Cross the Chicago River's South Branch using the Original Route 66 Bridge that carried Route 66, built in 1927 and rehabilitated in 1996, it is a Double Trunnion Bascule Deck Truss (Status: Open to traffic). The Chicago River runs through Chicago, including its central downtown district. Over the centuries it evolved into a system of rivers and canals (now 156 miles or 251 km long). It's flow was reversed and now instead of discharging into Lake Michigan, it flows westwards into the Mississippi River through the Des Plaines and Illinois Rivers. The first bridge across it was built in 1832, and it peaked at 52 bridges in the 20th century. Now 38 remain, all of them different types of movable bridges. 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 style facades with Corinthian columns, its lavish bronze lamps and the vast Hall. Taken from www theroute-66.com

Continue westwards passing under the Elevated Railroad at Wells St. On the next block, at S. Franklin St. (233 South Wacker Drive) is the former Sears Tower; the tallest skyscraper on Route 66. black building tall slender, with different box shaped structures supporting it Sears Tower, Chicago, Il. Source Now named "Willis Tower", but best known as the Sears Tower; it is a 110-story building. It is 1,450 feet high (442 m) and when it was finished back in 1973 it became the tallest building in the world (overtaking the Twin Towers of the World Trade Center in New York). It eventually lost its title; and now after the completion of the New World Trade Center building in NYC in 2014, it is the second tallest building in the US and the Western Hemisphere and the 16th on a global scale. It was the work of architect Fazlur Rahman Khan, and is now named after Willis Group, who lease space in the skyscraper. More than one million people visit its "Skydeck" observation deck each year: on the 103rd floor, 1,353 feet up in the air, with stunning vistas of Chicago and four states; you can see up to a distance of 50 miles (80 km). Info from www.theroute-66.com

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, Chicago Now it is a luxury Starwood Hotel, the "W Chicago City Center Hotel" and its facade remained untouched. The businessmen club named the Midland Club commissioned architect V. H. Vitzthun to build an Art Deco styled skyscraper. The tower combined offices and the club. But, the Crash of 1929 and the Great Depression that ensued upset the plan, most of the building's office space remained vacant. So in the mid 1930s, the club leased some of it to the Midland Hotel which ended up buying the building in the 1940s. Info taken from www.theroute-66.com

The Berghoff Restaurant opened in 1898, after Herman Berghoff”s beer stand at the 1893 World’s Fair became very popular. It first offered free sandwiches with the purchase of a nickel beer. During prohibition, it became known for its authentic German food. When Prohibition was lifted, Herman was able to procure the city’s first ever liquor license, opening up The Berghoff Bar while still running the restaurant. The building is located at 17 W. Adams St. which is on Route 66. Not only was it a popular establishment for locals, but it was also a favorite destination for Route 66 travelers. Continue walking west along Adams, one block west is the famous German Restaurant, Berghoff's. Don't miss its neon sign. black and white, 1930s, people walking sidewalk, truck with meat sign reads PRIZE BEEF, for the Berghoff restaurant, seen behind it 17 West Adams. This restaurant has been owned and operated by the Berghoff family since it opened back in 1898. Herman Berghoff emigrated from Germany to America in 1870, and among other things, he opened his own beer brewery in Indiana. He moved to Chicago in 1893 to sell his beer at the Chicago World Fair, and it went so well that he moved here to W Adams St. in 1898. Berghoff neon sign and beyond to the right the "Sears" Tower in Chicago, Illinois

Centennial Marker Sign Where Route 66 Begins In 2024, the Chicago Tourism Office launched a campaign to honor Route 66 ahead of ahead of the Route 66 Centennial (1926-2026) . You can find one here across from the Art Institute, by the Orchestra Hall, at the beginning of Route 66. There are other signs along Ogden Avenue at 1969 W. Ogden, 3100 W. Ogden and 3801 W. Ogden. As you turn the corner from Michigan into E Adams St. on the north side of the street is the famous BEGIN Historic Illinois US 66 brown and white road-sign shield on a light post, there is second one on the south side of Adams, half way down the block, to your left. We have already described these road-signs further up in our Route 66 'Begin' Sign section. Historic Route 66 Marker Sign On the corner, to your left ( SE corner here) of Wabash and Adams is a formal Route 66 "Begins" marker sign (street view), pictured. With a U.S. 66 shield superimposed on a map of the Chicago area. Here, running above Wabash is the the elevated railroad known as The Chicago "L" (short for "elevated") which dates back to the 1890s.

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 " The Bean ", it was built between 2004 and 2006.

1400 South Lake Shore Drive. A must-visit Natural History Museum, it holds "Sue" the World's largest T-Rex "Sue", Egyptian mummies and more! Like the The Route 66 Benld Meteor  that fell in 1938 in Benld on the 1926 US 66 alignment.

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 Lake Michigan.

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 East Jackson Blvd. met US 41, by the shore of Lake Michigan. It dates back to 1844 when it was created as Lake Park. In 1901 it was renamed after US President Ulysses S. Grant, and grew to its present size (319 acres or 1290 ha) through land reclamation projects. It lies east of the built up area on Michigan Blvd. When the railroad was built along the shore of Lake Michigan, a lagoon was formed which was filled in to extend the park, which continued into the 20th century. It is bound by Randolph Dr. and the Chicago River on the north, Lake Michigan on the east, Michigan Ave on the west and McFetridge Dr. on the south. Open from 9 AM in the morning daily. Info taken from www.theroute-66.com