Kick Off Your 66 Road Trip At New Starting Point Sign

Beginning in downtown Chicago and stretching more than 2,400 miles to the Pacific Coast, Route 66 has shaped the history of the United States, remaining a major attraction for both national and international visitors. In preparation for the Route 66 Centennial Celebration in 2026, Choose Chicago has installed new signage at the official Mother Road starting point and in three Chicago neighborhoods along Route 66, aiming to draw visitors to these locations and surrounding businesses while providing educational experiences.

“Originating at Jackson Boulevard and Michigan Avenue, Route 66 is one of the most important and historic westbound arteries connecting America to the heart of the country – Chicago. We are proud of its history and profound impact on our city,” said Rich Gamble, interim president and CEO of Choose Chicago. “With these new initiatives, we are refreshing our relationship with the ‘Mother Road’ and ensuring that visitors from all over the world can experience the magic of Route 66 throughout Chicago.”

You’ll find the four new signs located at:

Starting Point Pylon: 122 S. Michigan Ave. (South Michigan Avenue and East Adams Street)

Tri-Taylor Interpretive Sign: 1969 W. Ogden Ave. (West Ogden and South Damen avenues)

Douglass Park Interpretive Sign: 3100 W. Ogden Ave. (West Ogden and South Albany avenues)

North Lawndale Interpretive Sign: 3801 W. Ogden Ave. (West Ogden and South Hamlin avenues)

“The history of Route 66 is fundamental to who we are as a state and our appeal as a global destination,” said Daniel Thomas, deputy director of the Illinois Department of Commerce and Economic Opportunity, Office of Tourism. “As we prepare for the centennial celebration of Route 66, we are delighted to support these new programs, and we invite visitors to explore all of the Route 66 programming in Chicago and throughout Illinois.”

The new Route 66 starting point pylon, conveniently located on Michigan Avenue across from The Art Institute, features a large tricolor Route 66 shield – a great photo op to commemorate the start of your trip. Here’s a look at some of the other can’t-miss photo-op shields you’ll find between Chicago and Pontiac, Illinois, along The First Hundred Miles.

3D Route 66 Shield Sculptures

Multiple locations along The First Hundred Miles

One of the most exciting new photo-op hunts you’ll find along the modern Mother Road is Heritage Corridor Destinations’ newly added 3D Route 66 Shield Sculptures. These enormous 3D metal sculptures have been placed in popular Route 66 towns running from Chicago to Pontiac, creating a massive chain of selfie spots celebrating The First Hundred Miles.

Locations include: Burr Ridge (15W400 Harvester Drive), Lockport (1327 S. State St.), Romeoville (55 Phelps Ave.), Joliet (204 N. Ottawa St.), Dwight (W. Waupansie St.), Gardner (128 Depot St.) and Pontiac (near Livingston County Courthouse).

World’s Largest Route 66 Shield

100 W. Howard St., Pontiac

Dubbed the “Quintessential Route 66 Photo Op,” this outdoor mural is known as the largest Route 66 Shield in the world, aptly painted on the back of the Route 66 Museum in Pontiac. Created by Diaz Sign Art in 2007, the signage has become a huge tourist attraction in its own right, and is an extremely popular photo op for visitors and Route 66 travelers. You even can submit your photo at IL66assoc.org to join a growing archive of people who have stopped at the iconic modern mural.

To explore more photo ops along Route 66, head to TheFirstHundredMiles.com and follow Route 66 - Illinois on Facebook.