Welcome to my Route 66 Daily Roundups. Throughout the course of my cross-country adventure with and vehicle sponsor , I will be sharing the highlights from each leg of the trip. To see all of the Daily Roundups please click here.
To read about the inspiration for this epic drive, please check out this post.
Pre-Trip Preparations – Chicago
I’ve been planning this trip for a very long time, scouring over scores of books and maps in order to organize the best possible trip. Part of that was making sure I spent some time exploring the starting point of the adventure, Chicago. I didn’t just want some time to buy provisions and get used to the vehicle, but I wanted to play tourist in Chicago – a city I’ve seen very little of in the past. I wanted to correct that on this trip and I was excited to finally see some of the city’s most iconic landmarks.
November 11, 1926 – that’s the date when this all started, when Route 66 was officially created. What must have at the time seemed little more than a simple act of transportation management created generations of adventurers, eager drivers tackling the Mother Road for thousands of different reasons. Whether it was seeking a better life during the Great Depression or enjoying the highlife of post-war America, everyone has their own reasons for driving Route 66, their own stories and I’m excited to add my own narrative to that ongoing conversation.
Chicago is called the Second City, not because of any comparisons, but because of how many times it has risen from the ashes. After the Great Chicago Fire, when more than 18,000 buildings were destroyed, Chicago built a brand new city. Then after the collapse of its booming industries in the 1930s, it once again rebuilt itself. The 21st century is a good time to be in Chicago, as I learned while enjoying a perfect summer day and a lot of touristy explorations.
Since it was my first time playing tourist in the city, I had a list of key sights I wanted to visit. Arriving into Chicago, I first checked into the newly opened , a beautiful hotel that has some of the best design and style elements I’ve ever seen. It’s also a great home base to see the best of the Windy City. Since I didn’t have a lot of time, I bought a Chicago CityPASS to make the most of my day. What I think is the real value of the pass isn’t the savings, it’s the complimentary access to the Fast Track lines. That alone saved me hours of waiting at the Willis Tower, time I really couldn’t afford to lose.
To see the best of Chicago, I ascended not one but two different towers, the Willis Tower and the observation deck at the John Hancock Center. While very different experiences, both gave me those views I was looking for, and both set the stage for a fun day in the city. The highlight of my day wasn’t just one building though, it was all of them. Taking advantage of the , I booked a tour I’ve wanted to take for years, the famous Architectural River Cruise. The Moments marketplace is a new feature offered by Marriott Rewards and one I’ll be taking advantage of throughout my trip. The marketplace allows members to both earn and redeem points by shopping for fun travel experiences, like the river cruise. The cruise is a 90-minute trip through the center of Chicago, while an expert docent shares the history of the city through its iconic architecture. I knew I’d enjoy it, I just didn’t know how much. It helped that the weather was perfect and everyone was in a good mood as we floated through the middle of the city on what truly is one of the best tours in the world.
I also spent some time over the weekend getting ready for the next two weeks of driving. As I mentioned in my preview post, the vehicle sponsor of the trip is Nissan, and our first truck of the trip is the mighty Armanda Platinum. As soon as I sat inside the SUV I was in love, from the comfy seats to some very impressive technological features, it’s the perfect truck to help me experience the best of Route 66.
Monday is the big day though, it’s when we finally hit the road and start our adventure along the Mother Road. Please remember to follow along on and let me know if you have any questions!