In case you missed it, a few weeks ago I snagged a flight to Chicago for $50. I went to stay with my college roommate, Maggie, who lives out in the 'burbs - and I have to say - if you really want to get a feel for what it's actually like to live in any given city, staying with someone who actually lives there is the way to do it. I got the Chicago insiders' tour, which made my recent trip more enjoyable and interesting than the previous trips I'd made to Chi town.
For starters, I'd never heard of Portillo's. But apparently it's "the place" to go for Chicago-exclusive fast food. I've been told that Portillo's is to Chicago as In-N-Out is to the West Coast. So of course I was in.
I learned that each Portillo's location has it's own "theme," and the one I visited just happened to be 50's diner-themed. I enjoyed my Italian beef sandwich under the glow of neon lights reflecting off chrome interior accents. I will say I'd prefer an In-N-Out Double Double over the Italian beef sandwich, but maybe that's just the West Coast in me refusing to be subdued.
Saturday night we bailed on a White Sox game because of the weather (Chicago, am I right?), so we instead decided to grab some beers and grub near iO Comedy theater so we could bounce over there to watch a college friend perform. If you've never heard of iO, you can think of it as the launch pad for famous comedians like Tina Fey, Chris Farley, Seth Meyers and SO many more. Over my weekend, I actually ended up seeing two shows there. It was pretty awesome thinking that someone I just watched perform could be on the next season of SNL.
Sunday we took the train into the city to explore. We walked the few blocks from the train station down to Millennium Park, because although I'd been to Chicago twice before, I'd never actually seen "The Bean" up-close and personal. So we did the most touristy-thing anyone can do while in Chicago - we took a selfie in the bean.
We then continued our city walk to the coast of Lake Michigan where we could view part of the harbor as well as the Navy Pier off in the distance. I didn't realize how long it had been since I'd seen a goose until I saw these dudes chillin' in the water.
On a whim, we decided to take an architectural river boat tour. It ended up being my favorite part of the trip. A volunteer architect/engineer talks about the architectural styles and engineering features of Chicago's landmark buildings as a riverboat takes you up, and then back down the river. You see the Willis (Sears) Tower from a pretty astounding angle, as well as the Trump Tower, the Boeing building, and the Tribune Tower, and countless apartment buildings that would be sincerely dope to live in. (sorry I said dope).
We then made the hike over to Wicker Park to eat at *ahem* the new BOOZY TACO BELL RESTAURANT. Let me explain myself.
I've been working on the Taco Bell account at work for the past 9 months, so I heard about the boozy Taco Bell from the time of it's inception and did a lot of the PR work around the grand opening. So I figured I HAD to go if I was going to be in Chicago. For those wondering, you can't go wrong with a Sangria freeze and a shot of tequila.
Monday afternoon I finally got my hands on some deep-dish pizza from Lou Malnatti's. I have no photos, I'm sorry I've failed you all. But Lou Malnatti's is where it's at. (If you think someone in Chicago is asking you if you want to eat at Illuminati's, they're not.)
Monday night I felt like a child leaving home independently for the first time as Maggie handed me a timetable for the train with highlighted departures and arrivals. She made me write down her address just in case I got lost and told her to call her when I get there to make sure I wasn't kidnapped.
I met an old friend at iO for another show and we caught up on where we'd been over the past few years. I actually didn't even realize how many college friends I have living in Chicago, and they all (luckily) came out of the woodwork while I was there. (It was so wonderful to see you, Ashley, Joe, Cat, Sarah, Jessie and Marc!)
Tuesday was the real test of my adult-ing abilities. I was working out of my company's offices in the city, so I had to ride the commuter train in and walk to my office from the train station. I managed, and I was even on time! My whole workday I was graced with an amazing office view. I met one last friend for lunch, wrapped up my workday and then headed for the blue line station.
I rode the train underground in the darkness below The River District and then watched out the window as Wicker Park, Logan Square and Irving park passed by in blurs. Four days in the chill of a Midwest autumn is just what I wanted, and seeing old friends while making new memories was exactly what I needed.
See more photos from my trip here!