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A mural-in-progress about Route 66 lies on the ground as attendees visit booths during the Douglass Juneteenth Celebration at the Douglass Park Cultural and Community Center Saturday, June 6, 2026, in Chicago. (John J. Kim/Chicago Tribune)
A mural-in-progress about Route 66 lies on the ground as attendees visit booths during the Douglass Juneteenth Celebration at the Douglass Park Cultural and Community Center Saturday, June 6, 2026, in Chicago. (John J. Kim/Chicago Tribune)
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A season of Juneteenth celebrations in Chicago kicked off at Douglass Park Saturday afternoon with enthusiastic speeches, music, food and fanfare.

For more reasons than just the abnormally early date, Saturday’s weeks-early Juneteenth celebration was not standard. North Lawndale neighbors celebrated both the upcoming Juneteenth holiday, which recognizes the emancipation of American slaves and the centennial of historic Route 66.

Jonathan Kelley, 54, of the community museum Lawndale Pop-up Spot, worked with Ahdohny Routheni, 38, of Juneteenth Renaissance Institute to put on Saturday’s small event.

“This [Juneteenth Celebration] is unique and special because of the intentional connection with Route 66,” Kelley said. “For North Lawndale, the centennial of Route 66 is pretty important because of the history of Ogden Avenue, its importance for this neighborhood both economically and culturally as an area of moving. We wanted to really embrace that.”

Historic Route 66 connected Chicago to Santa Monica, California. The thoroughfare played an integral role in The Great Migration, when millions of Black Americans moved from the Southeastern United States to the Midwest and West in search of better socioeconomic opportunities, according to the Chicago Public Library.

“This is where Route 66 began, in the heart of the west side. This is also where Martin Luther King’s Poor People’s Campaign began,” Routheni said. “This is the road that made cities or broke families. When you had displaced Native Americans and misplaced Black people of slavery descent, Route 66 represented the dream of America.”

Neighbors were able to enjoy a tram ride on Ogden Avenue to learn more about the local history with the North Lawndale Historical and Cultural Society. Beyond the drive, attendees enjoyed music, food, crafts, poetry reading and dance performances.

The celebration is among the first to happen in Chicagoland. There are plenty more free festivities to happen throughout the metro area in celebration of Juneteenth. Here are just a few happening in the area.

Upcoming Chicago Juneteenth festivals:

Juneteenth Wellness 5K | June 14, 7:30 a.m.-noon, Garfield Park Football Field, 138 S. Hamlin Blvd., West Garfield Park

2nd Annual Lineage & Legacy Juneteenth Jubilee | June 19, 4445 S. King Drive,, Grand Boulevard

1865 Fest | June 19 and June 20, noon-8 p.m., Garfield Park Music Court Circle, 100 S. Woodward Drive, Garfield Park

Bronzeville’s 6th Annual Juneteenth Celebration | June 20, 10 a.m.-3 p.m., 3701 S. King Drive, Douglas

12th Annual Chicago Juneteenth Parade | June 20, 11 a.m., 2901 W. Monroe Street, Garfield Park

Boxing out Negativity Juneteenth Celebration | June 19, 3-7 p.m., 1616 South Avers Avenue, North Lawndale

Juneteenth Celebration | June 14, 11:30 a.m.-1:30 p.m., 405 North Euclid Avenue, Oak Park

The 7th Annual Beverly/Morgan Park Juneteenth Family Festival | June 20, noon-7 p.m., Intersection of  W. 110th Street  and  S. Longwood Drive, Morgan Park