Route 66, arguably the most famous highway in America, has a start and end point in Chicago. But the Mother Road isn’t as big of a deal here as it is in other towns along the 2,448-mile highway. Tour guide Mike McMains says that’s because Chicago just has a lot of stuff going on.
But in collaboration with the state and city ahead of the route’s centennial in 2026, McMains’ new trolley tour is showing locals notable spots along the Chicago leg of the route, which stretches west from downtown.
Shots from Mike McMains’ Route 66 tour — including a surprise run-in with historian Shermann “Dilla” Thomas. (Courtesy of Mike McMains)
Something to Eat
You can get jerk spices from Jerky Jerk, sandwiches and pasta from Ferrara Bakery, and hot dogs from Lulu’s all on Taylor Street. Lou Mitchell’s is older than the highway itself. La Catedral, which has locations in Little Village and North Lawndale, touts itself as home to the world’s best chilaquiles.
Something to See
Visit where Martin Luther King Jr.’s West Side apartment once stood. The civil rights activist lived in the city in the late '60s to protest unfair housing practices. Then, check out an antique car show outside of La Catedral in North Lawndale Saturday and Sunday. Anyone can catch it — not just folks on the tour.
Something to Do
The Epiphany Center for the Arts is a former church and Black Panther gathering spot that has been turned into an arts center with exhibits and concerts. Pop into the Art Institute for a self-guided tour of items from Route 66 states.
The Chicagoland section of Route 66. (U.S. Department of Transportation)
The last weekend of tours is here. Check online to see if tickets are available. Alternatively, you can wait in the bus loading zone and claim a no-show ticket.
Don’t sleep on McMains’ other unique tours from Chicago’s ugly buildings to underground rats. He has an upcoming Illinois presidents tour ahead of the Democratic National Convention and election.
