Even before I had been there (if you can count a 20 hour layover in a city as being somewhere), I always wanted to move to Chicago. I knew it was cold but warmed up in the summer, the food was supposedly excellent and it’s a giant city by a giant lake, which I dig.

Peter’s parents were born and raised in Chicago and Peter lived there for a brief time when he was a baby before moving to San Jose, California, and eventually Austin, Texas. His parents are always telling wild stories about partying and playing music in Chicago – his dad was a professional musician for almost 20 years – and made it sound crazy and wonderful. They also said it was terribly, awfully, horrendously cold and would never move back there because of it. Snow, apparently, is not as dreamy as it looks. Bummer.

I love big cities and (almost) everything about them, really. I love having the option of being around lots of people, and I actually like the noises and weirdness and chaos that goes along with living in a crowded place. Peter, on the other hand, has zero desire to ever live in a big city and doesn’t even want to go to New York City, no matter how many times I tell him how awesome it is. And I get that too, actually.

While I think that living in big cities my whole life (and I would include Austin in that category) has taught me how cool and interesting people can be, when you’re living there you never really get the opportunity to see outside of it on a bigger scale. From just my experience living in Costa Rica and Hawaii for the last 14 months, I feel like I finally appreciate how big the world is and how tiny I am in it, how trivial my problems are (and most people’s problems), and how nature can be way more awesome than happy hour.

But back to the topic.


One Day in Chicago

In our route from Austin to Aruba, we took the most bass-ackwards way possible and flew from Austin to Chicago to Miami to Aruba. And since I had never been to Chicago and Peter’s godmother wanted to pick us up from the airport and take us to dinner, game on!

one day layover in chicago

So what does one do on a 20 hour layover in Chi Town?

Well, first we got dropped off on The Magnificent Mile, where I quickly discovered I could afford nothing and headed to the sale rack at Urban Outfitters and American Apparel (we don’t have those in Maui – boo hoo, I know).

Then, we contemplated going to the top of Willis Tower – formerly Sears Tower – but opted for lunch at Portillo’s instead. I’ve never had an Italian Beef Sandwich with hot peppers before, but damn! That shit is good.

best chicago activities

And since I am generally a fan of activities for small children and tweens, minus anything to do with Beliebing, we headed to Navy Pier to ride the Ferris wheel and giant swings before walking to Millennium Park. By the way, I had no clue it got so freaking hot in Chicago in the summertime. Snap! It’s all that concrete and hot sandwiches, I suppose.

best things to do in chicage

I really, really enjoyed Millennium Park. Sure, it’s touristy and hot and crowded, but we happened to be walking through just as the Grant Park Orchestra was setting up for an open rehearsal for the Grant Park Music Festival. Rad!

what to do in one day in chicagoWe also checked out the famous shiny bean, aka the Cloud Gate, simply because I had to.

best chicago things to do

We also thought about taking an architecture boat tour, but to be perfectly honest, we had already walked at least 5 miles through the city and got a pretty amazing view of the architecture from the Ferris wheel, so we re-hydrated and chilled in the shade by the water instead. Trump has an awesome view, but screw that guy.

one day in chicago

For dinner, we headed to Lou Malnati’s for some deep dish pizza, which was baller and fattening and yum. When in Chicago, eat food.

I would have liked to have seen to The Museum of Science and Industry and gone out for music and drinks while I was there, but overall I think it was a successful layover in Chi Town. Peter asked me if Chicago was at all like New York City, but in my opinion it’s very different. Less involved or something. But I’ll be back, Chi Town. Till next time…

P.S. I would give my (theoretical) left ball for another slice of that pizza. I don’t think it would hurt that much since it’s not actually there. Worth it.