Travel • 

Three Days in Chicago—What We Ate + Admired

By Renae Hilary

A few weeks ago, we flew to Indiana to visit my brother, Warren. Because it was his birthday and because we’d never been, we decided to spend three days in Chicago. It’s only a four-ish hour drive from the small town where Warren lives. For Californians like us, it’s a novelty in itself to get from one state to another so quickly. We packed up a rental car (we as in my mother, Adam, Warren, and myself) and drove past cornfields that seemed endless, broken up only by rows of windmills and storybook red barns. This is the Midwest, I reminded myself as we drove. Something about being there made me want to drop the cool cynicism I brought with me from Los Angeles. 

Chicago is the Midwest, too—the major metropolitan, cosmopolitain hub of the Midwest. Once dubbed The Second City by a famous journalist, it’s often categorized as a friendlier, more approachable version of New York. Not quite as developed, not quite as happening. If Chicagoans resent this silver-medal status at all, they don’t show it. Yes, Chicago reminds me of New York. But it has a hardworking, straightforward, uncynical vibe that is distinctly Midwestern. This is a city that reestablished its greatness after burning to the ground for three days in The Great Chicago Fire of 1871 and again after being ripped apart by gang violence and corruption during Prohibition. 

I felt the city’s ingenuity in everything we did there—from those proud, Art Deco buildings with their geometric details and glamorous ornamentation to the deep dish pizza, equally impressive in its architectural merits. Yep, Chicago makes awesome things. As a follow-up to that lofty statement, here’s a list of some of those awesome things we experienced during our long weekend there.

Millennium Park + Grant Park
At Millennium Park, we found a buzzing crowd of people that just looked grateful to be outdoors (perhaps this attitude has something to do with Chicago’s brutal winters). Despite the thick humidity, people danced with abandon to the jazz band playing Stevie Wonder and Michael Jackson covers. From there, we walked down to Grant Park to watch the sun set over the boats docked int he harbor. It was one of those moments that made me feel happy to be in a city, lucky to be a part of this community for the moment.

The Theater District
I have a thing for old theater marquees, with their flashing light bulbs and carnival-esque primary colors. I like their proud spectacle of old-world glamour in the midst of more austere, contemporary structures. Serendipitously, we spotted The Book of Mormon illuminated on one of said marquees in Chicago’s Theater District. Perhaps I’m a few years behind in advising you to go see it, but do if you haven’t already.

Wendella Boat Tour
On our second day, we cruised through the three branches of the Chicago River on the city’s requisite architecture tour. Out of the whole skyline, those chic, over-the-top Art Deco structures won my heart. But the 108-story Willis (formerly Sears) Tower is the second tallest building in the US… so, you know, I guess that’s impressive too.

Giordano’s
Reader, I will spare you the photos of our deep dish pizza (and the Chicago dogs we ate at Portillo’s for that matter). Like most foods that are unapologetically heavy and stuffed with other foods, it doesn’t have too many flattering angles. Indeed, I’m guilty of judging a pizza by its cover because I certainly didn’t expect to like this audacious, hot mess of a dish. Yet, those layers of thin, chewy dough, perfectly gooey mozzarella, and a surprisingly delicate pizza sauce melted my skepticism right off. 

Eataly
I will, however, show you some of the sexier images from our meal at Eataly. We had Warren’s birthday lunch at the Chicago location, and it was perfect. The crisp white wine, the paper-thin charcuterie, the pasta that somehow always has the perfect amount of snap and chewiness—this, friends, is what they call good living. More on Eataly in this post.

The Art Institute of Chicago
Yes, Chicago makes awesome things. But they collect awesome things, too. The Art Institute has so much good stuff, including a beautiful Georgia O’Keefe gallery. And their Impressionist and Post-Impressionist collections are so vast, they reminded me of being in the Musée de l’Orangerie in Paris. Monet, Van Gogh, Degas—the gang’s all there, including a stunning collection by Toulouse-Lautrec, with whom I’m strangely obsessed.

The Little Goat
I say this with a little guilt. The Art Institute of Chicago’s dazzling collection impressed me. But. The Little Goat’s sesame-cheddar biscuit with pork sausage and runny eggs may have been my favorite part of the whole trip. (Sorry.) That sumptuous, fat-on-fat combination of egg yolk and pork fat is enough to weaken my knees any day. Cut with the lip-puckering tartness of ripe blackberries and the earthy, garlicky heat of sesame-chili dressing in this dish, though, it showed me a new level of nirvana. The sweetness-plus-acidity-cutting-through-fat kind of nirvana.

Just in case you’re wondering about the burger, it was Adam’s, and it had all sorts of fun things like bacon, kimchi, and that runny egg you see on top. Not so sadly, I was too absorbed in my own dish to tell you anything about how it tasted. But he recommends it.

Until next time, Chicago. 

More Articles
  • Travel • 

    How was Italy? Well, reader. All the things. All the things you’ve already heard about Italy. The architecture! The art! The carbs! Italy captures people. I can see, now having been there, how one can leave drunk and high off of the physical and edible beauty. It’s dazzling, honestly. And…

  • Food • Travel • 

    When it comes to carbohydrates, there are two distinct categories of people. There are the nonchalant carb consumers, those who prefer a nicer cut of meat or a good vegetable to anything starchy. Then there are the people with actual souls (just kidding… or am I?), the enthusiasts (a.k.a. me, the…

  • Travel • 

    I like attending other people’s graduations. The shot of optimism and “you can do it!” encouragement is always a refreshing change from the cool cynicism of the places I generally hang out (in recent-graduate speak, I think those places are called “the real world”). Two weeks ago, Adam and I…