Chicago, IL

It’s been about a month and a half since I visited Chicago, so now I’m going to tell you all about it. I took a Lyft to Logan Airport and got there with plenty of time to spare, so I got some Dunkins like the good New Englander that I am. I got to Midway Airport at about 8 AM. Once I figured out the subway card, I made my way into the city. First stop–Intelligentsia.

I got my coffee and walked over to Millennium Park to see the bean. I walked through the park a little more then headed over to the John Hancock Center observatory. Since it was still fairly early, there wasn’t any wait at all. The day was clear so the views were pretty.

From there I walked around the Financial District for a bit, stopping for lunch at Chick-fil-a, ha. Then I went over to the Lincoln Park Zoo, which is free and wonderful. I spent a good amount of time there, and once I found the hippos, was content in leaving.

After the zoo I walked around the conservatory for a bit, which is also free. By that time it was getting close to check-in time at the hostel, so I walked over and did that. I stayed in a dorm-style room that had eight bunk beds. I was assigned a top bunk, which I wasn’t too crazy about, but the climb in and out of bed wasn’t too bad, and I didn’t fall or anything, so that’s good. After resting for a little bit, I took the subway and met Anna-Marie and her boyfriend, Chris for dinner at Lou Malnati’s. And that was day one.

I started day two early by going on an architectural boat tour. It was relaxing being on the boat and floating along the river, passing all the buildings and learning their history. After the tour, I walked over to Navy Pier and hung around there for a bit.

From there I took the bus over to another Intelligentsia location, but when I got there, I learned that they were closed. So I went over to Willis Tower (formerly Sears Tower). When I arrived, I found an angry crowd of people who weren’t being let in. The tower’s elevators had broken down, so they were only letting people in if they had bought their tickets before the day of. Fortunately, I had bought mine at the hostel the day before, so I was let right in. It was still an hour wait, and then we had to take the service elevator up, but I finally made it to the Skydeck. My plan was to just take selfies, but anytime I would try to, someone would offer to take my picture for me, so I’d let them. That was nice. I spent a long time up there since I had waited so long to get in.

Once I left, I realized that I hadn’t really eaten anything all day. I wanted to try deep dish pizza from somewhere other than Lou Malnati’s, so I ordered one for pick up from Pizano’s Pizza. Deep dish pizza takes so long to cook, so I killed time in Target. I figured I’d get my pizza, walk over to the park, and find a nice patch of grass to sit in. Deep dish in hand, I headed over to Millennium Park.

There I found tons of people, and discovered that I had walked right in to the (free) Chicago Jazz Festival. I found a little spot way up in the front and ate my pizza whilst listening to jazz. It was wonderful. After that, I went to Starbucks to buy a souvenir mug. Then I walked around the mall a little, and also visited Eataly. By that time, I was pretty tired, so I headed back to the hostel to refresh. I figured I’d relax for a bit and go back out to explore. I did not. I ended up hanging in the common area, reading, which was pretty nice.

Day three was my last day in Chicago. I got up early, packed up, and checked out. I took the bus to Old Town and of course, went to Intelligentsia. I had a nice morning drinking the most wonderful cold brew and reflecting on my trip.

Once I had done enough reflecting, I walked over to the Chicago History Museum. I was one of the first people there, and there weren’t many of us anyway, so I got to take my time through the non-crowded museum.

When I was done there, I stepped outside just as it started pouring rain. I waited for a bit since I didn’t have an umbrella, and it lightened up a little. I went over to A New Leaf, and hung out in there for a bit.

Then it was time to head over to Wrigley Field. I love being near baseball parks. The energy and the camaraderie amongst fans is so exciting. I was also glad to get to visit the park. It’s the second oldest active ballpark, Fenway Park being the first. It’s like stepping into baseball history. I checked my backpack and waited for Anna-Marie and Chris to arrive. The game was really good, and the Cubs won, so that was cool.

From there we got onto the very crowded subway. I made a pit stop down by the Loop to see the Chicago Theatre, then I headed to the airport. Anna-Marie told me to be sure to get a cheese and caramel popcorn mix–apparently it’s a Chicago thing, called the Chicago mix–so sure enough, I found a Nuts on Clark in a terminal, and I was glad I did.

And that was my trip. I felt so empowered exploring the city all by myself. Chicago has beautiful architecture. I’m glad I finally went. Up next will be recaps from my sister’s visit to Boston, my visit home, and my trip to Toronto with Summer.

One thought on “Chicago, IL

  1. Your trip sounds wonderful! I love reading about all of your travels. I think it's impressive that you're not afraid to venture out on your own. Can't wait to read the rest of the recaps!

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