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100 years of Route 66: itinerary to discover the original route from Chicago to Cicero. An exciting journey through history, art, culture, traditions and civil rights.
100 years of Route 66: on the trail of the original route in Chicago
“Get your kicks on Route 66”, first sang Nat King Cole with the King Cole Trio in 1946.
A global success that helped immortalize the Main Street of America that connected the most remote areas of the country with two of the most crowded and vital cities, Chicago and Los Angeles.
The road that even earlier Steinbeck in his novel “The Grapes of Wrath”, Pulitzer Prize winner in 1940, had defined as Mother Road of America. The road of flight!
“66 is the path of people in flight, refugees from dust and shrinking land.
From the thunder of tractors and shrinking ownership.
From the desert’s slow northward invasion, from the twisting winds that howl up out of Texas.
From the floods that bring no richness to the land and steal what little richness is there.
From all of this, people are in flight, and they come into 66 from the tributary side roads.
From the wagon tracks and the rutted country roads.
66 is the mother road, the road of flight”
(Steinbeck, The Grapes of Wrath)
Inaugurated on November 11, 1926, and completely finished in 1938, Route 66took the men and women of the Great Depression first and then of the Dust Bowl towards the search for a better future on the Californian Golden Coast.
A route through 8 states, Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California and 3940 km of travel.
From the end of the 40s, it became also fueled by the literature of the Beat Generation and the themed filmography of the ’50s and ’60s, the undisputed symbol of freedom in all its forms for generations of restless young people and for families in search of fortune.
It was originally intended to be Route 60, to follow road identification used to facilitate traveler orientation. The roads from east to west had to have even numbers, those from north to south odd-numbered. But due to a dispute by the state of Kansas, which wanted 60 to be assigned to another route, it eventually became Route 66.
A myth that survives, despite the dark years in which the Mother Road literally risked disappearing from American road maps due to the construction of new and faster interstates. It still fascinates and attracts many travelers today.
On November 11, 2026, America will celebrate 100 years of Route 66.
What better opportunity to rediscover the most significant, even though lesser-known stories, places and routes, in addition to its most iconic features and attractions that we all know by now?
And why not start right from Chicago to Cicero, the original starting point of Mother Road on the old SP14?
100 years of Route 66: on the trail of the original route in Chicago
Route 66 in Chicago isn’t just an iconic sign marking its beginning, the sign of a famous diner where you can have breakfast before leaving or the road taking you straight out of town, as many think.
(Old) Route 66 in Chicago is the history of the States, abolitionism, immigration from all over the world, and civil rights.
100 years of Route 66: on the trail of the original route in Chicago
From Cicero, the first real starting point of Mother Road until 1930, when it was understood that to give greater prestige to the Main Street of America it would be necessary to give it a more iconic and recognizable starting point. And the magnificent Chicago was only 14 km away.
From Senator Douglas, the first great supporter of transcontinental travel. To the abolitionist Reverend Frederick Douglass, to whom the same park on Old Route 66, Douglas Park, was dedicated over time, which later became Douglass (Anna and Frederick) Park.
From Martin Luther King, who in 1966 lived with his family in North Lawndale, right along the first km of Old Route 66, in one of the most difficult years of his non-violent protest, up to the fearsome Black Panther Party which met in a nearby church.
100 years of Route 66: on the trail of the original route in Chicago
From the immigrants from around the world who contributed to making this country great. To the Latin and African American communities, even Italian ones. From Little Village to Lawndale.
From the first activities, diners and attractions that stimulated the stop. And that from Cicero – even before Chicago – united America on a road that represented dreams, hopes, sometimes even illusions, and of course the expectations of its travelers.
100 years of Route 66: on the trail of the original route in Chicago
Therefore, not always just a myth of freedom and infinite landscapes, as many people like to talk about Route 66 today
Often a symbol of redemption, suffering and determination.
And a mix of stories – more or less well-known – and characters – more or less famous – whose narration continues to open a privileged window of observation on the most genuine, hard and fascinating essence of the truest, most complex and varied America.
100 years of Route 66: on the trail of the original route in Chicago
To celebrate 100 years of Route 66, the tourism board of Choose Chicago in collaboration with local street artist Ben Marasco has created an iconic tribute mural at Mother Road.
You can find it on the outside wall of Lulu’s Hot Dogs, another unmissable stop on Old Route 66.
The mural is on West Taylor Street, just across from Ferrara Bakery.
100 years of Route 66 in Chicago: Ben Marasco’s Mural
Here you will find the map published by Choose Chicago with most of the stops indicated along the original route of Old Route 66 in Chicago.
From the official sign marking the start of Route 66 along Michigan Ave, passing The Berghoff Restaurant and historic Lou Mitchell’s.
And again, Lulu’s Hot Dogs, Ferrara Bakery, La Catedral Cafe, Douglass Park, Martin Luther King Legacy Apartments, and the iconic (now decommissioned) Castle Car Wash.
As far as reaching Cicero.
100 years of Route 66: on the trail of the original route in Chicago
To best organize your visit to all the locations I invite you to contact Tours with Mike.
So, you will be able to experience and personalize your discovery of Old Route 66 in Chicago in the best possible way and with a respectable playlist!
Experience carried out and article created in collaboration with IPW, Choose Chicago & Tours with Mike, during IPW 2025 Chicago.
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