Two Days in Chicago, IL

This summer, my boyfriend and I visited Chicago — the windy city or, as I like to call it, “Smaller, Cleaner New York.” I wanted to share our packed itinerary (I’m all for doing as much as possible during a trip) and make some suggestions!

We touched down in O’Hare on Friday morning in late August, and took a cab ride into the city. We had a nice view of the skyline for most of our drive, and I was pretty fascinated by the subway that ran right along the middle of the highway. We drove through the city, and saw some of the sites (a few gigantic murals, that store with the barbecue sticking out of it, and the biggest McDonald’s in the world — my boyfriend was very excited about that last one). We stayed at the AC Hotel Downtown, which was a very nice but basic hotel. It was extremely modern and gray, which is not my aesthetic at all. The artwork on the wall was literally a photograph of an empty gray concrete room. But I can’t make any further complaints because the bed was comfy, the room was spacious, and the service was excellent.


We were a little exhausted from the plane ride, so we decided to grab a refreshing lunch at Carmine’s. This place was SO good. We sat outside and had bread dipped in olive oil, fresh caprese salad, and the famous brick oven thin crust pizza (with meatballs on top). We also wanted to try the famous jumbo cakes slices, but were too full. This is such a sweet, romantic lunch or dinner spot. I definitely recommend it!


Next, we decided to take a long walk. My boyfriend and I are firm believers that the best way to see any city is to just walk. Since Carmine’s is right near the water, we headed east to stop at Crescent Beach. I am weirdly drawn to bodies of water, so we spent a lot of time walking along Lake Michigan. I was really shocked by how BLUE the water is — like the Caribbean! We also checked out some of the art murals, and general architecture of the city. We stopped to buy me a dress for dinner that night, and then walked back to our hotel.


For dinner, we ate at Art Smith Blue Door Kitchen with friends. The food was all farm to table, and the atmosphere was very quaint and Southern. We ate upstairs in a room filled with antiques, plates hanging on the wall, and amazing wallpaper. It reminded me of the Olde Pink House in Savannah. For food, we got eggplant puree pierogis, kale salad, root vegetable salad, purple gnocchi, mac and cheese, and corn — all delicious. For dessert, we walked to “Viagara Triangle,” so-called because of the old nightlife scene there. It’s actually a cute little park now with a fountain and lots of seating. There was a gelato stand, and I tried a scoop of the blueberry french toast. My boyfriend, of course, stuck with vanilla (his all time fave). We went back to our hotel, and fell asleep immediately.


The next morning, we met up with friends again for breakfast at Eggsperience. I had the whole wheat pancakes with sugar free syrup and strawberries. Their orange juice was unbelievably amazing. We stopped back at the hotel quickly after breakfast, and I ran into an old co-worker from one of my internships back in New York. It was such a weird coincidence. We did a quick window shopping session, and then walked to the Art Institute of Chicago. This was a somewhat distant walk from our hotel, so we got to see even more of the city. We spent most of our afternoon there — I was shocked by how large the institute is. I’m kind of an asshole New Yorker, so I assumed that it would be small. My boyfriend and I were a little underwhelmed by the pre-18th century collections, but we were very impressed by the amount of true, quality pieces that they have: American Gothic, The Nighthawks, a handful of beautiful Magrittes, Cranach’s Adam and Eve, Caillebotte’s Paris Street, Suerat’s Grand Jatte, and many others.



After the museum, we walked to Millennium Park to see the Bean! Lots of people and lots of fingerprints, but it was so good to see it in person! It really is a remarkable piece of public art that achieved iconic status, and it reflects the skyline beautifully. To end our trip, we got deep dish pizza at Giordano’s. My boyfriend and I agree: deep dish pizza is not pizza. It is tomato and cheese pie. But it is absolutely delicious. Well done, Chicago! We got a nightcap at our hotel bar, and flew back to New York the next morning.

I really loved Chicago, and I’d like to go back soon. Thanks for reading!


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