Chicago, Twice: A Language School Summer and a Winter Return

Summary

In 2015 I decided to spend a month in the US, splitting my time between traveling and a language school. I picked Chicago because a good friend’s sister was living there and offered to help me get set up with a homestay. I flew out on my birthday that year and ended up staying about three or four weeks. I went back in the winter of 2019 for less than a week. This post pulls from both trips, so some of it is summer and some of it is winter, but it’s all the same city.

Table of Contents

Pier Park and Chicago's Caramel Popcorn

I went to Pier Park at Navy Pier with one of my housemates in 2015. Neither of us spoke much English yet, but we had a great time anyway. At one point we wandered into a popcorn store selling what felt like a thousand different flavors, which threw me off completely. In Turkey, popcorn is salty, and I wasn’t a fan of sweet popcorn going in. Then I tried the caramel corn and completely changed my mind. It was that good. I’ll say this, though: not every sweet popcorn in the US is worth it. That one just happened to be.

Michigan Avenue: A Gothic Church, A Three-Floor Starbucks, and the Apple Store Where I Got My First Apple Watch

Walking down Michigan Avenue was the moment Chicago felt like a real metropolitan city to me. The buildings alone were worth the walk. At some point we wandered into a church almost by accident, and the inside stopped me. Gothic architecture is something I fell for while I was studying in Paris, where it’s everywhere, so finding it again in Chicago caught me off guard in a good way. After that we stopped at the Starbucks Reserve Roastery nearby, which has three full floors, and later swung by the Apple Store on Michigan Ave for a pair of earbuds. I’m still using them today.

Millennium Park, the Bean, and a Lollapalooza Ticket Off Craigslist

Seeing the Bean was non-negotiable on my first Chicago trip, and it’s exactly as touristy as everyone says. Everyone wants their photo there. Nearby was a piece I liked even more: Jaume Plensa’s giant head sculpture, “Looking Into My Dreams, Awilda,” which was on display in Millennium Park that year.

Once I landed in Chicago, I checked what was happening around town and found out Lollapalooza was that weekend. I didn’t think twice. My English wasn’t good enough yet to navigate ticket sites on my own, so I asked my friend’s sister to help me find one on Craigslist, and somehow it worked out. I got a three-day pass. I was going alone, which worried me a little, but I ended up going with a group of friends I’d met at the language school. It was chaotic and I was completely unprepared, but it was worth it. I heard later that Lollapalooza in Chicago got canceled for a year not long after, so I’m glad I caught it when I did.

The Chicago River, Smith & Wollensky Steakhouse, and Chicago Theatre at Night

The Chicago River is worth seeing just for how it cuts through the middle of the city. It reminded me a little of the Seine in Paris, though the energy around it is completely different. 

One winter night in Chicago, I had dinner at Smith & Wollensky Steakhouse right on the river, which felt like a proper American steakhouse experience, and I loved it. 

If you have the time, walk down State Street at night to see the Chicago Theatre marquee lit up. It looks like something out of a movie.

Willis Tower Skydeck at Sunset

I went up to the Willis Tower Skydeck in 2015 with a few friends from the language school. The timing worked out perfectly, we got there close to sunset, and the view over the city was incredible. There’s also a section with a glass floor, The Ledge, that lets you step out over the edge of the building. Of course we tried it.

Christkindlmarket at Daley Plaza: A German Christmas Market in Chicago

We also stopped by Christkindlmarket in the winter of 2019, and it’s one of my favorite memories from that trip. It’s a proper German-style Christmas market set up right in Daley Plaza, and just walking around it, it hit me that most of what we think of as classic Christmas traditions, the markets, the ornaments, the whole calendar of it, trace back to Germany. I bought a Christmas mug and some chocolate while I was there. It’s the kind of place that’s genuinely fun to wander through, just taking in the lights and the holiday atmosphere.

See what I've been up to in my Latest Posts!