We arrived in Chicago around 6pm. It may have been 7pm, but we couldn’t figure out what time it was because of the time zone change. The first place we tried to go was Lou Malnati’s pizza but our GPS had other plans. Two years ago we were in Chicago and had the same problem, but we’re both stubborn and kept trying to follow the gps. Due to the tall buildings, the gps has a delay. It tells you to turn a few minutes AFTER you’re supposed to turn. Then it reroutes you and starts all over again. Luckily traffic wasn’t that bad as we drove aimlessly around the city. Eventually we made it to Lou’s. After the standard one hour wait, we were seated and devoured our pizza!

We left the pizza place around 8pm or 9pm (depending on who’s phone you looked at) and began our search for the beginning of Route 66 sign. We found it. For such a historical, iconic route, we were surprised at how small the sign was. As soon as we passed the sign, I admitted to Eddie that after all the research I had been doing, I had no clue where to go next.

For those of you who don’t know, Route 66 was decommissioned in 1984. A few years prior, parts of the route began being replaced by interstate highways. This can make it especially challenging to figure out where the heck the actual road is or was! After several wrong turns and wrong ways on the highway, we actually figured it out! It turned into a 3 hour scenic drive scavenger hunt through half the state of Illinois. It’s sad to see how run down and dilapidated some of the historic buildings are. If it weren’t for the help of a Route 66 app I found, we probably would have passed by half of the places we saw thinking they were abandoned buildings.

Throughout this adventure we learned a few things:

1. If a person can actually find the Route 66 signs and stay on the road without getting lost, they deserve a medal. It is hard and discouraging.

2. If one wanted to see all of the listed tourist stops on the entire route, (IL – CA) it would probably take 2 months. It is all backroads with random turns. At one point we encountered a sign that told us the next turn for Route 66 was either right OR left. Rock, paper, scissors helped us out there.

3. Teamwork is key. Alone, Eddie and I would have given up on this journey as soon as we realized what it entailed. But, together, we figured it out and had a blast in the process.

We’re now checked into our hotel for the night. The first place on the list for tomorrow is The Route 66 museum in Pontiac, IL so we can come up with a new strategy to figure out how we’re going to follow this route.

On a side note- there’s tons of flying insects in IL. I got pretty bitten up today. I also read the news report about the massive grasshopper invasion that we’ll be enjoying in Las Vegas next week. I’m slowly gaining a new appreciation for the CT bugs who don’t swarm you as much.

More tomorrow.