CA to NJ: Day 5 — A Long Road to Chicago

I know I said our next stop is Chicago, but Pop Pop and I had a way to go before we reached the Windy City. The road from South Dakota to Illinois was full of highs and lows. We started the morning with a visit to Sioux Falls, which is pictured below. However, our schedule for the day literally blew up when my tire blew out (I accidentally hit a curb a bit too hard — oops). Luckily, Pop Pop made a few calls as I calmed myself down by the water, and I was able to get a replacement tire. 

The mishap fortunately only put us an hour behind schedule, and we made it to my dear friend Kim’s place in Wisconsin right around dinner time at 6:30 p.m. I never expected to see a friend while driving cross country, but the route put us right through Madison, Wisconsin, where my friend relocated with her boyfriend after they graduated college. We had another Culver’s meal together, although it felt more like two separate dates too close in proximity. I say that because my Pop Pop is familiar with Kim’s boyfriend’s family, so they talked about that and work, while I caught up Kim on all the happenings in my life in the last few weeks. I was particularly fond of the dinner because Kim had two cute kittens, and the black one kept climbing up my Pop Pop’s leg for attention. It was an entertaining dinner, to say the least. 

Dinner was quick, because we still had a bit over two hours to go before arriving in Chicago. Once we did, our hotel did not have our reservation in the system, even though we confirmed our booking the previous night. Sometimes it really does feel like one thing after the next when traveling, but it’s all part of the deal. Having a perfectly smooth trip would be too boring! Luckily, I had screenshots of the reservation on my lap top, and they were able to give us a room. We were finally able to lug our suitcases at 10:30 p.m. from the parking garage a block away into our room. The room was super chic and I could totally see a social media influencer having a photo shoot there. 

The fun wasn’t over for the night once we arrived at our room, though. While checking our reservations for the next day, Pop Pop realized he accidentally booked a tour for the next month! Oops, again! Luckily, we were able to straighten that issue out and eventually hit the hay in anticipation of a busy day ahead.