Route 66 begins in Chicago and travels southwest through Illinois, passing roadside landmarks, historic buildings, museums, murals and communities shaped by the Mother Road. Because the highway followed different alignments during different periods, there is no single modern road that reproduces every historic mile.
This guide follows a practical Chicago-to-Pontiac sequence, highlighting stops that travelers can consider along the way. It is an itinerary-planning guide rather than turn-by-turn navigation. Check each attraction’s official website for current hours, admission, accessibility and seasonal closures before leaving.
Quick Planning: Chicago to Pontiac
| Area | Suggested stop | Why consider it | Check before visiting |
|---|---|---|---|
| Chicago | Navy Pier ceremonial start and historic downtown start locations | Route 66 starting-point context | Parking, event access and preferred starting point |
| Countryside | Historic Joliet Road corridor | Convenient suburban waypoint | Current route map and road conditions |
| Willowbrook | Dell Rhea’s Chicken Basket | Historic Route 66 dining stop | Restaurant hours |
| Joliet | Old Joliet Prison | Historic site and guided/self-guided tours | Tickets and seasonal schedule |
| Wilmington | Gemini Giant | Roadside landmark at South Island Park | Park access and local notices |
| Dwight | Ambler’s Texaco Gas Station | Restored historic service station | Visitor-center hours |
| Pontiac | Route 66 museum and murals | Museum exhibits and walkable public art | Museum hours and temporary exhibit access |
Chicago: Where Route 66 Begins
Chicago now has three locations connected to the start of Route 66. Navy Pier serves as the route’s symbolic, ceremonial starting point, dedicated as part of the 2026 centennial. The familiar “Begin Route 66” sign remains near Adams Street and Michigan Avenue, close to the Art Institute. And the original 1926 eastern terminus is marked near Jackson Boulevard and Michigan Avenue. Each has its own history and none has fully replaced the others. Read our guide to Chicago’s starting-point locations for the full history of all three.
Countryside and William Tell Hotel
William Tell Hotel MOD Collection by Sonesta is located at 6201 Joliet Road in Countryside, along the community's historic Route 66 corridor.
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Willowbrook: Dell Rhea’s Chicken Basket
Dell Rhea’s Chicken Basket is a historic restaurant on the Route 66 corridor in Willowbrook, operating since the 1940s and listed on the National Register of Historic Places. Travelers interested in roadside dining can check its current menu, hours and operating information before visiting.
Joliet: Old Joliet Prison and the Rock and Roll Museum
Old Joliet Prison
Old Joliet Prison is a preserved historic site operated by the Joliet Area Historical Museum. Self-guided and specialty tours are available, and the site closes for the winter season. Check admission, closure dates and bag restrictions before arriving.
Illinois Rock and Roll Museum
The Illinois Rock and Roll Museum sits nearby and displays a large guitar-shaped sign. Confirm current details about the sign and museum access directly with the museum before including exact measurements in your plans.
Wilmington: The Gemini Giant
The Gemini Giant is a fiberglass “muffler man” statue located at the entrance to South Island Park, 201 Bridge Street, and is a public Route 66 photo stop. Check the City of Wilmington’s tourism page for current access information before visiting.
Dwight: Ambler’s Texaco Gas Station
Dwight is home to Ambler’s Texaco, a restored historic service station along the route. Visitor-center hours and seasonal access can vary — confirm current details before building it into your itinerary.
Pontiac: Route 66 Museum and Murals
Downtown Pontiac offers the Illinois Route 66 Hall of Fame and Museum, part of the Pontiac Museum Complex, along with a collection of outdoor murals and additional local museums. Build enough time into the itinerary to check museum hours and explore the murals on foot.
What to Check Before Your Illinois Route 66 Drive
- Decide which historic alignment or modern itinerary you plan to follow.
- Download or save a specialist Route 66 map before leaving.
- Check attraction hours and seasonal closures.
- Reserve ticketed tours in advance.
- Verify parking at Chicago and Joliet stops.
- Check accessibility directly with each attraction.
- Allow more time than ordinary navigation estimates show.
- Review road construction and closures on the day of travel.
- Choose a smaller number of priority stops rather than promising the entire route in one day.
- Confirm hotel and dining availability separately.
For turn-by-turn planning, consult a recognized Illinois Route 66 map or tourism guide rather than relying on this article for navigation.
Planning an Overnight Stop in Countryside?
William Tell Hotel MOD Collection by Sonesta is located at 6201 Joliet Road in Countryside. Its location can suit travelers exploring the suburban section of the historic corridor or continuing southwest through Illinois. Check current room availability, hotel policies and dining hours before building the property into your itinerary. Neighboring La Grange adds another easy stop—see our weekend guide to La Grange for downtown shopping, dining and historic walks.
Explore Rooms & Suites · Explore Tell’s Tavern · Read the history of William Tell Hotel
Planning around the centennial? See Route 66 Centennial events in Illinois. Have questions about your stay? Contact William Tell Hotel.
Frequently Asked Questions
What Route 66 attractions can I visit between Chicago and Pontiac?
Possible stops include Chicago’s Route 66 starting-point locations, Dell Rhea’s Chicken Basket, Old Joliet Prison, the Gemini Giant in Wilmington, Ambler’s Texaco in Dwight, and the Route 66 museum and murals in Pontiac. Opening hours and access vary, so check each attraction before traveling.
Where does Route 66 start in Chicago?
Travelers now encounter three relevant locations: the symbolic centennial start at Navy Pier, the familiar Begin sign near Adams Street and Michigan Avenue, and the original 1926 terminus near Jackson Boulevard and Michigan Avenue. Read our Chicago starting-point guide for the history of all three.
Can I visit Chicago, Joliet, Wilmington and Pontiac in one day?
Selected stops can be combined into a day trip, but visiting every museum, restaurant and landmark requires more time. Traffic, attraction hours and the historic alignment chosen will affect the schedule.
Is historic Route 66 a continuous modern highway?
No. Route 66 was removed from the United States Highway System, and its Illinois alignments changed over time. Travelers should use a current specialist map rather than relying on a single road number or ordinary navigation alone.
Where is the Gemini Giant now?
The City of Wilmington lists the Gemini Giant at the entrance to South Island Park, 201 Bridge Street. Check the city’s tourism page for current access information.
Is William Tell Hotel on Route 66?
William Tell Hotel is located at 6201 Joliet Road in Countryside, along the community’s historic Route 66 corridor. Travelers should consult a current alignment map when planning the exact route they want to drive.
Are Illinois Route 66 attractions open year-round?
Access varies. Public murals and outdoor landmarks may be viewable throughout the year, while museums, visitor centers and tour sites can have seasonal schedules, admission requirements or temporary closures.