(Above) Route 66 marker near Michigan and Adams in the Loop (Adobe Stock).

By Steven Dahlman

16-Feb-26 – Perhaps feeling a bit of wanderlust, U.S. Route 66 is relocating its starting point.

The Chicago City Council has officially designated Navy Pier as the new eastern terminus of the iconic highway, which stretches 2,448 miles through eight states to the Santa Monica Pier in California. The resolution, introduced on February 11 by 42nd Ward Alderman Brendan Reilly, arrives as the city prepares for the highway’s centennial in 2026.

(Left) People and boats wait for a Chicago Air and Water Show near the northeast corner of Navy Pier.

“Route 66 has always been about dreams and possibility,” Reilly said. “Designating Navy Pier as the eastern terminus honors Chicago’s historic role while creating a powerful pier-to-pier connection that captures the true spirit of the American journey.”

Dubbed “The Mother Road” in John Steinbeck’s 1939 novel, The Grapes of Wrath, Route 66 served as a primary artery for those migrating west during the Dust Bowl. As one of the original U.S. Highways, it sustained local economies for decades before being bypassed by the Interstate Highway System in the 1960s and 1970s. Though officially decommissioned in 1985, the road saw a resurgence in the late 1980s through “Historic Route 66” designations and federal grants in 1999 aimed at preserving its iconic features.

The original starting point was the intersection of Michigan Avenue and Jackson Boulevard. In 1933, it moved to Lake Shore Drive before shifting in 1955 to Adams Street, less than a block from Michigan Avenue.

The western endpoint has a history of movement as well; it was relocated one mile west to the Santa Monica Pier in 2009.

(Right) Route 66 “End of the Trail” sign at Santa Monica Pier. Photo by Andy Konieczny.

A new Route 66 sign will be unveiled at Navy Pier on March 25, 2026. The day-long celebration will include the 28th Annual Worldwide Toast to Harry Caray at Harry Caray’s Tavern. The legendary broadcaster grew up in St. Louis and famously traveled Route 66 to reach Wrigley Field for his first announcing job.

The celebration will also feature live music by Tom Higgenson of the Plain White T’s, classic car displays from the Volo Auto Museum, and appearances by Chicago White Sox legend Ron Kittle and Chicago Cubs legend Ryan Dempster.