Festivals, Fairs & Special Events
Lawndale Route 66 Festival August 23, 2026
Lawndale Route 66 Festival: Where Cars and Culture Collide
Sunday, August 23, 2026 | 12:00–5:00 p.m.
Historic Ogden Avenue in North Lawndale (Central Park Avenue to Harding Avenue) | Free and Open to the Public
Get ready to celebrate 100 years of Route 66 on Chicago’s historic West Side!
The Lawndale Route 66 Festival brings the Mother Road to life with a high-energy celebration where cars, culture, music, family entertainment, and community come together. Taking place along historic Ogden Avenue—an original stretch of Route 66—the festival showcases North Lawndale’s unique place in the story of one of America’s most legendary highways.
Now in its second year as a full-fledged festival, the event has grown from Chicago’s longtime Historic Route 66 Classic Car Show into a vibrant community celebration featuring classic cars and motorcycles, live music and entertainment, the Jesse White Tumblers, the 40 Plus Double Dutch Crew, Broken Arrow Horseback Riding Club, The Firehouse Block Party, Sundays on The BLVD, The Young Doctors Club, The Great Lawndale Blood Drive powered by the American Red Cross, family activities, food vendors, youth programs, community organizations, and more.
Come experience the history, energy, and culture of Chicago’s Route 66 corridor as North Lawndale celebrates the Mother Road’s once-in-a-century milestone.
Where Cars and Culture Collide!
Admission: Free
