Route 66 – (2018 Trip) – Day 2 – Chicago, IL. to Chicago, IL.


Chicago “The Windy City” according to Wikipedia, the term is used metaphorically to make out that Chicagoans were braggarts. The city is losing this reputation, for the reason that as people got used to it they found most of her claims to be backed up by facts. Our first morning in Chicago, today we decided to travel into town using Uber and we had breakfast at Lou Mitchell’s and have some breakfast. After breakfast we wandered up to the Route 66 start and finish signs on  W Jackson and W Adams streets. From there it was on to  Eagle Rider to collect our Harley-Davidson Electra Glide Ultra Classic. It certainly isn’t my preferred choice for touring, but you don’t get a lot of options with Eagle Rider. I guess I’ve been very spoiled on my Harley-Davidson CVO Road Glide all other bikes seem to be a step down from what it offers. Once we picked up the bike we braved the crazy traffic that only a large city in the U.S.A. can provide. I forgot how daunting it was riding through Chicago, mind you I’d only done it once before in 2013. Whilst we are travelling along Route 66 we planned to tick off some items for the HOG ABC’s of Touring. So today’s journey got us the Illinois, Indiana and Michigan borders, it’s a little bemusing to travel into 3 different states within a 174km (108 miles). Living in central Queensland the closest state border from me is 657km (408 miles) away. Since we were riding into Mighicigan we decided we might as well do lunch at The Stray Dog Bar & Grill. We found this place on Google Maps as we wanted to have a look at Lake Michigan from the Michigan shoreline. It is a popular joint that was pretty well full of customers. With full bellies and our sight seeing done we headed back to Illinois. The GPS on the bike must have slightly out of date maps, we got sidetracked a few times by following its directions. In the end I just rode back into the city so we could say we rode Route 66 from its starting point. From  for a quick stop in at Illinois Haley-Davidson. From there is was a short ride back to the motel which was out at Willowbrook it is around 34km to the Chicago CBD. One bonus we have that was unintentional, is that we are about 250 metres from the famous Route 66 Dell Rhea’s Chicken Basket. Dell Rhea’s opened in the summer of 1946 on Route 66. Because of the amount of traffic and distance from Chicago, the Chicken Basket was the perfect stopping place going to or coming from Chicago. We had to check out Dell Rhea’s Chicken Basket and hopefully get a photo of their famous neon sign. First up though we had to re-hydrate at The Kerry Piper. Next stop for us is Lincoln, Illinois.