My Summer in Chicago Bucket List

Hi! Andrea here. I’m one of the three summer reporting interns at Happenstance. This summer, I’ve not only had a crash course in audio journalism (hello, Adobe Audition YouTube tutorials), but also a bit of a whirlwind introduction to Chicago.
I’m the only non-Illinois native at our Happenstance table of six. While Emmanuel frequented little-known Pilsen bars, I sheepishly bought Lollapalooza tickets because I’ve never spent a summer in the city before. While Madison expertly navigated public transportation, I needed Google Maps whenever I ventured out to do some reporting.
Though Boston will always be the city closest to my heart, I’ve come to know and love Chicago this summer. Here’s a list of some of my favorite Chicago spots and activities!
Architecture Boat Tour
I’ve lived in the Chicago area for two years now without doing anything “tourist-y,” so I felt silly starting this summer. But I ended up having a great time when my parents persuaded me to join them on Chicago’s Original Architecture Tour, offered by Wendella Boats. I was able to slow down and notice the buildings I usually walk past while my eyes are glued to my phone. And I learned a ton about Chicago history that day.
Stan’s Donuts
My boat tour experience was greatly enhanced by the Biscoff banana pocket I bought before boarding for the ride. I have Stan’s Donuts to thank for that perfect donut, full of cookie butter goodness. Whenever my River North reporting took me remotely near Stan’s on Michigan Avenue, I had to stop for a snack break. These donuts absolutely live up to the hype. If you haven’t tried them yet, you’re missing out!
Movies in the Park
The Millennium Park summer film series was a must-see on my summer bucket list. Who doesn’t like a free outdoor movie, especially at such an iconic Chicago venue? I went with a few friends to see “Coco” a couple of weeks ago. I definitely recommend bringing blankets and snacks and arrive early if you want to snag a good spot.
Eataly
I had been to Eataly in New York City before this summer, but the NYC location has nothing on Chicago’s Italian marketplace. I was overwhelmed by the selection of wine, pasta and desserts — but in a good way. I ended up ordering an unforgettable goat cheese and mushroom ravioli at La Pizza & La Pasta, one of Eataly’s few sit-down restaurants. Even though I was stuffed, I found room for salted caramel gelato for dessert. I’ll definitely be going back for a second trip!
Wrigley Bleachers
Confession: I’ve never been to a Cubs game. Baseball isn’t exactly my cup of tea, so my first time at Wrigley Field was a Foo Fighters concert this summer. Not only did the Foo Fighters put on an incredible show, but sitting in the Wrigley bleachers with a view of the city also made the experience that much more special. After that concert, I decided that a baseball game might not be so bad if it’s at Wrigley.
Antique Taco
After hours of exploring and enjoying the live music at the Wicker Park Fest, I wandered into Antique Taco in search of a snack. I can say with complete confidence that the garlic shrimp tacos with elote-style cauliflower and fried kale are the best tacos I’ve had in my life. Aside from its Wicker Park storefront, Antique Taco also has locations in the Loop and Bridgeport.
Navy Pier Fireworks
The Navy Pier fireworks were a twice-weekly highlight of my summer. Though I couldn’t make it downtown every week, I had a view of them from across the lake at Northwestern’s Evanston campus. Every Wednesday and Saturday night, I would try to head out to the Lakefill to watch the colorful display. The fireworks are a summer spectacle that anyone in Chicago can enjoy — and they’re beautiful from any vantage point in or near the city.
Though the summer is coming to an end, my Chicago bucket list continues to grow. I can’t wait to go to a Cubs game and complete some more Chicago firsts (I still haven’t been to the Shedd Aquarium!) in the upcoming year.
In addition to the above spots, I hit other Chicago sites during my reporting excursions, which you’ll hear when the app is expected to launch in the spring! Thanks so much to the Happenstance team for sending me on some memorable adventures this summer!

