Snapshots from My Trip Home to Chicago

Chicago Illinois Trip Recap - Pearl Girl

I always say that if I’m going to live a flight away from my family and childhood friends, I’m glad said flight is NYC to Chicago. It’s fast, it’s frequent, and most important of all, it’s inexpensive (most of the time.) I try to get back a few times a year, but usually, it’s for a long weekend — like four or five days. But over the Fourth of July, I was able to go back for eight days.

This post isn’t a guide, just a recap of what I did during my trip home. (Though there are a couple ideas if you’re visiting Chicago anytime soon!)

Chicago Illinois Trip Recap - Pearl Girl

I landed on Sunday morning and after a nap and a trip to Costco (to stock up on makeup wipes, duh) I met up with a few friends to drive up to Milwaukee for Summerfest. My parents live just north of Chicago, so the Wisconsin border is less than an hour away, and Milwaukee is just a little further than that. I’d only been to Summerfest once before, but if you’re in the area, I highly recommend it. It’s billed as the world’s largest music festival, but it’s more relaxed than something like Lollapalooza or Coachella. There’s a headliner every night, which you have to pay extra to get into, but otherwise there’s lots of artists that you can see perform for just the price of admission. We saw Andy Grammer for $20 and he was great! We were there all afternoon, and had a ton of snacks: Cheese curds, corn, a rib sandwich. When in Wisconsin, y’all.

Chicago Illinois Trip Recap - Pearl Girl

I did pretty much nothing on Monday — we got back home from Milwaukee after 1 a.m., and after an early flight wakeup call, I just wanted to sleep and relax for a bit. I did head downtown for a late drink on my friend’s rooftop — how incredible is her view?!

Chicago Illinois Trip Recap - Pearl Girl

I was all over the place on the Fourth. A barbecue at my friend’s place in the city, a barbecue at my mom’s house in the suburbs, and then meeting friends for fireworks in Evanston, which is a city just north of Chicago. The fireworks were right on the lake, which was so nice!

I didn’t take a ton of photos over the next few days, which involved a trip to the Taste of Chicago, drinks on the Chicago Riverwalk, a day on at work + dinner in the suburbs.

On Friday I met my mom and cousin for lunch at the Hampton Social, which I’ve been dying to try forever. Y’all, worth the hype. We had frosé and I had a lobster roll. I didn’t think Chicago could serve up a good lobster roll — I was wrong. And I finally got to see the Rosé All Day sign in the flesh. They’re opening up another Chicago location soon, too!

I then went to meet up with my friend Emily at her parents’s new place. They recently left the suburbs, but now they have a pool! So needed on a hot day. We got tacos with a few more of our friends after, and then walked around Millennium Park before I caught the train back home.

Saturday was a highlight — a Cubs game with my family! We got lunch in Wrigleyville beforehand and then watched them take on the Pittsburgh Pirates. They lost, which sucked, but I had a Mai Tai and there was a set of back-to-back home runs, so that was something. My grandma is a huge Cubs fan so it was especially great to go to the game with her.

My grandma loves Kris Bryant, who plays third base for the Cubs. So when we saw this mural Call her, KB! She’s your number one fan.

It was such a great trip. And it was long enough that at the end, I was really ready to head back to the city. I’m so happy that it lasted a little longer than usual, because I’m not planning on going home again until Christmas. (I am excited to experience Thanksgiving in NYC, though!) It’ll be the longest I’ve ever been away from “home” (in quotes as New York really is my home now.) But that just means I’ll be super excited to go back when I do fly home again!

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