Part of Our Route 66 Everytown Collection | Chicago Edition
Chicago, Illinois: Eastern Terminus of Route 66
Every Route 66 road trip starts here. From the “Begin Route 66” sign in the shadow of the Art Institute to the neon glow of Lou Mitchell’s, Chicago is where 2,448 miles of American highway roll west out of Illinois toward the Pacific.
Celebrate Chicago’s place in Route 66 history with a vintage-inspired tee that honors the towns, landmarks and communities that made the Mother Road legendary. Part of the Route 66 Everytown Collection: one tee for every town that ever called the road home. Start with Chicago, then collect the entire route.
- Bella+Canvas 3001 unisex tee, true to size (see size charts in product image gallery)
- Solid colors: 100% Airlume combed and ring-spun cotton
- Heather colors: 52% cotton, 48% polyester
- Black Heather: 90% cotton, 10% polyester
- Side seams for structure, tear-away label for comfort
- Printed and fulfilled in the USA
- Free U.S. Shipping on orders of $25 or more, applied automatically
About Chicago, Illinois: Where the Mother Road Begins
Incorporated as a town in 1833 and as a city in 1837, Chicago grew from a muddy trading post on Lake Michigan into America’s great crossroads of rail, river and road. When U.S. Route 66 was designated in 1926, the city became the eastern starting line for travelers chasing opportunity all the way to Santa Monica.
The original 1926 terminus was at Jackson Boulevard and Michigan Avenue. As downtown traffic patterns changed, the official westbound start later shifted to Adams Street, where the well-known “Begin Route 66” sign now stands across from the Art Institute of Chicago.
For a true taste of the old road, Lou Mitchell’s has been serving travelers on Jackson Boulevard since 1923. It is known for hearty breakfasts, a classic neon sign and the free donut holes it hands to guests, so many road-trippers make it their first stop before heading west.
Beyond the sign, Chicago’s skyline tells its own story of ambition. The views from Willis Tower, the architecture lining the Chicago River and the shores of Lake Michigan give the start of Route 66 a big-city send-off no other town can match.
Each year, travelers from around the world gather at the sign to take the first photo of their journey. With the Route 66 Centennial arriving in 2026, Chicago remains the ceremonial gateway to the Main Street of America.
Wear a piece of the Mother Road’s history. Add this Chicago Route 66 collector’s tee to your cart, then explore every Illinois town featured in our Route 66 Everytown Collection.
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
