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April 7, 2026

What to Do on Route 66 in Chicago

City Cast Chicago

What to Do on Route 66 in Chicago

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In April 1926, Route 66 received its iconic number. The so-called Mother Road takes you all the way to California, but it begins in Chicago. (Now at Navy Pier!) In celebration of 100 years, we’re revisiting our little road trip from last year. Host Jacoby Cochran hopped in the car with Dario Durham and Sara Faddah, hosts of 77 Flavors, to drive the Chicago leg of old Route 66. Along the way, they pointed out favorite attractions, spots to eat, and saw the city from a new perspective.

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