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Traffic on the Kennedy Expressway in Chicago at sunset, looking toward the skyline.

The sign for the start of the historic route 66 highway in downtown Chicago

Vintage convertible car oldtimer driving through National Park USA on Route 66

Sign marking the beginning of historic Route 66 in Chicago with Sears Tower and other buildings in the background. Selective focus on the sign.

La Salle Street, Chicago, Illinois, USA

View of Chicago, IL Skyline from a pedestrian footbridge crossing Lake Shore Drive near North Avenue Beach in Summer

Ash Fork, Arizona, United States - September 22, 2023: 60s era Desoto Car on the roof of a building in Ash Fork, with Elvis driving.

Chicago Subway Loop in Downtown, Illinois

Chicago IL - USA: Colorful sign marking the beginning of Route 66 at Adams and Wabash, with lights

June 14, 2011 - Chicago, IL, USA: Sign in Chicago's Loop marking the beginning of historic Route 66

Vintage car oldtimer driving through National Park USA on Route 66

Historic Route 66 Shield Shaped Neon Sign Along the old route

Joplin, USA - May 10, 2019: Famous Route 66 mural with 1/2 car at the Route 66 in historic downtown Joplin, Missouri.

La Salle Street, Chicago, Illinois, USA

Route 66 beginning in Chicago roadsign

Route 66 Illinois Begin road sign at Chicago city downtown. Buildings facade background. Route 66, mother road, the classic historic roadtrip in USA

A selective focus shot of a road sign of the Route 66 in Illinois, United States of America

Map with close up of route 66

Sign announcing the begin of famous Route 66 in Chicago, Illinois.

Chicago, Illinois, USA. Sep 27, 2025. An iconic Route 66 sign, adorned with checkered flags, stands proudly in an urban setting, marking the historic beginning of the trail.

Lake Shore Drive in Chicago, Illinois, offers views of architectural icons, including the Willis Tower, completed in 1973.

Chicago, Illinois, USA

U.S.A. Illinois, Chicago, Adam street, the road sign of the Route 66 starting piont

Traffic moves along Interstate 90 south of downtown Chicago, Illinois.

Mural under a bypass on Route 66 in Oklahoma

A restored classic car cruising the freeways of Los Angeles.

Street, Downtown Chicago, Illinois, USA.

A black and white road sign of the historic Route 66 against blue sky.

Detail of a vintage car parked along the US route 66 neat the city of Galena, in the State of Kansas, USA.

Historic U.S. old Route 66 signs.

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