My dad and I spent six days driving Route 66 from Chicago, IL to Santa Monica, CA. Our journey to Chicago began at 7:10am in Minneapolis on June 17th, Father’s Day. The original plan was for me to fly from Seattle to Chicago where my dad and his Corvette would collect me from the airport but I decided to fly to Minneapolis and drive to Chicago. Spending a couple of days in Minneapolis to visit friends and family and practice driving the car was not a bad thing and what’s another few hundred miles on top of Route 66’s 2,450 miles? Not much.
Beginning mileage day 1 = 10,630
The drive from Minneapolis to Chicago was roughly six hours. The midwest was in the middle of a heatwave and the humidity levels in Chicago were out of this world. It was the type of extreme humidity when it chokes you as soon as you walk outside.
We had three stops on our Chicago agenda:
- Skydeck at Willis Tower (aka Sears Tower)
- Route 66 start sign
- Cloud Gate
Our first stop was to the Skydeck. We purchased general admission tickets in advance. This was a mistake, not the “in advance” part but the general admission part. It took us one hour and 45 minutes to reach the ledge (“Skydeck”) after walking through the doors of Willis Tower. If I had to do it all over again, I’d purchase Fast Pass tickets.
The first half of the queuing process was civilized with roped lanes and people patiently waiting for their turn. The second half, however, was a shit show. There are four clear “ledges/boxes” that dangle over the side of the building and there were some loose queues for each ledge but it was more or less a scrum – just a massive group of people nudging their way to the ledges. It took us 45 minutes to get to the ledge after getting in the ledge “queue”.
The Skydeck was the type of attraction that makes me dislike major attractions. The ledges are tiny and people want photos of only themselves on the ledge. I saw people lay on the ledge, do handstands on the ledge, sit on the ledge, hug on the ledge, kiss on the ledge, do the splits on the ledge… There were some instances of people spending upwards of 5 minutes on the ledge which felt more like 55 minutes. It’s a selfish thing to do considering the thousands of people waiting and many people became agitated with this and the staff did nothing to help control the situation.
The Skydeck is also the type of attraction where cultural differences are very apparent. There are some cultures where taking up as much time on the ledge regardless of how many people are waiting is acceptable and there are other cultures that are keenly aware of the people waiting and hurry in and out.
I have mostly lost my American politeness when engaging in tourist activities. Gone are the days of waiting patiently for people to take 438 Instagram photos and the reason for this is because it’s rare that the pleasantry is returned.
After our visit to the Skydeck, we walked to the Route 66 start sign located near Millennium Park. I was dripping in sweat when we arrived at the sign. I can no longer handle heat after living in England and Seattle for the past seven years. My dad, however, does not sweat.
My armpits were soaked and there was sweat literally dripping off of my face and I’d look at my dad and he’d be bone dry as though it was 55 degrees and negative humidity. It was the first of many times during our sweltering trip when I wondered if we were related but then I’d look at the photo above and I’d be reassured that I am, indeed, my father’s daughter.
Our third and final stop in Chicago was to Cloud Gate (aka “The Bean”) in Millennium Park, located just around the corner from the Route 66 sign but instead of going straight to Cloud Gate, we decided to go get the car and drive to the Route 66 so that we could take a photo of the car and the sign, you know, to prove the car actually started at the start of Route 66. The lesson I learned from photographing the car at the Route 66 start sign was that we needed to ensure the car was turned off when being photographed because of the attention-grabbing brake lights.
After the car/sign photo, my dad drove me to the entrance of Millennium Park where I hopped out and ran to the sculpture. There was a festival going on in the park and thousands of people everywhere. Thousands of crazy people because no sane person would spend more time outside in that heat and humidity than absolutely necessary.
I snapped a total of photos of The Bean (there were too many people to get a decent shot) and then I ran back to the park entrance and waited for my chariot to arrive but it was stuck in traffic and the tangle of one-way streets. If we had to do it all over again, we would have walked from the Route 66 start sign to the park, taken photos of Cloud Gate, walked back to the car, and then driven the car to the Route 66 start sign and taken photos.
By the time my chariot arrived at Millennium Park, I was a literal hot mess. My shirt was more wet than dry. My socks were soaked as though I just ran a marathon and my hair had that “just out of the shower” look. The humidity reminded me of the humidity in Bangkok and I wanted to shed a tear in discomfort but there was no liquid left in my body.
From Chicago, we drove to Bolingbrook and stayed there for the night. We checked into the hotel and went to a bar for beers, a bite to eat, and to plan the stops for the following day.
| Beginning mileage day 1 | 10,630 |
| Ending mileage day 1 | 11,103 |
| Total miles driven day 1 | 473 |
In the months leading up to the trip, my dad and I researched stops and attractions on Route 66 and added them to a spreadsheet which you can find here.
I added voting columns to the spreadsheet where we each voted yes, no, or maybe for each stop/attraction, and then I created a custom Google map with the color-coded yeses and maybes. The Google map provided us with the level of detail needed to figure out where we would stay each night and it served as our compass for the entirety of the trip.
The following morning (day 2) we departed Bolingbrook at 7:10am. For us, Illinois was the state with the most stops/attractions. It felt like we were driving in Illinois for days. We drove Route 66 (versus the major highway that runs parallel to it) for most of the Illinois segment but once out of Illinois, the tires only touched good ol’ Route 66 once in each state. Most people who set off to drive Route 66 reserve a couple of weeks to complete the journey and we did it in a fraction of that time.
I estimate that it would take 6-8 weeks to drive the original Route 66 from start to end, stopping at all of the Route 66 attractions along the way. The only feasible way to do this is to have a very flexible schedule with no time limit and either drive an RV or tow a camper. There is simply too much dead space in some stretches of Route 66 where accommodation is not plentiful and/or is undesirable.
Our first stop on day 2 was at an original Texaco service station named Ambler’s Texaco Station. There are many old service stations along Route 66 but this was the best one.
The service station was well-maintained and it had old cars in the garage and original gas pumps. There was also a nice mural on the pavement, one of my favorite Route 66 murals we saw during our journey.
We left the service station and I had high hopes that all of the stops would be this neat but that is not how it played out. We hit a couple of duds along the way which was disappointing and ate up a lot of time. If you are planning to drive Route 66, then estimate that each minor stop like the old service station above will take 15 minutes and then double that estimate because not only will the stop take 15 minutes but you’ve delayed the mileage you’d be driving if you were traveling during that 15 minutes you were stopped.
From the service station, we drove Route 66 and eventually stumbled upon an original strip of Route 66 asphalt. We pulled the car over and parked it on the original asphalt and were greeted by a local farmer whose land we were parked on. He was a friendly fellow and enlightened us on the politics of farming and all of the people he has met over the decades driving Route 66. Russians, Australians, Chinese. He went on and on. It is people like this farmer who make me have hope for my country. He was just an honest guy trying to make an honest living and live his best life.
The farmer recommended that we stop in nearby Pontiac and check out a few of the city’s 23 murals, collectively named Murals on Main Street. He explained that Lipton Tea had just been in town painting a new mural. I imagine this was front-page news for many weeks in the local newspaper.
In need of a bathroom break and interested in the murals, we stopped in Pontiac. Pontiac is very “Small Town USA”. There’s a bakery, a coffee shop, a fire station, and a few restaurants and bars. It is not somewhere I could live but I can see the appeal of living there. Life just moves a bit slower in Pontiac, possibly a little too slow.
The main mural attraction is the gigantic Route 66 Shield Mural located on the back of the Route 66 Museum. The mural is so pristine that it looks fake.
The Davenator and I meandered around the city taking photos of various murals and then we stopped at a local coffee shop for some caffeine and then hit the road again.
Our next stop was the Railsplitter Covered Wagon. It was one of those stops that was not too far off of Route 66 and “would only take a couple of minutes”. It was after this stop when we realized that no matter how minor the stop, it would cost us 30 minutes of time between stoppage and lost driving time.
The Railsplitter Covered Wagon was a total dud – avoid stopping here, unless of course your fancy seeing the world’s largest covered wagon, which you do not. Just trust me on that one.
I felt defeated after our stop at the Railsplitter but was looking forward to driving on a 1.4 mile stretch of restored original Route 66 brick road. This stretch of road is located just north of Auburn and directions to it are well-marked off of what is now known as Highway 4. It was bumpy and narrow and I imagined driving this road in a 1930s Ford and thought how awful of a journey that would have been and how long it would have taken to drive from Chicago to Santa Monica at the blazing speed of 40 miles per hour.
We crossed into our fourth state of the trip, Missouri, around 11:30am on day 2 and felt a sense of accomplishment even though we still had a very long way to drive that day. We were so happy to be out of Illinois!
Stay tuned for all things Missouri.
Yawning gets you everywhere 
Great photos!