During a cold December night this past winter break, I was FaceTiming my boyfriend Riley at 1:00am from halfway across the country. Lying on my stomach, I listened as he brought up the idea of going to Chicago during spring break; a city I visited back when I was seven or eight years old but have little recollection of.

Indulging him, I looked up a few of the city’s attractions and said, “The big thing I want to do is go to the Art Institute of Chicago.”

He replied, “Only if I get to take you to the Shedd Aquarium to see the penguins.”

We went back and forth about it for about an hour and, somehow, a tentative itinerary locked into place. Two days later, he sent me the link to a cheap Airbnb just outside of the city. Another day, and we paid for three nights of the week.

We anxiously awaited the next two months, and in the meantime, we looked up more exhibits and attractions, aesthetic eating locations, and what clothes were “Chicago-worthy.” I’m an avid planner and it’s nice that my boyfriend and I were on the same wavelength of keeping busy but also having enough time to sit and relax. It made planning our trip so much smoother and more efficient.

Finally, that Monday morning rolled around. We lugged our bags into the trunk of his car and set off on our first trip as a couple!

The three-and-a-half-hour drive flew by as we listened to various artists from Gracie Abrahams to Quasimodo (if you know anything about either of those artists, you know how chaotic that car ride must have been!). When we arrived in Chicago, our first stop wasn’t the Airbnb but the Art Institute of Chicago. We parked using the app SpotHero (this was an absolute lifesaver when it came to Chicago parking) and we happened to emerge from the underground ramp right in front of the museum.

Cold, stiff, and amazed by the windy city, Riley led me into the museum. Inside, we got to see an entire gallery devoted to Claude Monet, the wall of George Seurat’s most famous painting, Sunday Afternoon, hallways of sculptures dating back 5,000 years ago, and my personal favorite, a pile of candy by Felix Gonzalez-Torres that made me gasp so loud that Riley came running back in confusion by how star-struck I was to see one of my favorite pieces in person. Something else my wonderful boyfriend surprised me with were tickets to see the museum’s exclusive Dali exhibit with some never-before-seen paintings and sculptures completed by the artist.

The entire museum was unlike anything I’d ever seen, and we would have stayed longer, but the rumbling of our stomachs was getting a bit too distracting. Almost at closing time, we left the museum and moved on to dinner.

We drove into Wicker Park and ate at the Kennedy Rooftop, a rooftop restaurant that overlooked the Chicago skyline. It was so dreamy to see the sky darken and all the lights within the skyscrapers slowly come to life. We devoured our meals, and the most memorable part was the 1-pound brownie we got for dessert. We were way too stuffed to finish it though, so we packed it up and took it home with us to pick at over the next couple of days.

Exhausted and ready to rest our feet, we arrived at our Airbnb, got into our bathing suits, and hurried outside, shaking from the cold. Outside, a hot tub had been reserved for us and it was the perfect way to end the day. Well, that, and the midnight Taco Bell we ended up DoorDashing as well!

On Tuesday, we woke up early and got breakfast at Wake’N’Bacon which had some of the cutest decors I’ve ever seen in a coffee shop. Slurping down our coffee and devouring some chicken and waffles, we finished in no time and hurried to the Shedd Aquarium. Inside, we were surrounded by thousands of fish species from across the world, pools of starfish and sturgeons that you could touch, and Riley’s favorite, a massive penguin exhibit that we spent wayyy too much time looking at.

Once we saw everything, we still had two hours left with our parking, so we took the Chicago Riverwalk down and saw Chicago’s most famous attraction: The Bean! After way too many pictures, we did some light grocery shopping, hauled everything back to the car, and went to Kyuramen, a delicious ramen place located in the heart of downtown Chicago.

Riley and I chose this place not only for its mouth-watering menu but also for its unique seating! We lucked out that we got the middle section and, I have to admit, this is one of my favorite pictures from the trip. I love how everyone around is in their own bubble with completely different things happening in each booth. Maybe it’s the writer in me, but something about it just seems so poetic! Once we were too full to take another bite, we headed back to our Airbnb and spent the night once again in the hot tub and enjoyed some much-needed relaxation.

Since we didn’t have any planned events for Wednesday, we slept in and got breakfast at Riley’s favorite coffee chain in Chicago called Yolk. The coffee ran smooth, the breakfast sandwiches packed a punch, and we got a great spot right by the train tracks where we could see the trains running back and forth along the rail.

Afterward, we burned off those calories by walking the Magnificent Mile and seeing the Chicago River dyed green for St. Patrick’s Day. Of course, I forced Riley to be my photographer and take cute pictures of me before I dragged him into the Starbucks Reserve to check out all of the coffee smells inside.

As we roamed around some more, we happened to stumble upon the Museum of Contemporary Art. Since we’re a bunch of museum junkies, we just had to go inside and explore. We saw this amazing bubble sculpture which was one of my favorite pieces in the museum! We spent so much time inside that we ran late picking up the car, but thankfully, we were still able to leave the lot!

Back at the Airbnb, Riley cooked dinner for me (it was his idea, I promise) and we sat together, reminisced about our trip, and shared too many laughs over the table. It was an intimate way to spend our last night in Chicago and was such a memorable experience for both of us to see how the two of us work in the kitchen.

Thursday morning, we left our Airbnb for the last time, got breakfast at a cafe called Honey Berry, and ate the best hashbrowns in the world. Our plan to go to the Navy Pier was, unfortunately, curb stomped by the incoming snow, but as we started our drive back to Iowa City, we agreed that we’d definitely come back in the summer to check it out in better daylight and with a new itinerary in mind.

We rolled back into Iowa City around 5:00pm, unpacked, and immediately DoorDashed some food. We were excited to be back, but even more excited now that we had a couple days to relax before classes started back up again. Of course, there was still some homework to worry about, but for that night, it could wait.

Overall, my trip to Chicago had to be one of my favorite trips of all time. It was a mix of exciting and relaxing, refreshing and invigorating. I was so lucky to spend that time with my best friend, and we loved the city so much, that we actually just bought Lollapalooza tickets to go back in August and see some of our favorite artists play live. Our next time in Chicago will most definitely be a blast, just like this was!

I hope the rest of you reading this also had some memorable spring break experiences (parents, maybe you’re reminiscing about some of those old college trips you did back in the day!). Whether you were at home or in a far-off place, I hope you guys enjoyed yourself, and thank you for taking the time to read about my trip!