301 miles of Route 66 stretch through Illinois, the first (or last) of the eight states on your Mother Road journey. Starting at the Historic Route 66 Begin Sign in Chicago and ending at the Old Chain of Rocks Bridge that crosses the Mississippi River into St. Louis, Missouri, there are quintessential Illinois Route 66 attractions to see at every turn of the road.
You’ll find quirky roadside attractions, historical museums, vintage diners and drive-throughs, fun souvenir shops, and classic motels and hotels on this stretch of your road trip. You’ll even get to drive (or walk) on parts of the original road.
Looking for the best Illinois Route 66 attractions to add to your road trip itinerary? Use the filters below to search our Illinois directory by location, attraction type, or keyword to fill your travel plan, whether you’re spending a weekend in Springfield, taking a day trip from Chicago, or traversing all 301 miles of The Main Street of America across the state.
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Chicago Pizza Tour in Chicago, Illinois
Before taking off on your Route 66 adventure, explore one of Chicago's most famous commodities: pizza. A Chicago Pizza Tour will take you around the neighborhoods to taste some of the best pies the city has to offer. This bus-guided tour will take you to neighborhood favorites to sample all the best pizza in Chicago.
Walldog Murals in Atlanta, Illinois
In 2003 the Walldogs, an international organization of sign and mural artists, descended upon Atlanta, Illinois for a "Letter Rip on 66" gathering. Many of the Walldog murals are still in place today. Each year the Walldogs organization organized a festival where hundreds of artists visited a chosen small town to paint murals for three to five days.
3D Route 66 Shield Sculpture in Gardner, Illinois
Looking for one of the best selfie spots on Route 66? Stop at the 3D Route 66 Shield Sculpture in Gardner, Illinois. Find this roadside attraction in front of the Old National Bank in town. In anticipation of the Route 66 centennial celebration in 2026, many communities along the Main Street of America are coming together.
3D Route 66 Shield Sculpture in Dwight, Illinois
Get your pics on Route 66! Stop for road trip selfies at the 3D Route 66 Shield Sculpture in Dwight, Illinois. Find this roadside attraction in front of Ambler’s Texaco Gas Station. In anticipation of the Route 66 centennial celebration in 2026, many communities along the Main Street of America are coming together.
Must SeeHistoric Route 66 Begin Sign in Chicago, Illinois
Every great Route 66 road trip starts here: the Historic Route 66 Begin Sign in Chicago, Illinois. Established in 1926, Route 66, otherwise known as "The Mother Road," has long served as the ultimate path for anyone taking a great American road trip. Running from Chicago to Los Angeles the road spanned 2,448 miles.
