Everyone knows Route 66 ends at the Pacific. Fewer remember it begins in a canyon of Chicago skyscrapers — and that the first hundred miles, from the Loop to Pontiac, hold some of the best roadside Americana on the entire route. In the centennial year, this stretch has never looked better: new shield monuments, restored neon, and a 30-foot spaceman with a new home.
Here’s the local’s route, stop by stop, heading southwest. We’ve watched this road from our corner in Countryside for fifty years, so consider this the front-desk briefing.
Chicago: Where It All Begins
Start where the road does: the Begin Route 66 sign on Adams Street at Michigan Avenue, steps from the Art Institute’s lions. Get the photo early — the sidewalk fills up by mid-morning. The full story of the starting point is here. Then follow Ogden Avenue southwest out of the city, where new centennial wayfinding signs mark the historic alignment.
Cicero and Berwyn: The First Roadside Miles
The inner suburbs keep the working-class soul of the old road — classic drive-ins, vintage storefronts, and one of the sixteen new Route 66 Shield Monuments installed for the centennial in Berwyn.
Countryside: The Landmark at La Grange Road
Where Joliet Road meets La Grange Road stands a corner travelers have used as a waypoint since 1974: the William Tell Hotel, the Swiss-named landmark of the Chicago end of the route, now thoughtfully restored — and Countryside's own centennial shield monument, being installed for the centennial, will mark the alignment. It's also the logical overnight base for this whole list: everything below is an easy day trip from here.
Check Availability at the William Tell Hotel
Willowbrook: Dell Rhea’s Chicken Basket
Five minutes down Joliet Road sits one of the most beloved eateries on all 2,448 miles: Dell Rhea’s Chicken Basket, frying chicken for Route 66 travelers since the 1940s and listed on the National Register of Historic Places. Order the basket. Everyone does. There’s a reason.
Joliet: Prison Gates and a Giant Guitar
Joliet packs three stops into one town. The Old Joliet Prison — its gates made famous by The Blues Brothers — now welcomes visitors and photographers. The Illinois Rock and Roll Museum announces itself with the Gigantar, a 24-foot guitar-shaped sign. And the Broadway Greenway adds restored neon and murals for the centennial.
Wilmington: The Gemini Giant
Thirty feet of fiberglass spaceman, holding a rocket, wearing a welder’s helmet: the Gemini Giant is the most photographed resident of Will County. Relocated to South Island Park for the centennial, with the Landing Pad souvenir shop nearby, he’s the halfway point of a perfect day trip.
Dwight and Pontiac: Murals and the Hall of Fame
Push another half hour and you reach Dwight’s restored Ambler’s Texaco station and Pontiac, where more than twenty murals — including the giant Route 66 shield mural, one of the most photographed backdrops on the route — surround the Route 66 Association Hall of Fame & Museum.
Planning Your Route 66 Day Trip
The honest advice: don’t do this from a downtown Chicago hotel. You’ll spend an hour escaping the city each way. Base at the start of the open road instead — Countryside sits on the route itself, 25 minutes from the Begin sign in one direction and pointed at everything else in the other. Sleep on Route 66, wake up on Route 66, drive Route 66.
Timing your trip around a centennial event? The 2026 calendar is here.
Frequently Asked Questions
What are the best Route 66 attractions in Illinois near Chicago?
Within an easy day trip of Chicago: the Begin Route 66 sign downtown, Dell Rhea’s Chicken Basket in Willowbrook, the Old Joliet Prison and Illinois Rock and Roll Museum in Joliet, the Gemini Giant in Wilmington, and Pontiac’s Route 66 murals and Hall of Fame Museum.
How long is Route 66 in Illinois?
About 300 miles, from downtown Chicago to the Mississippi River at East St. Louis. The first hundred miles — Chicago to Pontiac — hold the densest cluster of classic attractions.
Can you do Illinois Route 66 in one day?
The Chicago-to-Pontiac stretch works well as a single day: roughly two hours of driving each way plus stops. Basing overnight on the route in the southwest suburbs, rather than downtown, saves an hour of city traffic in each direction.
What is the Gemini Giant?
A 30-foot fiberglass “Muffler Man” spaceman that has guarded Wilmington, Illinois since the 1960s. For the Route 66 centennial he was relocated to South Island Park in Wilmington, where he remains the route’s most photographed Illinois resident.
Where should you stay for an Illinois Route 66 road trip?
The William Tell Hotel in Countryside sits directly on the historic alignment at Route 66 and La Grange Road — a landmark since 1974, with Tell’s Tavern on site and every stop on this list within a day trip.