This past summer, I was given the opportunity to visit one of my college besties, Hannah Hippensteel, who lives very close to the city of Chicago. I’d never been before, and it turned out to be one of the most fun trips I’d ever been on outside of Minnesota.
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To commemorate my brief city-slicker experience alongside my (short) partner in crime, here’s an itinerary of our little adventure that any first-time Chicago traveler can follow.
Wednesday
Upon my arrival to the O’Hare International Airport (thank God I survived!), Hannah and her grandma picked me up and showed me around her hometown of Villa Park.
For dinner that night, her parents treated us to deep dish pizza at Giordano’s, which were the best two pieces of pie I’ve ever had in my entire life.
Thursday
Today was the day designated to explore the great Windy City (which, by the way, wasn’t windy at all).
Before we set out, we ate a hearty lunch at Portillo’s. Even though I’m generally a picky eater, I made it a goal to try a Chicago style hot dog… it could’ve used some ketchup (kidding), but it was delicious nevertheless!
After navigating the “L” public transit safely and being asked by a stranger if I was related to Paris Hilton (spoiler: I’m not), Hannah and her friend Jess guided me through the city, taking many pit stops along the way.
The first tourist site we visited was, of course, The Bean at Millenium Park. I’d always seen pictures of the “Cloud Gate” structure on other people’s Instagrams, but it was a totally different experience to see (and even touch it) in real life.
From there, we walked over to Crown Fountain, a huge public sculpture on which videos of random people’s faces are shown and often spurt out water, and then to Grant Park for Taste of Chicago. There were tons of great street performers jamming out, and the three of us decided to get a small piece of cheesecake as we made our way past Buckingham Fountain.
To get the best view of the city skyline, we made our way to Lincoln Park, taking a moment to rest for a few minutes at a beautiful nearby park and the zoo’s overlook bridge.
After a little shopping (I scored a cozy sweatshirt and a cute magnet for my mini fridge), we concluded the night by visiting the almighty Skydeck in the Sears/Willis Tower. I’d like to point out that I’m deathly afraid of heights (and still am), but taking those few steps forward and gravitating in an observation box over 1,300 feet in the air was at the (literal) top of my must-do list for this trip.
And they aren’t kidding when they say the view is spectacular!
Friday
Today was much more relaxed, as we were recovering from our very busy day prior. Hannah and I did, though, get dressed up and had brunch at a cute restaurant called Simon’s. We both got chocolate chip pancakes, and I could’ve easily had another plateful because they were to die for.
Later that night, Hannah’s dad treated the two of us and her younger sister, Zoe, to sushi at Sushi Nest. I had just tried sushi for the first time a mere two months before with Hannah herself, and I wasn’t sure what flavors I’d jive with the best. Hannah made sure I tried a few different kinds of rolls, though, and in the end I absolutely loved the Spider Roll (no insects were harmed in the making nor the consumption).
Saturday
It was so hard to say goodbye, but I was ready to come back home—I missed my kitty!
Before dropping me off at the airport, Hannah’s grandma treated us to donuts from Dunkin’ Donuts… I know it’s not technically a Chicago landmark or anything, but I’d never been to a Dunkin’ Donuts before, so it was a nice pre-game to another trek through the O’Hare International Airport (which I, again, survived without a single scratch).
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I can’t wait for many more adventures with you by my side, Miss Hannah Marie—love you!