Chicago

Having come from Boston, my fav US city to date, I was a little concerned that every other destination remaining in this leg of my journey would pale in comparison. But, Chicago has always been a city that interested me so I had my fingers crossed I wouldn’t regret the nine days I booked here. As it happened, nine days went by in a blink – Chicago is cool AF with so much to do (especially when you spend a chunk of your time running every day). I had a fantastic time here. Distinct from Boston and hard to compare directly, but Chicago is now running a very close second place!

Early in my time here, my debit cards had arrived in Australia which gave me the ability to add them to my digital wallet *happy dance* I can now tap and pay and use my cards to book things in online! So, I booked lots of super fun things! The re-call of Uber to my travel inventory was probably the best part – public transport can’t get you everywhere and I was getting sick of walking long distances with my baggage.

I stayed in the Lincoln Park area (you have no idea how much self-control I exercised to not post to my IG story with Linkin Park music everyday) which was one of my better decisions. Lincoln Park has a heap of great places to eat and drink (including a fab acai bowl joint) and I was in short walking distance to the running trails along Lake Michigan yiew. The trains also go straight to the Loop every few minutes so I could easily get to downtown.  

It didn’t take me long to get myself to a comedy show, I got my stand-up fix at Laugh Factory but my highlight was a sketch/improv show at the Second City. I have never laughed so hard for so long. I had tears running down my face uncontrollably. The cast were phenomenal. God I love comedy. How good is laughing?

The day I arrived in Chicago was Memorial Day so most thing were closed, but in my local walk around (I do this as soon as I get in somewhere new to get my bearings) I noticed a little coffee place that looked like an actual coffee place so I made a mental note to give that a try the following day. Turns out my instincts were on point and café Ludlow Charlington’s was my latte option eight days straight! No flat whites on the menu but beggars can’t be choosers.

It took me a few days to find a deep-dish pizza restaurant (entirely from a lack of trying) but I eventually tried Lou Manati’s to see what the deep dish is all about. In short, delicious. If you are unfamiliar, the pizza is on a corn-based crust (basically polenta) that gets super crispy. The toppings are around an inch thick and just super cheesy-tomatoey goodness mm mmmmm. I had locals suggest trying Pequod’s for another authentic experience. Neither disappointed, the deep dish is goooooood. Sandy approved. I’ll probably never have pizza in Australia ever again.

I learned myself a thing or two about architecture in Chicago from the exceptional vantage point of the river (on a boat, not doggy paddling). I thought these tours might be a bit of a tourist trap but every single local I asked recommended the architectural cruise and told me that Chicagoans also do them for fun every so often. A very relaxing way to see the city!

I did a brewery hopping tour in a barrel styled vehicle, aptly named the Barrel Run. I had too many beers that day and a lot of fun. I suspect this business model would be wildly successful in Australia, which I told the CEO (who was our guide).

The history museum here was excellent. I now know all about the fire. And Abe Lincoln.

I ummed and ahhed about whether to head up to the top of Sear’s Tower (its official name is Willis Tower but Chicagoans get very snarky when you call it that) mostly because it was a bit pricey. But I decided a trip to Chicago is not complete without seeing the Skydeck. 103 floors above the ground, the views are extraordinary. I’m glad I spent the money. I did also do The Ledge add on where you walk out into a glass box 440m up! I’m not particularly bothered by heights so I absolutely loved it. It was wild though. The most annoying part of this experience is that you only get 60 seconds to take in your ledge views. Although I understand that some would argue that’s 60 seconds too long, it’s not long to take in where you are and then hastily take a few photo’s so you can freak out your family and friends. One of the coolest (and slightly unhinged) things I’ve done so far!

I also entered myself in a local fun run, I had expected that this wasn’t going to be the most serious of races given that the name of it was ‘Run for Beer’ haha (it started/finished at a local brewery, yes I have now been to a few). A portion of your entry fee supports local non-for-profits and the motto of the organisation is ‘Be Active, Have Fun, Give Back’ so I figured it was a good idea. I had so much fun that day. A very relaxed vibe and a very relaxed course (we had to cross a heap of roads that were not closed including a five-way intersection – chaos!) but everyone there was running without complaint, and I even happened to get myself a little victory – unsurprisingly rewarded with more beer for my effort! Everyone was so friendly, and I got to chat with a few like-minded locals which was great. This was one of those real cup filling mornings.

So. Running in Chicago, at least as a tourist, is brilliant. The running/cycling paths along the lake are just suh gewd. I think the south bound run from Lincoln Park is in my personal opinion (which is what you signed up for) the best urban run you could do! There are views of the city skyline, Navy Pier, various beaches, the marina, and you can run all the way down past The Observatory. The north bound run was also great, whilst slightly less visually spectacular it’s a little less busy so extra points for getting in faster sessions without the crowd. Around/through Lincoln Park are a few ponds which also have running paths around them that are lovely. Whilst it was a little out of the way I took myself out to the ‘burbs and ran the 606 which is meant to be the Chicagoan version of the High Line as it’s a path of old train tracks. The NYC high line is prettier as it runs through the skyscrapers but the 606 is much more running friendly, you couldn’t run it in NYC as it’s too crowded. Despite the fact it runs a dead straight line it’s not a boring run, it’s a little undulating and the paths run through residential buildings. The path is tree lined too giving a bit of shade - summer is here ooft. Garmin says I am 100% heat acclimatised now, first time for everything – lol. Throwing in my little fun run and I’ve had a great bunch of runs here and starting to feel nice and fit - hoorah!

Just something I feel like I want to share – the lake here looks a whole lot more like the ocean than the ocean did in Boston. But I swam (briefly waded) in it and it’s definitely a lake. A very cold lake. And some people were swimming in it (like, swimming for fitness not for recreation) and I just do not know why.

Once again Taylor Swift followed me to another city – once again I got to glare at every Swifty I saw running around in Eras merch or dressed up for the show. I came very close to forking out a lot of money to go because I just really want to. But I will wait until she goes to Europe and let her stalk me there too.

Two more instances of being asked for help with the subway here. It just keeps happening.

Chicagoans have been distinctly better at recognising my Australian accent – I like the people here.

I leave Chicago a happy little vegemite and ready to head back to the West. Although my preference is firmly with the East, I will keep an open mind. I’ve only got a week left in the States (where has 6.5 weeks gone wow) which I’m splitting between Seattle and Portland. States 9 and 10 coming up!