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A Few Days in Chicago

My first time in the Windy City!

In September, Justin and I went to Chicago for my study abroad program's 5 year reunion. We made it an excuse to take a little vacation there :)

We got sooo lucky with the weather where the weekend before we went was in the 90's and the day we left it was raining. It was a nice 70-75° while we were there!

While we were there, of course we had to try deep dish pizza 😋 if you don't know this about me, I loveee pizza 🍕 Justin wanted to try other popular Chicago foods including the Italian beef sandwich and the Chicago style hot dog.

Day 1

The first day we got there, there was a Taste of Chicago food festival going on at Buckingham Fountain which was right across the street from our hotel. So we got to try Lou Malnati's Pizza. It was okay, we only had an option of cheese or pepperoni and it was $7 for a large slice. Justin also tried a Chicago style hot dog there.

We went to Willis Tower/Sears Tower (the 3rd tallest building in the US) and went up to the Skydeck which had a nice view of the city. There's a section there called the "Ledge" where there are 4 Ledges that have a glass floor people can walk on and take photos on. You only get a limited amount of time on the ledge. The times vary by group size, so Justin and I had 60 seconds to be on the ledge and take the photos/videos we wanted. It definitely goes by quick, but we didn't want to get back in the long line to do it again.

Day 2

The next day, we started off with going to the Art Institute of Chicago. We happened to arrive at opening (not planned). We got to see many famous paintings, but somehow missed American Gothic. 🫤Afterwards, we went up north to Pequod's Pizza for lunch. Justin heard it was very good and it was featured on the show we've been watching recently called "The Bear." I was happy I was able to customize the pizza with the toppings I like. I liked it much more than Lou Malnati's, so it is worth the longer trip there. Afterwards, we walked around Lincoln Park which was very pretty and walked around the Conservatory.

Then we went back to our hotel to get ready for the reunion. The reunion was on a boat that sailed along the Chicago river and into Lake Michigan, it was so pretty seeing the skyline at night. It was great getting to catch up with people I hadn't seen in 5 years!

Day 3

On our last full day in Chicago, we went on an architecture boat tour in the morning. We went with Shoreline Sightseeing as they were included in the CityPass we got. It was nice to see the buildings in the daytime as well as nighttime from the reunion. Also, enjoyed getting to learn more about the buildings we were sailing by and Chicago's history. Afterwards, we ate lunch at Navy Pier and walked around and that's where Justin got his Italian beef sandwich at Ciccio Beef. Then we had to get back to our hotel to get ready for a photoshoot I booked for us.

I'm so glad we did a couples photoshoot for our first time in Chicago/the Midwest. I brought my camera with me on the trip, but I did not care for my photos as it wasn't ideal lighting. But these photos turned out sooo pretty! We had Photography by Lauryn take our photos at Olive Park and Wrigley Building and they turned out sooo dreamy! After the photoshoot, we had dinner at Smith & Wollensky right on the river so we had a nice view to end our last full day in Chicago!

The next morning was our flight back home, but we had a great time in Chicago and hope to come back in the future!

Looking back, we'd probably stay an extra full day to do some museums we didn't have enough time to do including the Field Museum, Shedd Aquarium, and Adler Planetarium. Plus, I'd want to go to a Cubs game at Wrigley Field! Will definitely have to get pizza at Pequod's again!

Here are some of our photos from our couples photoshoot!


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