Chicago, Illinois

One word to describe the city: Spacious

Cost per person: 160

Kilometers driven: 1,750

Hours spent: 16

Attractions/Sights: See here

Rating: 11 out of 12

Ideal Visitor: Any city enthusiast


360 days after we left New York, we were on the I65 navigating our way into the final city of 12 in 12. Chicago! Appropriate as our last city in many ways, what stuck out to us on the drive in was how similar the feeling was to pulling into New York. It was the only city to compete with NY in terms of size, it had that big skyline view as you got closer, and it was accompanied with the same sense of “Icantbelievewedidthisissocraywowwa” ovewhelming all of us. Chicago here we come!


Skyline + dirty window

We got into the city in the late morning and promptly found parking. This might have actually been one of our easiest times finding our way to parking over all 12 cities and it was a welcome and pleasant feeling. After bundling up to protect against that wind we were off. One reality for us in this city was that we weren’t going to be able to do everything. Now wait a minute, you might be thinking- you didn’t do everything in any other city either! And to this I say true, however it felt more evident here as there were so many big things to do that it felt like just a snapshot in more ways than some of our smaller cities. In order to get a lay of the land we headed to the worst place in the world:

libraryJust kidding. While I agree with Leslie Knope on many of life’s issues, this was not one of them. The Chicago Public Library was clean, pleasant, and had free wifi. What more could you ask for? It also had a very different vibe in comparison with some of the other libraries we have visited. Very light and marble filled. See exhibit A, a photo of a light filled atrium on the 9th floor:


From the library it was a 5 second walk to the nearest L train station. We were hoping to witness a magical moment along the following lines:


Alas, we witnessed zero proposals to a transit employee from the brother of the guy she pretended to be engaged to while he was in a coma. We didn’t think that was a lot to ask so this was probably the most disappointing part of our day.

A short ride later we arrived at the Field Museum. After our traditional ham and cheese sandwich plus carrot lunch we were ready to take in all the long dead animals. A small selection of photos so you can experience it right along with us:


Great question. Class?



Whimsical zebras


I can only imagine how difficult this would have been with only moderately cordial folks on the case.




Time to get down


Suffice it to say there was a lot to see at the Field Museum and we enjoyed it thoroughly. Some of the animals were taxidermied in the 19th century! So yeah, it was pretty legit.

Our next step was to walk through Grant/Millennium Park along with the necessary Bean selfies. Won’t bore you with too many but it is important to note that it is worth the buzz. And as we discussed extensively on our trip whoever originally thought of it was a super genius. That thing has paid for itself in free publicity.







By this time we were ravenous. Of course we couldn’t leave Chicago without eating deep dish pizza, and our pit stop did not disappoint. Man we did so much that day, I can’t believe this post isn’t over yet. Doesn’t it feel long to you?

After dinner we had planned a late night Chicago adventure, given that we were staying the night (luxurious I know) and we could! We wandered down by the river and the Magnificent Mile just taking the city views in.



After that we hopped on the train and made our way over to the Improv Olympic for an improvised musical. We were skeptical going into it but it was very well done and very funny. Recommend to all!

It felt bizarre to still have so much time ahead of us given that we are used to hightailing it out of the city once the day is over. This was a special one though and we planned to finish with a pop. A pop of champagne:


This was literally a bar just to buy champagne at. We bought one of the cheapest bottles and enjoyed ourselves thoroughly. What a luxury at the end of our year long adventure!


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