

    47 Brand Cubs Hitch Cap

    Men's Red/White     $40
  • MENS - New Era Cubs 9FORTY MC A-Frame Arch Cap - Blue

    New Era Cubs 9FORTY MC A-Frame Arch Cap

    Men's Blue     $35
  • ADULT - New Era White Sox 75th Anniversary Stone Hat - Gray/Black

    New Era White Sox 75th Anniversary Stone Hat

    Adult Gray/Black     $42
  • MENS - New Era White Sox State Flower Cap - White/Black

    New Era White Sox State Flower Cap

    Men's White/Black     $38
  • MENS - New Era White Sox State Flower Cap - White/Green

    New Era White Sox State Flower Cap

    Men's White/Green     $38
  • ADULT - 47 Brand White Sox Hitch Cap - White/Grey

    47 Brand White Sox Hitch Cap

    Adult White/Grey     $40
  • ADULT - 47 Brand White Sox Hitch Cap - Black/White

    47 Brand White Sox Hitch Cap

    Adult Black/White     $40
  • ADULT - 47 Brand White Sox Hitch Cap - Khaki

    47 Brand White Sox Hitch Cap

    Adult Khaki     $40
  • MENS - New Era White Sox 5950 '05 WS Cap - White/Black

    New Era White Sox 5950 '05 WS Cap

    Men's White/Black     $45
  • ADULT - New Era White Sox 9Fifty AF Curve 95th Cap - Multi/Tan

    New Era White Sox 9Fifty AF Curve 95th Cap

    Adult Multi/Tan
    14% off
    Sale
  • MENS - New Era White Sox 950AF Curve 95th Anniversary Cap - Gray/Black

    New Era White Sox 950AF Curve 95th Anniversary Cap

    Men's Gray/Black     $35
  • MENS - New Era White Sox 9FIFTY A-Frame Cap - Beige/Brown

    New Era White Sox 9FIFTY A-Frame Cap

    Men's Beige/Brown     $35
  • MENS - New Era White Sox 950AF Curve '05 World Series Cap - Carolina

    New Era White Sox 950AF Curve '05 World Series Cap

    Men's Carolina     $35
  • MENS - New Era Cubs 9FIFTY A-Frame EG Cap - Blue

    New Era Cubs 9FIFTY A-Frame EG Cap

    Men's Blue
    32% off
    Sale
  • ADULT - New Era Cubs 9Forty Player Weekend Cap - Multi

    New Era Cubs 9Forty Player Weekend Cap

    Adult Multi     $38
  • MENS - New Era White Sox 9FIFTY A-Frame Curve 05 WS Cap - White/Black Orange

    New Era White Sox 9FIFTY A-Frame Curve 05 WS Cap

    Men's White/Black Orange     $35
  • MENS - New Era White Sox ASG 50th Anniversary Cap - Black/Red

    New Era White Sox ASG 50th Anniversary Cap

    Men's Black/Red     $42
  • MENS - New Era White Sox 9Fifty A-Frame Curve '05 WS Cap - Navy/White

    New Era White Sox 9Fifty A-Frame Curve '05 WS Cap

    Men's Navy/White     $35
  • MENS - New Era White Sox Player Replica 9FORTY Cap - Black/White

    New Era White Sox Player Replica 9FORTY Cap

    Men's Black/White     $35
  • MENS - New Era White Sox 9FIFTY A-Frame EG Cap - Black

    New Era White Sox 9FIFTY A-Frame EG Cap

    Men's Black     $37
  • MENS - New Era Cubs 9SEVENTY SS 2T Trucker - Tan/Multi

    New Era Cubs 9SEVENTY SS 2T Trucker

    Men's Tan/Multi     $38
  • MENS - New Era White Sox Core Classic Replica Cap - Multi Coloe

    New Era White Sox Core Classic Replica Cap

    Men's Multi Coloe     $32
  • ADULT - New Era Chicago White Sox 5950 Evergreen Side Patch Fit - Black/White

    New Era Chicago White Sox 5950 Evergreen Side Patch Fit

    Adult Black/White
    32% off
    Sale
  • ADULT - New Era Chicago White Sox 5950 Evergreen Side Patch Fit - Red/White

    New Era Chicago White Sox 5950 Evergreen Side Patch Fit

    Adult Red/White
    32% off
    Sale

About Chicago Men's Hats


Discover the ultimate collection of Chicago men's hats, designed for style and comfort. Whether you're looking for a classic fitted cap or a trendy trucker hat, our selection has something for every fan. Each hat is crafted with quality materials to ensure durability and a perfect fit, making them ideal for everyday wear or game day excitement.

Show off your Chicago pride with hats that feature iconic logos and designs, perfect for any occasion. From casual outings to sporting events, these hats provide a stylish way to complete your look while keeping you comfortable. Elevate your accessory game with our diverse range of Chicago men's hats, tailored for every fan's unique style.