Chicago, Illinois — The Beginning of Route 66
The journey begins in Chicago.
Celebrate the starting point of America's most legendary highway with Chicago, Illinois — Destination No. 1 of 36 in the Historic Route 66 Destination Collection™.
This richly detailed heritage design captures the spirit of Chicago and the beginning of America's Main Street. The Chicago skyline, vintage theater marquee, classic American convertible, historic Route 66 signage, and the unmistakable U.S. Route 66 shield come together in a bold Americana-style illustration honoring the city where the westbound journey began.
Choose the timeless Historic Edition or commemorate the 100th Anniversary of Route 66, 1926–2026, with the special Centennial Edition featuring the Route 66 100 Years badge.
Shirt Details
🛢 Gildan G640 Softstyle® short sleeve shirt
🛢 Maroon color selected to complement the vintage Route 66 artwork
🛢 Soft, comfortable everyday fit
🛢 Detailed full-color front design
🛢 Unisex sizing
🛢 Designed and printed in the USA
Artwork Highlights
🛢 Chicago, Illinois destination artwork
🛢 Historic U.S. Route 66 shield
🛢 Chicago skyline inspiration
🛢 Vintage Chicago theater marquee
🛢 Classic American convertible
🛢 Historic Route 66 beginning signage
🛢 Destination No. 1 of 36
🛢 Optional 100 Years | 1926–2026 Centennial Edition
About the Historic Route 66 Destination Collection™
The Historic Route 66 Destination Collection™ is a special 36-shirt destination series honoring legendary communities along America's Main Street.
Beginning in Chicago, Illinois, and traveling west toward Santa Monica, California, each original design celebrates a historic Route 66 destination and its numbered place within the collection.
Chicago, Illinois is Destination No. 1 of 36 — where the journey begins.
For 2026, each destination is also available as a special Route 66 Centennial Edition, commemorating the 100th Anniversary of Route 66 — 1926–2026.
Choose the Historic Edition for a timeless Route 66 design or the Centennial Edition to mark this once-in-a-century milestone.
Perfect For
🛢 Route 66 travelers and road trip enthusiasts
🛢 Chicago residents and visitors
🛢 Illinois history fans
🛢 Classic car enthusiasts
🛢 Americana collectors
🛢 Route 66 memorabilia collectors
🛢 Centennial collectors
🛢 Anyone ready to begin the journey west
Care Instructions
🛢 Machine wash cold, inside out
🛢 Wash with similar colors
🛢 Tumble dry low
🛢 Do not iron directly over the artwork
🛢 Do not dry clean
Sizing
Unisex sizing. For the best fit, compare your favorite shirt with the available size chart before ordering.
Fulfillment
🛢 Made to order by Oak & Iron Gifts™
🛢 Ships within 48 hours in most cases
🛢 Carrier transit times are outside of our control
Historic Route 66 Destination Collection™
Chicago, Illinois — Destination No. 1 of 36
Historic Edition or 100 Years of Route 66 | 1926–2026 Centennial Edition
Built from Oak. Reinforced with Iron.™
Thank you for supporting Oak & Iron Gifts™, an American company.
