Here is day 1 of my Route 66 trip. For tips on planning your own trip see my story about planning here (https://flipsdipsandtrips.com/helpful-tips-to-plan-your-epic-route-66-road-trip/). Route 66 starts in Chicago and ends in Santa Monica California. I live in Ohio so I naturally started my trip in Chicago. I had no plan for the day except the Museum of Science and Industry and the Sears Tower. It ended up being a day of towers, prison, and chicken.
Car Troubles
The night before I had a dance recital and had to wake up at 4am to get to Chicago by 10am. The drive to Chicago started off normal until I got to Indiana. That’s when the issues with my 2015 Chevy Cruze started.
I must’ve sped up too quickly coming out of a toll booth and threw off my transmission or something. My car went limp so I got off at a rest stop. My car refused to turn on but after a few minutes it started. I was shaken but as long as my car worked I was fine. If i had anymore issues I was going to leave my car in Chicago and take a rental the rest of the way.
Downtown Chicago
I arrived in Chicago around 11 and went straight to the Museum of Science and Industry. It is a beautiful building from the 1893 Columbian Exposition. They had all sorts of exhibits about science like how the human body works and how electricity works. They had trains, planes and even a submarine you can walk through. I wish I spent more time there but I was so concerned about my car that I left earlier than I wanted just in case I had to take it in.
Officially on Route 66!
After the museum I drove to the intersection of Michigan and Adams where Route 66 starts. I found an illegal parking spot, threw on my hazards and ran over to the Route 66 Begin sign. Then I took my pictures and listened to a homeless guy brag about how he invented the Ninja Turtles and ran back to my car. I then proceeded down Adams to the Sears Tower (I know, I know, I’m still going to deadname it).
The Sears Tower is the tallest building in Chicago and in the world for more than 20 years. For about $40 you can go up to the top. At the top you get a bird’s eye view of Chicago and Lake Michigan. Included in admission is The Ledge which is a glass box off the side of the building. After the Ledge I took the elevator back down. Lastly I paid the $50 for my hour long parking stay and headed west on 66.
On 66 I passed through Chicago and took a blurry photo of the Castle Car Wash where Al Capone hid out at one point. I then pulled up to Henry’s for my first meal of the trip. Its a small place famous for its hot dogs as it has a giant Chicago Dog on its sign. I had a chili dog and fries and then got back on the road.
On to Joliet
It was only 2pm since I cut my time short at the museum and I wasn’t ready for my dinner yet so I decided to call an audible. I didn’t plan on visiting until the next day but I really wanted to maximize my time and see everything so I decided to visit the Old Joliet Prison.
Parts of the Blues Brothers was filmed there but I am not a movie person so I had no idea what that was. It cost about $20 for a self guided tour. Bring tennis shoes because it is a lot of walking on uneven surfaces in the yard and the cell blocks. Everyone was super friendly and helpful and I was pretty much the only person there.
After the prison I stayed in Joilet to get ice cream at Rich and Creamy. It is an iconic ice cream place on Route 66. The Blues Brothers are on the top if the stand and it is next to a park. I walked around the park and took some pictures before heading to my hotel. It was cicada season so you could hear them screaming even in the car and they were everywhere around the hotel.
I got checked into my hotel in Darien Illinois and got ready for the meal I was looking forward to all day. The Chicken Basket is an iconic restaurant on 66 serving fried chicken. It is one of my favorite restaurants in the country and I always try to stop there when I’m near Chicago. I had chicken obviously with green beans and their salad bar. After dinner I took some photos and headed back to my hotel. The next day will take me to Springfield which is the capital of Illinois.
