Short answer: the Begin Route 66 sign stands on Adams Street just west of Michigan Avenue, in the heart of downtown Chicago, across from the Art Institute. That’s where 2,448 miles of the Mother Road officially begin their run to Santa Monica.
Longer answer: it’s complicated, in the way all good road stories are. Here’s the history, the photo advice, and what to do with your first miles west — from a hotel that’s been watching traffic come off this road since 1974.
The Official Answer, and the Historical One
When Route 66 was commissioned on November 11, 1926, its eastern terminus was at Jackson Boulevard and Michigan Avenue. Decades later, Chicago’s downtown streets went one-way — Adams westbound, Jackson eastbound — so the route out of the city shifted one block north to Adams.
That’s why today you’ll find two signs: “Begin Route 66” on Adams (your westbound start) and “End Route 66” on Jackson (for travelers finishing the eastbound run). Purists note the 1926 start; photographers line up on Adams. Both are right.
Getting the Photo
- The sign sits on the north side of Adams at Michigan — arrive before mid-morning to beat the crowds, especially in the centennial year.
- Pair it with the Art Institute lions a few steps away; two icons, one block.
- Grant Park and Buckingham Fountain, long treated as the route’s symbolic front porch, are a short walk east if you want the full send-off.
Your First Miles West
From Adams, the historic route works southwest out of the Loop and picks up Ogden Avenue, where new centennial wayfinding signs now mark the alignment through the near-west suburbs. From there it's Joliet Road through Countryside — past our front door — and on toward Willowbrook, Joliet, and the Gemini Giant.
Stay on Route 66 in Countryside
Here’s the trip-planning insight most first-timers miss: downtown Chicago is a place to visit the start, not to start the drive. Stay on the route itself in the southwest suburbs, day-trip into the Loop for the sign (25 minutes by car, or the Metra from La Grange), and begin the actual road trip from your hotel parking lot — already on Route 66.
Read more: The William Tell Hotel: fifty years on the Mother Road, and stay on Route 66 in Countryside.
The Centennial Year Matters
Route 66 turns 100 on November 11, 2026, and Illinois is celebrating all year — which means the Begin sign will see its biggest crowds in decades. If the centennial is your reason for the trip, our full guide to the year’s events is here: Route 66 centennial events in Illinois.
Frequently Asked Questions
Where exactly is the Begin Route 66 sign?
On Adams Street just west of Michigan Avenue in downtown Chicago, across from the Art Institute of Chicago. It marks the westbound start of the historic route.
Is there parking near the Route 66 start sign?
Downtown garages exist but are expensive. Many visitors stay in the suburbs on the route and take the Metra in — the BNSF line from La Grange arrives at Union Station, a short walk from the sign.
Where does Route 66 end?
At the Pacific Ocean in Santa Monica, California — 2,448 miles from Adams Street.
What's the first classic Route 66 stop after leaving Chicago?
Following Ogden Avenue and Joliet Road southwest, the first cluster comes quickly: the historic corridor through Berwyn and Countryside — home of the William Tell Hotel, on the route since 1974 — then Dell Rhea’s Chicken Basket in Willowbrook, frying chicken for travelers since the 1940s.
Why does Route 66 start on Adams but end on Jackson?
The original 1926 terminus was Jackson Boulevard at Michigan Avenue. When downtown streets became one-way, westbound traffic moved to Adams Street — so today Adams carries the Begin sign and Jackson the End sign.