Road Trip: Sweet Home Chicago

Posted by Ruth Brown on July 8th, 2011

photo by D-J-C on Flickr

So Monday the other week, I’m checking out waterfalls in Columbia Gorge with my parents, when I get an SMS from The Boy saying he had to go on a last minute trip to Chicago on Thursday and did I want to come? At first I thought no, because I’d had a big week doing stuff with my folks and was going to San Fran the next week and Las Vegas the week after, but my parents were all “Are you fucking crazy? Go to Chicago!” (Except with less swearing, because they are not crass like I am and my mother does not know where she went wrong with me) so I said yes.

It was a pretty short trip, though, so I basically had a day and a half to enjoy the city.

I went into Chicago with very few expectations, which is the best way to travel if you can. It was impossible for cities like New York or London, but what did I know about Chicago? Well, the musical Chicago. The Blues Brothers. Dirty Chicago politics, I knew. And Obama.

I have a bit of a formula for finding things to do when visiting cities. The first is the New York Times’ “36 Hours in…” columns then TIME’s 10 Thing to Do in 24 Hours, then I find the local alt-weeklies (which tend to write up less touristy things to do), then I check Yelp and Chow to find places to eat (it’s easier to plan ahead when you’re a vegetarian).

After perusing the options, my vague plan was “art, architecture and food”. That is basically what went down.


My first stop was the Art Institute of Chicago. I think I planned on spending an hour or so there, but ended up staying way longer — pretty much the entire afternoon of day one. I hadn’t anticipated quite how amazing the collection would be, and I felt obliged to go into every room, lest I miss some really important piece of art and have to live the rest of my life just a litte bit less cultured than I might have been. I think the best thing I saw was Chagall’s America Windows.

The next day, I went to the Museum of Contemporary Art, where, amongst other things, I saw Eiko & Koma writhing around on the floor naked. The bathrooms had speakers playing people making weird noises, which was a bit much. I’m all for weird-arse art, but not when I’m urintating, thankyouverymuch.

This is not the naked Japanese performance artists. I thought it would be creepy to photograph them, though others were.

I wish I’d had time for more. Others recommended the Field Museum and the Planetarium, which both looked cool.


Staring at buildings may sound boring, but the architecture in Chicago is just amazing. The Chicago Loop is serious sore-neck territory. I like big cities and I like big buildings and I could probably have spent a whole day just wandering around gawking. But I did not have a whole day, so I contented myself with just staring at them in between other things. It’s a truly attractive city.

I didn’t actually do an official tour or do any research, so I can’t tell you shit about the buildings I saw or what they were called.

I spent an unanticipated amount of time in Millenium Park, which is next to the Art Institute. It’s weird to be in a city that isn’t totally skint again, where they build big, impressive things just for people to see and use and for the sake of being pretty. Case in point: the Gehry-designed Jay Pritzker Pavilion is very impressive and a beautiful place to sit and watch a show. Some band was rehearsing — it was a bit jazz fusiony for my tastes, but a lovely way to kill time nonetheless. Also: free.


One thing I try to do in a city is get out of the downtown area to where people actually lived. My friendly local barista, a former Chicago resident, gave me some suggestions on where to head, so on day two, I caught the train in the general direction of the general Wicker Park/Bucktown area. I got off around the Ashland/Division/Milwaukee intersection (for those who know the city). It was a far cry from the pretty buildings in the city. Based solely on observation, the area appeared to have large Mexican and Vietnamese communities. I had heard Chicago had good Mexicana and I hadn’t had breakfast, so I Yelped it up and was informed a nearby grocery store had a good taqueria hidden inside. Sure enough, round a weird corner in the store was a bunch families eating tacos. The taquerias I saw tended to have more focus on tortas than those on the West coast, and less on burritos, which makes sense, as the latter is, for all intents and purposes, a West coast invention. Tortas are huge Mexican sandwiches made with big white rolls and fillings not dissimilar to what you’d find in a burrito (minus the rice) — refried beans, avocado, crema, salad, jalapenos, various meats. Terribly unhealthy, but entirely delicious. This was a good one (I got no meat, but extra beans) and cost like $3 or something ridiculous. As I walked further into the area, eating my torta, it got¬†increasingly¬†gentrified and bland, but I liked that bit — still a bit grimey and grungy.

There was only one thing I absolutely had to try in Chicago, and that was a deep dish pizza. It’s famous and you don’t really see them elsewhere. I went to a Lou Maltnati’s, because it was close, seemed to be fairly well regarded, and did individual 6″ pizzas to go. It is essentially like a pie — with the pizza base shaped into a crust, and the topping as the filling. I love a great pizza crust and this was not one. However, growing up on unremarkable suburban Australian pizza, I have always been of the opinion that if the crust doesn’t have much going for it, it should just be covered in topping. Deep dish pizza is like the ultimate pizza for topping lovers, because you get about three times as much for the same amount of space. I think it is a wonderful thing and I don’t understand why it hasn’t spread further.

Summary: Chicago exceeded my expectations. Which is easy when you have none. But seriously, it’s a cool city with a vibe that says “Hey I’m happening and important but a bit more digestible and down-to-earth than New York”. I give Chicago a B+.