Driving historical route 66: St Louis to Chicago

The last leg of our journey on Route 66 from Los Angeles to Chicago, was supposed to be driven on August 21st after the total solar eclipse, but things didn’t go quite as we had planned. Getting out of the park, where we watched the eclipse, was easy enough, but getting from Carbondale to St Louis, where the last leg of Route 66 would begin, proved much more time-consuming than we had ever imagined. It seemed like the entire city of Chicago had come to Carbondale to watch the eclipse. The queue was enormous. We were driving along at snail’s pace.

Everyone was going the same direction as us, at least until we were able to turn off for St Louis instead of Chicago, where the queue continued. At 9 PM, we finally arrived in St Louis, exhausted after 7 hours on the road. Usually, it would only have taken 2 hours to drive from Carbondale to St Louis, so we could’ve easily made it to Chicago from there as well, but that would have to wait for the next day, leaving us with only half a day to explore the windy city. Thank goodness for the car deal we got, when we had to miss out on the Death Valley!

We stayed overnight in Motel 6, and then left early the next morning for Chicago via the historical Route 66. For the first time on this trip, it was actually raining when we got up! I was really happy for the change in temperature, as we’d been sweating in 40+ degrees the day before!

Route 66 is represented by 289 glorious miles through Illinois, heading diagonally across the state, passing through endless fields of corn for as far as the eye can reach in this Prairie State. But this flat and lush agricultural state of the Midwest also offers several atmospheric Route 66 towns that each have their own charm and distinctiveness.

Route 66 continued for a bit longer after the Ariston Café (pictured above), before becoming highway once again. We followed the highway to Springfield, the state capital of Illinois, and then turned off towards Lake Springfield, just to get some nature that day as well.

After Springfield, there’s quite a bit of Route 66 to be followed, going through several quaint villages, before getting to Odell, where the next sight on our list is located.

One of the beautiful examples of classic gasoline stations along Route 66 is found in this small town, where the locals have restored an old Standard Oil station. Originally built in 1932 to serve traffic along the historic highway, the building has now become a popular stop for Route 66 travellers on their way eastbound to Chicago or westbound to LA.

Unfortunately, we had to hurry through the last stretch of Route 66 quite a bit so we could spend our last afternoon exploring Chicago, so we didn’t get to stop as often as we would’ve liked.

We arrived in the easternmost point of Route 66, the center of Chicago, at 3 PM, and paid a whopping 28 USD to park in the city center!

The heat in Chicago was so much more bearable than anywhere else in the country. It was more of a dry heat with wind instead of the stuffy heat that we had gotten used to. I LOVED the change in weather and the fact that we could actually walk about without getting heat strokes.

We first walked to the Buckingham Fountain, a famous Chicago landmark located in the center of Grant Park. I LOVE fountains and this one was definitely one of the most beautiful fountains I’ve seen with its rococo wedding cake style architecture. It’s also one of the world’s largest fountains!

We then walked down to the harbour and hung out there for a while, while feeding ducks and people-watching. It was like a small cozy harbour town in the middle of a ginormous city – and I loved that atmosphere!

Into the city center we went, across the BP Pedestrian Bridge, which is a bridge unlike anything I’ve ever seen before. It’s a girder footbridge, which has won many awards for its use of sheet metal and for its unique design. It spans Columbus Drive to connect the Maggie Daley Park with Millennium Park, where we were headed next.

The Millennium Park is home to the fun Cloud Gate sculpture, also known as “The Bean”. The sculpture was designed by Sir Anish Kapoor and constructed between 2004 and 2006, made up of 168 stainless steel plates welded together, and then highly polished so no seams are visible. We, among hundreds of other tourists, took selfies with The Bean with ourselves, the sky and skyline reflecting in it.

We then walked across Chicago River across the Michigan Avenue Bridge to the skyscraper district on North Michigan Avenue, where we saw many famous bildings, including the Trump International Hotel and Tower, named after the infamous President Donald Trump, and the John Hancock Center, from where there’s an EXPENSIVE observation deck. We decided to save our money this time around, as there are so many other great spots for skyline viewing in Chicago.

We ate a last dinner in the US at Fridays, which was a delicious avocado and bean burger with seasoned fries and coke with free refill (why don’t all restaurants have that!?). It was our version of a perfect goodbye-dinner in the States!

Fair enough…

We then walked to Oak Street Beach, a nice little city beach on North Lake Shore Drive, where locals were hanging out and playing volleyball.

We had one last thing that we really wanted to see in Chicago – the official Route 66 starting point!

We walked back down North Michigan Avenue and found the signs for the starting point (but our ending point) on East Adams Street. From Santa Monica Pier in Los Angeles to East Adams Street in Chicago, we had now travelled 2274 miles across the United States of America, and that’s without the many detours! What a great journey it had been!

When we were done sightseeing in Chicago (although there is so much more to see!), we headed for Motel 6 near the airport. I drove through the very center of Chicago, which was quite scary at first. I think I’m getting used to driving in enormous cities though, as I’ve now done it in LA, Las Vegas and Chicago. I still would never dare to do it in Copenhagen or Amsterdam, where there are cyclists EVERYWHERE!

I really enjoyed our time spent in Chicago. It’s a beautiful city with so much to offer, and I could’ve spent much longer than just one afternoon there. I wish we would’ve spent more time in Chicago rather than LA!
Chicago was very much my kind of city. Close to the water with plenty of activities to do, beautiful skyscrapers, a river flowing through its very center, and full of friendly people. I could easily imagine living in Chicago. In fact, I’m even considering taking a semester there, if I can find a course that interests me! But no matter what, I’ll be back someday!
Chicago was the perfect end to our Route 66 journey and American adventure. We both enjoyed it so much more than LA, and were thankful that we had taken the Route 66 the “wrong way”, so we saved the best for last! We can recommend going against the norm and starting in LA heading eastbound, rather than Chicago heading westbound! 😉

On August 23rd, it was time to head back to Denmark after two wonderful weeks in the US. We drove our rental car to the Hertz drop-off area in the O’Hare airport and I felt a sting of sadness as we left it behind. We had experienced so much in that car. It had taken us all the way from Las Vegas (after we exchanged it there) to Chicago, and it had witnessed a total solar eclipse with us. Also, it had automatic gear!!!!! That’s the thing I miss the most, for sure! 😉 In fact, the first time I drove a car back in Denmark since the trip, I stalled 7 times in just 10 minutes…

We left Chicago at 2.35 PM and were off on a long journey, first to Frankfurt and then to Denmark, where we arrived safely on August 24th at 9 AM, with the biggest layover ever! I’m telling you, it was good to sleep that following night!