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Chicago Skyline Caps
1000+ items
Hats
Filters (2)
1000+ items
Newest
Chicago Skyline with Flags and Sports Team Symbols Artistic Design Baseball Cap
TeesITnMeanIT
$27.29
Chicago-Skyline-&-Flag-Art Baseball Cap
ErikKuhl
$23.09
Redlines Charge Chicago Bull Basketball Mascot Dynamic Dad Hat
BUDKAA
$23.09
Chicago Colorful Folk Art | Vibrant Skyline Lakefront Design for Fashion & Home Decor Dad Hat
Imaginarium of Chaos falcon88
$27.99
Illinois Heartland Horizons – Vintage State Travel Poster with Chicago Skyline Dad Hat
RockitBaby
$25.19
Chicago Illinois, Usa City Skyline Travel Souvenir Dad Hat
AncientClouds25
$29.39
Chicago T Rex Reaching for an Autumn Leaf Baseball Cap
Soft Paws Sketches
$25.19
Chicago Black and White Zoom Lens Reflection Baseball Cap
Numerous-Niches
$23.09
Chicago Recycle Collage Skyline | 90s Torn Paper Cutout Art Baseball Cap
Robert Lucio
$25.19
Chicago Vintage Film Camera Reflection Dad Hat
Numerous-Niches
$23.09
Illinois Chicago Raccoon Deep Dish Pizza – Deeper Opinions Dad Hat
TheTrendsDesk
$25.19
Chicago – Travel Art Baseball Cap
maximinano100k
$28.34
Captain Chicago Vintage Style Urban Hero Design Dad Hat
Koodolabs
$25.19
Illinois Grunge Skyline | Black and White Chicago Urban Art Baseball Cap
Paper Drip
$24.14
Illinois Vintage Skyline | Distressed American Flag Chicago Art Baseball Cap
Paper Drip
$24.14
Illinois Chicago Skyline | Chicago Flag Stars and River Cityscape Dad Hat
Paper Drip
$24.14
Chicago Football City Skyline Graphic Design for Sports Fans Dad Hat
TroskyDesign
$25.19
Retro Chicago Skyline Silhouette Vintage Cityscape Design Baseball Cap
Zinebaarich
$25.19
Chicago Skyline Silhouette with Iconic Cityscape and Architectural Landmarks Baseball Cap
Zinebaarich
$25.19
Chicago Cityscape Skyline Design with Urban Vibes and Iconic Architecture Dad Hat
Zinebaarich
$25.19
Chicago Football City Skyline Sports Fan Design Dad Hat
TroskyDesign
$25.19
Chicago Windy City Skyline Sticker with Iconic Landmarks Dad Hat
Zinebaarich
$25.19
Chicago Skyline Illustration with Iconic Cityscape and Architectural Landmarks Dad Hat
Zinebaarich
$25.19
Chicago Skyline with Lake Michigan and Water Reflections Artistic Design Baseball Cap
Zinebaarich
$25.19
Chicago Skyline Silhouette with Iconic Architecture and Cityscape Design Dad Hat
Zinebaarich
$25.19
I Love Chicago Heart City Skyline Design Baseball Cap
Zinebaarich
$25.19
Chicago Skyline Silhouette Art Featuring Iconic Cityscape at Sunset Baseball Cap
Zinebaarich
$25.19
Chicago Cityscape Skyline Illustration with Iconic Architecture Dad Hat
Zinebaarich
$25.19
Chicago Skyline Art Print Featuring Iconic Cityscape Silhouette at Sunset Dad Hat
Zinebaarich
$25.19
Chicago Skyline Illustration with Iconic Cityscape and Urban Vibes Baseball Cap
Zinebaarich
$25.19
Chicago Skyline Illustration with Iconic Landmarks and Urban Vibes Baseball Cap
Zinebaarich
$25.19
Chicago Windy City Pattern featuring Iconic Skyline and Elements Baseball Cap
Zinebaarich
$25.19
Knuckles Chicago Illinois Red Sonic Style Character City Skyline Waterfront Scene Baseball Cap
Pliable
$25.19
Life Moves Pretty Fast Retro Baseball Cap
Quoteez
$23.09
Chicago Skyline Above Lake Michigan Dad Hat
Beyond Destinations
$23.30
Chicago Christmas Lights Skyline | Windy City Holiday Night Design Baseball Cap
Robert Lucio
$25.19
Chicago City of Architecture Vintage Skyline Design Baseball Cap
castillomiami
$26.24
Chicago Illinois USA City Of Big Shoulders Urban Travel Landmark Dad Hat
NeedForParks
$33.58
Chicago Marathon 2026 Dad Hat
Coakes7
$23.09
Chicago Illinois USA City Of Big Shoulders Travel Souvenir Local Resident Dad Hat
Simsimah26Parks
$41.98
Chicago Elevated L Train Vintage Travel Badge Dad Hat
Globalcitytees
$26.24
Chicago Football Shake and Bake Duo City Action Baseball Cap
RDGNR
$24.14
SoxTober Chicago White Sox Halloween Skyline Baseball Dad Hat
RDGNR
$24.14
Mike Ditka Legend Portrait With Inset And Skyline Baseball Cap
OrlandNienow
$25.19
Vintage Chicago Snow Globe Travel Badge Dad Hat
k3rstman1
$25.19
Chicago - That Toddlin' Town Dad Hat
Offset Vinyl Film
$25.19
Mike Ditka Legend Portrait Dual View Skyline Dad Hat
dtyqmen
$25.61
Chicago City of Winds and Dreams Skyline Badge Sticker Baseball Cap
obalartsMerch
$23.09
Mike Ditka Legend Portrait Dual View Skyline Dad Hat
bootycatclube
$25.19
Mike Ditka Da Coach Forever a Legend Portrait Baseball Cap
bootycatclube
$25.19
Mike Ditka Profile Portrait Chicago Skyline Dad Hat
bootycatclube
$25.19
Mike Ditka Profile Portrait Chicago Skyline Baseball Cap
bootycatclube
$25.19
Mike Ditka Da Coach Forever a Legend Skyline Dad Hat
bootycatclube
$25.19
Chicago South Side Vintage Baseball Skyline Baseball Cap
HadyaNasri
$25.19
TBT Chicago - Navy Pier - Centennial Wheel - Lake Michigan - Vintage Travel Postcard Baseball Cap
JEFFCORA
$25.19
Skyline of Chicago - Watercolor and pencil Dad Hat
kolonjArt
$27.29
TBT Chicago DuSable Bridge Chicago River Vintage Travel Postcard Baseball Cap
JEFFCORA
$25.19
Chicago-Bears-Football Baseball Cap
Fish.art
$25.19
TBT Chicago Wrigley Building Pop Art Vintage Travel Postcard Baseball Cap
JEFFCORA
$25.19
Chicago - Illinois - USA Dad Hat
GoodOldVintage
$24.77
Lollapalooza Chicago 2026 Summer Music Festival Baseball Cap
Lehungstore
$31.49
Chicago Bears Chicago Illinois Skyline Baseball Cap
crofts-haricex
$25.19
Chicago Styx Windy Cities Tour Rock Fans Baseball Cap
Lehungstore
$31.49
Chicago Styx Windy Cities Tour Music Fan Baseball Cap
Lehungstore
$31.49
Straight Outta Chicago Urban City Pride Design Baseball Cap
JesterVision
$30.44
Sweet Home Chicago Skyline Vintage Style Design for City Lovers and Nostalgic Fans Baseball Cap
JesterVision
$30.44
Chicago Football City Skyline Sports Fan Design Baseball Cap
MrMoremi
$30.44
Chicago City Archive Urban Architecture Vintage Graphic Baseball Cap
SplashTastic
$22.04
Vintage Chicago Optical Illusion Steampunk Skyline Dad Hat
Robert Lucio
$25.19
More for the City Collection... Dad Hat
Harold122Jade
$29.18
Bear Down Shield Bear Head Sunglasses Chicago Skyline Baseball Cap
purrinink
$25.19
Bear Down Bear Head Sunglasses Chicago Skyline Lenses Dad Hat
purrinink
$25.19
Bear Down Bear Head Sunglasses Chicago Skyline Lenses Baseball Cap
purrinink
$25.19
Chicago Skyline Minimalist Line Art Dad Hat
MinimalLine
$25.19
Chicago Pride Baseball Cap
Tara Collins
$23.09
Chicago Baseball Cap
Cole Design Works
$25.19
Illinois Vintage Travel Badge – The Prairie State Baseball Cap
BLUEFOX05
$29.39
Chicago Cityscape Skyline Artistic Illustration Design Dad Hat
LunaVeg
$33.16
City Life — Chicago Dad Hat
New-Blood
$23.09
chicago - usa Baseball Cap
zzinthestore
$25.19
chicago bears Baseball Cap
theandroidvivz
$25.19
chicago bears Dad Hat
theandroidvivz
$25.19
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