What to Do on Route 66 in Chicago

This episode of CityCast Chicago celebrates the 100th anniversary of Route 66, exploring its historical significance and modern-day presence in the city. Host Jacoby Cochran, joined by 77 Flavors of Chicago’s Sarah Fata and Dario Durham, begins at the official starting point of Route 66—Michigan and Adams in downtown Chicago—highlighting the Art Institute, historic signage, and the cultural evolution of the route. The journey follows Old Route 66 through Ogden Avenue, passing through diverse neighborhoods like Greektown, the medical district, Douglas Park, and the Chicago Botanic Garden’s farm on Ogden. Along the way, the hosts spotlight local eateries, public art, historic landmarks, and institutions such as the Chicago Cubs’ original West Side ballpark, the Illinois Medical District, and Cinespace Studios. Despite Route 66’s decline as a major interstate, the episode emphasizes its enduring legacy in Chicago as a cultural connector, revealing how a short drive reveals the city’s layered identity, from wealth to community, history to innovation. The hosts reflect on how the route, though now largely urban and unglamorous, still offers a unique lens into Chicago’s geography and soul. Key takeaways include: Route 66’s Chicago start is symbolic, not scenic; the route reveals hidden layers of the city’s neighborhoods and institutions; the Illinois Medical District is the largest in North America and a major historical hub; the 100th anniversary celebration has shifted the official start to Navy Pier; and even a short drive on Route 66 can feel like a full-day adventure through Chicago’s diversity. The episode also underscores the importance of paying attention to the details—signs, murals, architecture—that make the journey meaningful.