1622 W Jackson Blvd, Chicago. This hotel which is still open, now as the "Hotel Chicago" used to be the Rosemoor Hotel , which as listed...

1676 W Ogden Ave. Chicago. The photograph below in its credits tells us that this was a "Typical Standard Oil gas station" of the 1970s,...

Built in 1856 Drive west along Adams St. On the NW corner with S Desplaines St (700 W Adams) is the oldest standing church in Chicago ,...

One block past the river, to your left is  Chicago's   Union Station , the railway depot. Ho inside to take a peek at its Beaux-Arts...

Cross the Chicago River's South Branch using the Original Route 66 Bridge that carried Route 66, built in 1927 and rehabilitated in 1996,...

Continue westwards passing under the Elevated Railroad at Wells St. On the next block, at S. Franklin St. (233 South Wacker Drive) is the...

Now the "W" Hotel....Head west, after crossing La Salle St., to your right is the former Midland Hotel, now the "W Hotel" at 172 W Adams,...

Centennial Marker Sign Where Route 66 Begins In 2024, the Chicago Tourism Office launched a campaign to honor Route 66 ahead of ahead of...

111 South Michigan Avenue. With a large collection of Impressionist paintings it also has a Route 66 Exhibit.

At the Park's northern tip, stands "Cloud Gate;" a giant mirror-like stainless steel, curved sculpture by Anish Kapoor, also known as "...

1400 South Lake Shore Drive. A must-visit Natural History Museum, it holds "Sue" the World's largest T-Rex "Sue", Egyptian mummies and...

1200 South Lake Shore Drive. The world's largest indoor aquarium, with over 20,000 animals.

Adler Planetarium 1300 South Lakeshore Drive. It is America's first planetarium, built in 1930 on what was then an artificial island on...

Listed in the National Register of Historic Places This is the Eastern Terminus of Route 66. Here was the "End of Route 66 sign" where...

Listed in the National Register of Historic Places Grant Park is.... Grant Park the Eastern Terminus of Route 66. Here was the "End of...

But as we said before, Route 66 also "Ended" in Chicago, for those driving eastwards. The "End" sign is there too, one block south of the...

The sign is located at 99 E Adam St. (NW corner with Michigan Ave.), another s ign is on the south side of the street, halfway down the...

The 1992 "Route 66 Law" or "U.S. Route 66 Designation Act" designated the existing portion of Route 66 in Illinois as a State historic...

Route 66 shield being removed, Jan 1977, Chicago. Source . Click image to enlarge The signs were all removed when U.S. 66 was decertified...

Route 66 was created in 1926 to link Chicago with Los Angeles, and unlike the Interstate highways whose exits are numbered from west to...