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Chicago: The Start of Route 66


Few Americans pay attention to a brown street sign on East Adams Street in downtown Chicago. If you are not looking for it, it is easy to ignore. But every few minutes a group of international tourists take a picture in the front of the sign. It reads, “Historic Route - Illinois U.S. 66 - Begin.”

Route 66 starting points on East Adams Street

Route 66 starting points on East Adams Street

The sign marks the modern-day starting point of an iconic American journey: the historic U.S. Route 66, the Main Street of America.

Chicago is the largest city in U.S. Midwest and the third-largest city in the country. It is more famous for its pizza, museums, and skyscrapers than its place in Route 66 history.

The 3,900-kilometer Route 66 links two of the biggest cities in the U.S.: Chicago, Illinois, in the east and Los Angeles, California, in the west.

For people traveling Route 66 today, Chicago offers big-city fun before beginning the drive through cornfields and small towns in Illinois. Before the Route 66 VOA crew headed west, we took in some of the sights, sounds and tastes Chicago has to offer.

Sights to see

If you like tall buildings and interesting architecture, Chicago is the city for you. Skyscrapers were born in Chicago. The first one went up in 1885 and was only about 33 meters tall.

Grant Park in Chicago

Grant Park in Chicago

One of the most famous skyscrapers in Chicago is the Willis Tower. The building is more commonly known by its original name, the Sears Tower. For years, it was the tallest building in the world. It remains one of the tallest buildings in the United States.

Completed in 1973, it has 103 stories, and stands 527 meters tall. Its observation deck provides amazing views of the city’s downtown and beyond.

Chicago’s downtown is called “The Loop.” Chicago’s train system, the L, circles this part of the city, giving the area its name. “L” stands for elevated. The train tracks run several meters above Chicago’s streets. The public transportation system is a Chicago icon. More than 700,000 people board the trains every weekday.

The Cloud Gate in Millennium Park

The Cloud Gate in Millennium Park

The Loop is also home to one of the largest outdoor sculptures in the world. British artist Anish Kapoor created the 10-ton sculpture, officially named “Cloud Gate.” The huge, metal, rounded object is often, and affectionately, called “The Bean.” It is a beloved “selfie” spot because photographers can see themselves in the mirror-like surface of the Bean.

One way to end a day of exploring Chicago’s museums, parks, and architecture is by eating at one of the city’s exceptional pizzerias.

A famous taste

Chicago-style pizza is very different than the pizza from other American cities.

It is more cheese than crust. Tomato sauce covers the top of the pizza. And it is truly more of a pie than a typical pizza. It is served in a deep round plate. In fact, Chicago’s pizza is called “deep-dish pizza.”

One of the first Chicago-style pizzerias opened in 1943. Two entrepreneurs opened Pizzeria Uno with the goal of creating a uniquely American version of pizza.

The history of just who created Chicago deep dish is a bit controversial. Some say the entrepreneurs themselves were the inventors. Others give credit to one very famous Chicago clan.

Lou Malnati was one of the original Pizzeria Uno cooks. He claimed that he came up with the Chicago deep dish pizza. He continued to work at Pizzeria Uno for many years without getting the credit he felt he deserved. But in 1971, he and his family took their pizza-baking skills and opened their own restaurant. Lou Malnati’s Pizzeria now has 35 locations throughout Chicago and its suburbs.

Chicago deep dish pizza

Chicago deep dish pizza

One of Lou Malnati’s downtown locations is a quick walk away from another Chicago institution: Jazz Showcase.

The sound of Chicago

If the windy city, as Chicago is known, had a soundtrack, the music would have to be jazz and blues. The city is famous for the all-American sounds. Jazz and blues clubs are scattered throughout the town.

Jazz Showcase is among the best of them. The historic club opened up in 1947. It is the oldest continuously operating jazz club in Chicago. Some of jazz’s greatest musicians have played there, including Count Basie and Art Blakey.

On our first night in Chicago, we visited Jazz Showcase. The club was intimate and low-lit. Pictures and murals of famous faces covered the walls. The crowd was warm and friendly, like most everyone in this Midwestern city.

Jazz Showcase, Chicago's oldest jazz club

Jazz Showcase, Chicago's oldest jazz club

The Ari Brown Quartet was performing a free show. The place was packed with jazz enthusiasts. At one point, the lead saxophonist brought up a jazz singer who happened to be in the audience. She shared the stage for a song and received huge applause.

Leaving the big city behind.

Chicago is not a typical Route 66 city. Aside from the official “start” and “end” signs, it can be difficult to find particular Route 66 sites in the city.

Our journey west began the next morning. We turned off of Michigan Avenue, Chicago’s most famous street, and onto East Adams.

Soon, the skyscrapers gave way to the open land and small towns that define Route 66.

I'm Ashley Thompson.

And I'm Caty Weaver. Join us next week for a report about international tourism along historic Route 66.

Do you like what you heard from Ashley and Caty? Leave a note in the comments section and on our Facebook page.

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Words in This Story

iconic - adj. widely known

exceptional - adj. unusually good; much better than average

controversial - adj. relating to or causing much debate, discussion or disagreement.

clan - n. (informal) a large family

institution - n. something that is very well known in a particular place.

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