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Chicago: Oh my, I went on a vacation!

For the first time in a very, very long time I went on an actual vacation. I explored! I left my apartment (very big deal). I don't often find the time to get out of Boston and take a break from work, so this was much needed.

My friend, Amanda, and I made a list of all the places we wanted to go to and (after knocking off out-of-country places because I don't have a passport) decided on Chicago. Deep dish. Art museums. Architecture tour. We did it all. We mastered the CTA like we were locals. We even caught a Cubs game before the All-Star Break! Lester gave up 10 runs in the first inning, but hey, it's the Cubs (p.s. this was the first time I was at a ballpark that isn't Fenway!).

Chicago was so much fun. Having returned to Boston, it doesn't feel like I went on a vacation. It all seemed so unreal that I left my home and actually went and saw part of the world! I'm already thinking about my next trip and have a newfound desire to explore more.


We stayed at the Hotel Chicago: An Autograph Collection Hotel, which had a bus stop near it and was an easy walk to many top tourist spots. The hotel was safe, clean, and dare I say it - glamorous.


While we were there, A Taste of Chicago food festival was going on! It was the perfect way to try all different kinds of foods from all over Chicago without having to travel to multiple places. Don't forget to try Deep Dish Pizza (we went to the OG UNOs) and a Chicago-Style hot dog at Wrigley!


Purchase a CityPass or GO Chicago Card depending on what you want to see and visit for the most cost effective option.

  • Catch a game at Wrigley!

  • Take an architecture tour, you won't regret it

  • The Aquarium

  • Skydeck

  • Art Institute of Chicago

  • 360 Chicago (Aka Hancock Building)

  • Navy Pier

  • Magnificent Mile

  • Chicago Ferric Wheel

  • Lincoln Park Zoo

  • Take in an Improv Show at the iO Theater or Second City

Here are some of my favorite photos:


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