Route 66: Leaving Chicago

I wanted a convertible—

—a  red vintage convertible with shiny chrome rims and white leather seats. But the Enterprise at O’Hare didn’t have any of those.

“You wanna Impala?” The guy asked, but it was white—and I’m allergic to renting white cars. One day on the road and white cars start looking like dirty underwear.

I futzed around the lot, disappointed. If I couldn’t motor down Route 66 in something vintage and cool, I needed to at least roll in something American. I passed over the BMW’s and then salivated over the midnight-black Mustangs (“You’re not authorized to upgrade”).

“Do you have any Camaros?” I wondered.

Instead, I left the airport in a charcoal Chevy Malibu—a car that I liked for its extra legroom and the successful connection of my iPod. Would you rather drive across country in a glossy antique with scratchy AM radio—or would you rather spend a month with a set of practical wheels and Sirius XM?

Though I can imagine the collective face palm of thousands of car aficionados as they read this, I must explain that I know ridiculously little about cars and that I chose my ride solely for its name—Malibu. I am headed to California on Route 66, after all, so it seemed fitting. (This is NOT an endorsement—we’ll revisit after my 2,400-mile test drive.)

Navigating Chicago’s crazy yarn ball of roadways left me feeling like a mouse on a twig in the rapids. All I cared about what not drowning (or crashing) into the throngs of Illinois drivers who feel like turn signals are for losers. Like some great rip tide, Chicago’s freeway sucked me into the city and then spit me out miles away from where I wanted to be—the starting line of Route 66.

Instead, I found myself parked at North Avenue Beach, the hum of Chicago behind me, and the endless azure of Lake Michigan quieting my eyes.

There’s this Ukrainian superstition that I picked up—how before embarking on a long journey, a traveler should sit down and wait for a spell. It’s common sense, really, but it’s become my own tradition before any big trip.

And so I sat on Chicago’s beach and watched the lake. Truly, there is no blue like the blue of Lake Michigan. It is the blue of Navajo turquoise and Norwegian glaciers and that Kool-Aid color you never buy. It is a calming color, and after my frenetic trip from the airport, I was glad for some quiet time by the lake. Above me, a squiggle of white cloud showed off the intensity of the royal sky. A lone fisherman pulled on his line.

I took off my shoes and sunk my toes into the skin-colored sand of the beach, inhaling when the cold waves splashed up to my ankles. Then I filled up a bottle with Lake Michigan’s clear clean water and twisted the cap shut. My plan is to carry this water to the Pacific Ocean—save it the trip down the Mississippi, across the Gulf of Mexico and through the Panama Canal.

Route 66 begins on the corner of Adams Street and Michigan Avenue. Actually, it begins and ends where Jackson runs into Lake Shore Drive, but that’s a one-way street ending abruptly in Lake Michigan.

After turning right onto Adams Street, I saw the sign: Historic Route 66 BEGIN.

Something about the stark imperative made me sit up straight and grip the wheel. I hit the gas with purpose and drove exactly half of the first block of Route 66. Then I had to stop because of the traffic.

Across the river and beyond, my first mile on the Mother Road was not a movie montage of fluid careless travel. Rather, Chicago brushed past me in stops and starts—bars without names, Polish Catholic churches with their mystic turrets, and brick box hospitals all separated by a slow parade of traffic lights. Over the course of an hour, I watched the city dissolve, shrinking lower and lower to the ground and then spreading out into vacant warehouses, empty lots, and bare stretches of brown earth.

Finally, the city was gone and I was turning right, then left, following the white-arrowed signs, determined to stay on the real Route 66.

It isn’t easy. Too much has happened since back then—too many things have changed and too much progress has happened. Sticking to the actual Route 66 is like insisting on using a Walkman in today’s world of MP3s and Spotify. You can do it (mostly) but you must be determined to ignore every invitation to join the faster, more efficient masses. At every turn, signs asked me if I really wanted to be traveling so slowly. Arrows and all-caps pointed to faster parallel highways that would get me there in half the time.

But I resisted.

I have always believed in the merits of slow travel—I can get pretty preachy about it, in fact, but even I got a little weary of moving through unplanted cornfields at 32 miles per hour. I passed through each small town like beads on a thread—Joliet, Wilmington, Braidwood—and smiled at the each cute dose of nostalgia placed within my driver’s seat view. Old-time gas pumps, polished Studebakers and ’57 Chevy’s, rooftop dinosaurs, glowing pink neon, and enough fake Route 66 signs to repave the Route 66—all of it seemed both charming and saccharine.

A lady beckoned from the road and lulled me to stop for dinner. It was Marilyn Monroe and she was fashioned from cement with red-painted lips. Inside the Polk-A-Dot Drive-In, the high school cross-country team laughed over mushy piles of chili cheese fries while younger kids toyed with the mini table jukeboxes. One little blonde girl threw some quarters into one and pushed the letters until the Everly Brothers began to sing “Dreeeeeam—Dream, Dream, Dream!”

Outside, cars pulled up and then drove away—the sky darkened and the pink neon switched on, spelling out, “Shakes, Hamburgers, Hot Dogs.”

I drove south, past more bare fields—a lone car on an empty frontage road, while just a few hundred yards to the right, a dozen cars per second rushed by in the opposite direction, all of them loving the ease of Highway 55.

Then I saw it, just to the right of me—the mossy bones of Route 66, laid out to rest in rows of neat square slabs outlined with weeds and grass. Even concrete breaks down over time, and these sections were all that was left of the actual road I’d been trying to follow.

I parked my car and in the fading light, wandered over to the ruins—a paved and broken line that pointed back to the city I’d left behind.

All that weedy crumbled stone reminded me of Roman ruins I have seen in the Mediterranean—this was even about the same width as those ancient roads. The difference is that in France and Italy, the cobbled roads date back some 2,000 years, while these bits of Route 66 were only around 50 years old.

Still, I felt as if I’d stumbled upon some great archeological moment in Central Illinois. Here was America’s Appian Way—the road that built an empire; a path of humanity racing westward that after awhile, fizzled away to rubble and dandelions.

Now, after my first full day on Route 66, I feel like I am driving into the past, sifting through decades of dirt and pulling up stone treasures of a forgotten country—my country. I may not be driving a red convertible or a handsome Camaro, but I am driving on the road that made all those cars mean something—and that means something to me.

Somewhere out there, across the grey grass and beyond the whispering highway, the sun offered up its final encore with a pulsing pink explosion that filled the entire sky. I drove towards the colored light but my eyes searched the darkness, following the skeletal outline in the grass—appearing and then vanishing, back and forth, the real Route 66—teasing me onward to the next small town on the map.


  1. Brian O'Kane
    Cork, Ireland
    April 18, 2014, 3:00 pm

    Andrew, good luck. Will be following in your footsteps in a few weeks. Joining my two sons on Route 66 for a 9-day roadtrip. We arrive Chicago May 15 – me from Cork, Ireland, Conall from Sydney, Australia and Kevin from Manchester, England. It’ll be my second Route 66 journey – last time in October 2008, on a Harley RoadGlide, with a group of other bikers fundraising for a children’s hospital in Dublin. We’re hoping for a convertible too – but out-of-state one-way rentals are discouraged so we may have to settle for a lesser beast – hopefully not a Malibu 🙂 despite the appropriateness of the name! Looking forward to following your trip – vicarious advance travelling! Good luck! Brian

  2. Laura Niemiec
    Michigan City, IN
    April 18, 2014, 8:26 pm

    Hope you have a blast! I traveled the route from March 31-April 5. Just posted a blog about the Illinois stretch ( Unfortunately I got caught in a downpour after Atlanta, Illinois so I plan to head back out one weekend soon and explore the stretch from Atlanta to St. Louis again.

  3. Mark Richardson
    April 18, 2014, 10:42 pm

    In May of last year I did the trip from OK City to Oatman AZ. …then in Sept of last did it from OK Cty to Chicago. Needless to say i’m jealous. Have a good time and make sure you stop by The Blue Swallow in Tucumcari and say hello to Kevin and Nancy!!

  4. Gill Grievson
    April 19, 2014, 2:12 am

    Hi Andrew. You caught my eye on a share on Facebook. Now I am hooked. Am all nostalgia just thinking about our 4 week trip on R66 in Sept 2012. We allowed 4 weeks. Could have taken four years. Would love to do it again, but it will never be the same as that first fab experience.

    • Andrew Evans
      April 19, 2014, 5:40 am

      Thanks Gill. Agreed, it is fabulous. I hope I can take a 4 full weeks, but already, I feel like I am going too quickly through beautiful Illinois. Glad you enjoyed it, and perhaps you need to come do it again!

  5. Ed Gowens
    San Diego, California
    April 19, 2014, 2:44 am

    “My plan is to carry this water to the Pacific Ocean—save it the trip down the Mississippi, across the Gulf of Mexico and through the Panama Canal.”

    The Mississippi River does NOT drain the Great Lakes! The St Lawrence River and Seaway drain them to the Atlantic, not the Gulf of Mexico.

    • Andrew Evans
      April 19, 2014, 5:40 am

      Good point, although through the Chicago River and canal network, then maybe, just maybe my bottle of water would have made it down the Mississippi! But yes, you are absolutely correct. Glad to see my readers are so geographically savvy.

  6. Vince Piccolo
    Largo Fl
    April 19, 2014, 4:47 pm

    For years-decades-my wife and I have talked about taking this trip. Now, with her retirement just a month away, we are looking forward to it, and we’ll follow your posts along the way. From Florida to Baltimore (granddaughter) then to South Bend Indiana for a week (easy train to and from Chicago), then from Adams Street to Santa Monica Pier. Expected travel time- 8-10 weeks. Cannot Wait to get started!!!

  7. David Morris
    Fort Mitchell, KY
    April 19, 2014, 8:07 pm

    Along with the Marilyn Monroe statue (sculpture?) at the Polka Dot Drive-in, and several others, there was one of Betty Boop. My 9 year old son was not familiar with her, but became so over the length of Rt 66 – Betty was a surprising Route 66 icon that we saw over and over during our drive.
    During our drive, we used my Prius for the first 3 legs (Chicago-St. Louis / St. Louis-Tulsa / Tulsa-Albuquerque). For the last two legs, I let my son choose the car we rented after flying to our starting point. In each case, he chose a black convertible Mustang. I have to admit that it was pretty cool driving into Vegas (a side trip), then across the desert, then into Los Angeles with the top down, even if it did give me the worst sunburn of my life after the first day, due to forgetting to put on sunscreen and also forgetting a hat. (My son is dark complected, so didn’t suffer as much.)

  8. Priscilla Bledsaw
    United States
    April 20, 2014, 10:36 am

    To all who travel “THE Route” , please stop and say hi to us at the Boots Court in Carthage Missouri (The Crossroads of America) We have worked so hard to produce a truly authentic 1940s experience here, and would love to show it to you even if you do not have time to stay. If you DO have time to stay, there really IS a radio in every room! lol.
    We are planning a 66 day Route trip in 2016. aybe we’ll see some of you on the way!

  9. Wei Li
    Beijing, China
    May 1, 2014, 8:13 am

    Hi, I am a woman from Beijing China. I just finish my Route 66 trip on 25th only one person. I leaved Chicago on 11th. Apr. it is a very short time, So, I will be come back again.

  10. M.R. Traska
    Chicago, IL
    May 21, 2014, 4:26 pm

    @Ed Gowens: Actually, Ed, you have it wrong: because of the engineering marvel that was/is the Sanitary & Ship Canal (completed in 1900), the flow of the Chicago River was REVERSED, so that Lake Michigan is drained by the Chicago River as well as by 3 of the other Great Lakes and the St. Lawrence River via the St. Lawrence Seaway. SO: Lake Michigan water goes not only to the Atlantic, but also via the S&S Canal/Des Plaines River into the Illinois River and then the Mississippi River, thus into the Gulf of Mexico. BTW, the NAE dubbed the S&S Canal oen of the great engineering wonders of the world. In 1999, the system was named a Civil Engineering Monument of the Millennium by the American Society of Civil Engineers (ASCE). And now, because of the damned Asian carp making their way up the Mississippi and Illinois Rivers, there’s wild talk of actually blocking the S&S Canal at about Romeoville, IL (where there’s an electrified net in place now) so that the invasive species can’t reach Lake Michigan.

  11. […] I traveled the entire length of Old Route 66, laying down some 2,500 miles of tire tread from Chicago to Los Angeles. Though I can now claim to know more of America than I had ever known before, my […]

  12. marie f
    April 4, 2015, 4:33 am

    doing trip in May,but dreading leaving Chicago with those crazy drivers,any tips

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