Route 66 planning


Driving Route 66 can be a once in a lifetime opportunity. This was a trip a wanted to embark on with my best friend of the past 30 years. My best friend Leah and I had talked about driving Route 66 for at least a few years before deciding it was time to stop talking about it and start planning it. I started by searching flights from Los Angeles to our hometown of Cincinnati. I found a great deal and purchased the tickets. I looked at different maps and bought a few books to learn about the things we could see along the way. I talked to my mom about the trip, and she recommend that I read a book that she read called Driving America’s Main Street Route 66 Still Kicks by Rick Antonson. I read this and took notes about the places he and his friend stopped at on their journey.

After I read that, I watched, Cruising Route 66 with Michael Wallace. I wouldn’t have known about the show if it wasn’t for the book my mom recommended. Although a little outdated, Cruising Route 66 was worth watching. I got out a notebook and started making notes about the stops Micheal Wallace he mentioned. I also downloaded an app called Route 66 Travel Guide. Using these tools I created an itinerary, booked our hotels, and finally, I rented a car.

Leah and I agreed that we should drive to Chicago the night before so we could start our journey the next morning refreshed and ready to go. I left work early that day. I picked Leah up and we headed to the airport to get our rental car. I started out driving to Chicago. This is about a 5-hour drive, depending on where you are staying.

It was also Leah’s birthday and she suggested we go to Portillo’s for dinner. In all the times that I have been to Chicago, I don’t think I had ever eaten here. This is a Chicago restaurant serving hot dogs, Chicago beef sandwiches, hamburgers, French fries, and more. The one we went to was full of old school Americana. It suited our Route 66 trip well. I ordered a Chicago Beef Sandwich. The sandwich was way bigger than I thought.  To celebrate Leah’s birthday, I also ordered a piece of chocolate cake for us to split.


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