The “Begin Route 66” sign
The road officially starts on Adams Street just west of Michigan Avenue, across from the Art Institute.
Look it up ›Drive Route 66 from Chicago to Santa Monica, about 2,400 miles. The road turns 100 on November 11, 2026.
The road begins a block from Lake Michigan, runs out through Chicago’s suburbs, then straight across flat corn and soybean country to the Mississippi.
The road officially starts on Adams Street just west of Michigan Avenue, across from the Art Institute.
Look it up ›Breakfast diner open since 1923. People waiting in line get free doughnut holes, and some get a box of Milk Duds.
Look it up ›Fried chicken served since 1946 in a former gas station lunch counter, and run by the Rhea family since 1963.
Look it up ›A 28-foot fiberglass astronaut holding a rocket, put up in 1965 outside the Launching Pad drive-in.
Look it up ›A free Route 66 museum and more than twenty murals painted on downtown buildings.
Look it up ›The Funk family has made and sold maple syrup here since the 1890s, and still spells it “sirup.”
Look it up ›A 19-foot giant holding an oversized hot dog, moved here from a Cicero restaurant in 2003.
Look it up ›The only house Abraham Lincoln ever owned, a few blocks off the old route. His tomb is nearby in Oak Ridge Cemetery.
Look it up ›Ed Waldmire started selling his cornmeal-battered hot dog on a stick here in 1946. The family still runs it.
Look it up ›Opened in 1924 and in this building since 1935, one of the oldest restaurants on the whole route.
Look it up ›A mile-long 1929 bridge over the Mississippi with a 22-degree bend in the middle. Now open only to walkers and bikes.
Look it up ›