Part of Our Route 66 Everytown Collection - Chicago Edition
Bold, gritty and unapologetically real, this Chicago tee doesn't shy away from the Windy City's reputation. Branded for decades as the "Homicide Capital of the USA," Chicago's story is one of sharp contrasts: world-class art and architecture standing alongside headlines that shock the nation. This design captures that raw energy: the mix of beauty, struggle, resilience and the American way which define Chicago and its place on the Mother Road.
Made from ultra-soft, 100% Airlume combed and ring-spun cotton, this unisex jersey tee delivers comfort with a side of attitude. Whether you're kicking off a road trip, navigating the streets of Chicago or collecting tees from every town in our exclusive Route 66 Everytown Collection, this t-shirt is guaranteed to turn heads and start conversations.
Shop now at Heart of The Mother Road and enjoy FREE SHIPPING on all orders over $25.
About Chicago, Illinois: The Start of the Mother Road Can Be Treacherous
Chicago, Illinois is the legendary eastern terminus of Route 66 and the place where countless adventures have begun since 1926. The road officially starts at Grant Park on Adams St. and Michigan Ave., where the iconic "Begin Route 66" sign still invites travelers to launch their westward pilgrimage.
Founded in 1833, Chicago grew from a frontier outpost into one of America's most important cultural and industrial cities and a true gateway to the West. Its influence stretches far beyond Route 66, shaping art, architecture, music and cuisine.
Today, Route 66 wanderers can still experience some of the city's most iconic stops. Lou Mitchell's Restaurant continues its long tradition of serving hearty breakfasts to travelers eager to hit the road. The Art Institute of Chicago offers a moment of quiet reflection, with masterpieces like Edward Hopper's Nighthawks evoking the late-night diners that dot the Mother Road. Just steps away, Grant Park and the grand Buckingham Fountain provide the perfect send-off, offering visitors a chance to take in all that Chicago has to offer before heading west.
Chicago is a city of bold contrasts: dazzling yet gritty, historic yet modern. This unapologetic mix of beauty and raw energy makes it the ultimate starting point for the journey down America’s most iconic highway.
Product Features:
- 100% Airlume combed and ring-spun cotton for premium softness
- Side seams for added structure and durability
- Tear-away label for comfort
- Classic crew neckline with a flattering unisex fit - true-to-size for all day comfort (see size chart for details)
- Fulfilled in the USA
Care Instructions:
- Machine wash: cold (max 90°F / 30°C)
- Tumble dry: low heat
- Non-chlorine bleach as needed
- Iron or steam: medium heat
- Do not dry clean
