Route 66 in Chicago

In the course of my historical research of Route 66 and its evolution in Chicago, I acquired a large collection of postcards, vintage photographs, maps, and periodical images that stand as witness to Chicago's highway history. In Route 66 in Chicago these artifacts are brought to life as we explore the connections between the Windy City and the Mother Road.

Route 66 in Chicago explores the changing look of Route 66's starting point at Chicago's "route center" intersection of Jackson Boulevard and Michigan Avenue, which was once considered one of the busiest crossroads in the nation. Vintage and modern images show the connection between 66 and Chicago's transportation past of waterways, native American footpaths, and transcontinental railroads. Symbols of Chicago's financial wealth are shown to interpret the flow of commerce between the city and its transportation corridor hinterland through downstate Illinois and beyond. We look at the dining, lodging, and entertainment businesses that grew along the 66 corridor to serve Chicago's visitors. Finally, we examine the devastation caused by the coming of the interstates, which siphoned through traffic away from the 66 corridor, and we look forward with hope that the remaining 66 legacy will help in the corridor's economic uplift.

Click HERE for more information on Route 66 in Chicago

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Exploring Route 66 in Chicagoland

As towns along the Route 66 corridor from Tulsa to Albuquerque and from Odell to Barstow have found ways to preserve and celebrate their highway history, Chicago, where the road BEGINS, has done next to nothing to develop its Route 66 heritage. This often leaves visitors frustrated at the very beginning of their "California trip." With Exploring Route 66 in Chicagoland, the tourist can finally learn the history that shaped U.S. 66 in the Windy City and in all of Cook County.

Whether you are an armchair tourist, taking a "virtual tour" through the written word; whether you are driving through Chicago, wishing to have a better understanding about the historical context of the sights along the highway; or whether you are wishing to explore the Route 66 corridor in Chicago's Loop on foot...

Exploring Route 66 in Chicagoland will help you get the most out of your adventure. So, settle into your recliner, fasten your seat belt, or tighten your shoelaces--no matter how you take the journey, it starts HERE, my fellow Road Warriors, in a city named Chicago!

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Postcards and Photographic Prints of Chicago's Route 66

Click here to look at the choices and learn more about the available Postcards and Prints showing the Chicago skyline in the Route 66 corridor, Lou Mitchell's Restaurant, the Castle Car Wash, and more!

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Tours! Tours! Tours!

The Windy City Road Warrior has spent much of the last 5 years researching the history of Chicago, its highways, and the sites seen along the way. NEW for 2008, we are partnering with Windy City Connection to offer all day Motor Coach excursions from Chicago to Wilmington. We also offer 2-hour walking tours of sections of Chicago's Loop, as well as personally narrated driving tours of US 66 through Chicago and its nearby suburbs. Tours of US 32/34 and US 41 also available. For more information, Click Here!

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Postmarked Commemorative Cover

The official Route 66 signs came down at the Eastern Terminus of Route 66 in January of 1977. This postmarked cover commemorates the 25th anniversary of this event, when the 66 shield was briefly displayed again! Click here to purchase!

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