Illinois is where it all begins, rising out of towering skyscrapers and the dirty waves of the south waters of Lake Michigan, wide eyes firmly set upon mysterious and inviting lands to the west - family vacations, natural wonders, better times. To be official, U.S. Highway 66 has two beginnings and two ends - its termini in Santa Monica and Chicago technically count for both - but since California was often the destination of the Mother Road traveler we are not alone in safely considering Chicago the highway’s origin. And while Route 66 is often portrayed as a dusty, crumbling, lonely road of primarily Southwestern influence, its trip through Illinois is a lovely demonstration of Midwestern hospitality and friendly family farms - not to mention some of the road's most interesting and historic landmarks.

Chicago to Saint Louis
What would eventually become U.S. Highway 66 in the Prairie State began in 1915 with the Pontiac Trail, a poorly constructed rut that wound from Chicago to Saint Louis via Joliet, Morris, Pontiac, Bloomington, Lincoln, Springfield, Carlinville, Edwardsville, Collinsville and East Saint Louis.  The trail was hardly sufficient for travel, especially compared to the superior Lincoln Highway that crossed the state west-to-east in the northern counties, and in 1918 the State of Illinois issued a series of bonds to construct a state highway system. The Good Roads movement had fostered nationwide interest in governmental road building after private construction had yielded an impractical, mostly unconnected series of poorly maintained trails, including the Pontiac Trail, and a year after the state of Wisconsin first adopted the practice of numbering its roads rather than assigning names Illinois followed suit. Primary highways, marked with lower numbers, were first constructed to travel longer, more important statewide routes between major cities, and Route 4 was no exception. Work soon began on Illinois 4, which shuttled traffic between Chicago and St. Louis along the former Pontiac trail.

Early construction of the road was simple, with laborers earning around forty cents/hour with horses dragging equipment along old trails close to the Chicago & Alton Railroad line.  Work started in 1922 and while by 1924 the road was “complete” it was still a mish-mash of tight curves and makeshift macadam surface that today would be considered barely navigable.  Work would not begin to better pave the road until after 1926.

The U.S. Highway System
It was in that year that the American Association of State Highway Officials, an organization comprised of the nation's state highway departments, laid out the first truly organized and official national system of highways, the U.S. Highway System. With automobile sales starting to boom in the middle of the prosperous 1920's, the goal was for the states to work together to expand the local road construction that had been growing in various states over the past decade into a well-planned, easily navigable system of solidly built highways that would ease nationwide, as well as regional, travel. The Federal Government had been working on funding state and local roads for a decade, offering up money for important corridors (specifically ones used by the U.S. Postal Service) but failing to help organize the improving highways. Subsequently AASHO (known today as AASHTO) took over, led by Oklahoma businessman Cyrus Avery, and while the group's U.S. Highway map was originally drawn as a grid, with routes running across the country in an orderly north-south and east-west fashion, Avery specifically wanted to bring traffic – and business – through his native Sooner State and drew U.S. Highway 60 as a diagonal path between Chicago and Los Angeles via St. Louis, Tulsa and the southwest.

There was immediate opposition to this proposed route, mostly from Kentucky and Virginia who felt the U.S. 60 designation should run from coast-to-coast as its number described...and, of course, it should be routed through their cities and small towns. A compromise was eventually proposed where Route 60 would instead begin in Springfield, MO and head toward the Atlantic, while Avery’s route would receive a lesser designation. Illinois and Missouri were anxious to get the route completed, so much so that the latter state had already began printing maps designating the route as US 60 to try to sway the decision their way. In the end, they were satisfied just to have a Chicago-to-Los Angeles route traveling through their cities no matter the number, the compromise was accepted, and a “lesser” number was decided on: sixty-six.

Construction & Promotion
On paper, Highway 66 would appear at a glance to be of no greater importance than many other coast-to-coast highways. In fact, two of the roads it would intersect in Saint Louis, Highways 40 and 50, could certainly claim a higher standing as corridors that truly stretched from the Atlantic to the Pacific, passing through more and larger metropolitan areas than the diagonal, rural Route 66. But AASHO President Avery would not stand by and have his highway take a backseat to any other road, and with the formation of the Route 66 Association of America he set out to promote Route 66 and ensure it would be the first road to be finished and also the most promoted new highway in the country. Advertisements encouraging motorists to drive the highway were taken out in newspapers and magazines nationwide, especially in 1932 as Americans shuttled to Los Angeles for the Summer Olympic Games. In 1927, the annual California-to-New York nationwide footrace known as the "Bunion Derby" was held along the newly birthed Route 66, and small towns in all eight states waited for the pack of athletes to sprint through their downtowns on the way east. Newspapers throughout the country carried accounts of the race each day, giving more press to Avery's pet project.

Also helping the cause was the willingness of each state along the route to devote its primary road construction resources to the Mother Road. Illinois' desire to put Route 66 first was rooted in the new highway's path through what was arguably the state's most important transportation corridor and the need to better pave it. At this point Saint Louis was still one of the largest cities in the nation, not yet having been hit with the drop in population that loss of industry and white flight would inflict upon it at the dawn of the Interstate age, and having a good road between this transportation hub and the second-largest city in the nation was paramount. It did not hurt that this stretch would also flow traffic into the state's capital city, Springfield, as well as past Illinois State (Normal) University in the twin cities of Bloomington-Normal. Other primary routes in the state were forced to take a backseat as the state made sure Route 66 was ready first; US 40 and 50 were shorter west-east routes that passed through few major Illinois communities outside of the Metro East, and US 51, as many miles as it would trod on through Prairie State, saw no metropolis larger than Rockford. As important as these highways may have been to the overall structure of the U.S. Highway System and to regional out-of-state transportation, they mattered far less to residents of Illinois and thus the attention of the Land of Lincoln was set squarely upon Route 66.

Along with California, Illinois was one of the first states to pave Route 66 from border to border, but work was never truly complete. Over the years the highway's path changed constantly, finding new, larger stretches of pavement and bypassing towns as they grew larger and slower, benefiting from the traffic the road provided them and then abruptly took back. Read more about the various paths the Mother Road took from Chicago to Saint Louis in the next section: Alignments and Bypasses or: How I Learned to Stop Worrying and Love The Plainfield Alignment.