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Of all the cities we’ve visited in the USA, Chicago had was definitely the worst for driving in. I don’t think I’ve ever been more stressed out at a GPS system. We had a midday deadline to get our rental car dropped off at it’s Chicago location, and foolishly hadn’t quite realised how long it would take to drive from our previous destination onto our final city. It was 5 hours from St Louis to Chicago, our last stretch of Route 66 (but with not too much to see on the way) so we started bright and early and hit the road. We made it to Chicago in good time, but once we hit the interstate directly into the city it was all downhill. Over an hour of driving in circles trying to find the right one-way street that would get us to where we needed to be, yikes. We were more than happy to drop off the muscle car by that point! 

Chicago itself is beautiful. We weren’t really sure what to expect, but were pleasantly surprised. The only item on our list of must do’s was eat deep dish pizza (Joshua) and visit the Art Institute of Chicago (Megan). We managed to knock off both our items on the first afternoon we were there, so we were off to a good start!

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Our hotel was located just a stroll from Michigan Avenue, so we wandered up to the Art Institute of Chicago a little over an hour before closing. We nabbed half-price tickets for the final hour, so we spent the next 60 minutes hurrying through the levels to tick off all the must-sees. I allotted a few more of my minutes to the room housing all the Monet’s, and it was a good thing too as I got all weepy and needed a couple of minutes to recover. There’s something about his work that is just so magical in real life, and totally unexplainable, but completely beautiful, all in one. We also were able to see Seurat’s ‘A Sunday Afternoon on the Island of La Grande Jatte’ - and while it didn’t make me cry, it did leave me quite gobsmacked at just how clever it is and how good pointillism can be. Definitely one of my favourites I’ve seen in the flesh! 

Anish Kapoor’s ‘Cloud Gate’ is next door to the Art Institute, so we popped over for some people watching and selfie taking in the reflection. The Bean is beautiful (when you’re not thinking about how dirty it must be from all the birds sitting on the top of it, and how many people touch it all day long) and seeing the level of interaction it gets is really interesting. It wins the award for the best public sculpture I’ve ever seen.

Deep Dish Pizza was Josh’s culinary Holy Grail of our trip. We were nice and close to a well celebrated pizza place, famous for their butter crust on the deep dish sausage pizza pie. It was pretty full on (the furthest thing from healthy eating we could have possibly gone for), cheesy and tomato and all sorts of carbohydrates, although the happiness on Josh’s face was worth every calorie!

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The weather was unseasonably cold while we were in Chicago, dipping to 5 degrees Celsius on our second morning there, as well as raining. We had anticipated warm weather, and left coats and jackets at home in Australia - so we spent the better part of the day shopping for a jacket (and making the most of indoor heating). We walked along the Miracle Mile, admired the beautiful buildings and watched boats sail along the river. We did an awful lot of pavement pounding in Chicago, one of the few cities we didn’t use a car or public transport in. A second visit to The Bean (it really was worth a second look) and hunting down the sign that marks the very end of Route 66, we loved our brief time in Chicago!

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