Weekend Getaway: Chicago


This Christmas, my parents surprised my sister and I with the best present I have ever been given: tickets to see the Tony award-winning musical Hamilton showing in Chicago! This July, we flew to the beautiful Windy City for a long weekend. I had been to Chicago once before, about 11 years ago. Needless to say, I didn’t remember much of it, but it did not disappoint.

The City

I had some reservations about Chicago before I arrived, simply because I had heard of it having a dangerous crime rate; however, I never experienced anything that made me feel unsafe. Chicago is a BEAUTIFUL city! I was obsessed with all of the tree-lined streets and people walking their dogs. The architecture was so pretty. I quickly realized that this city is often displayed negatively when, in fact, it is a great place to spend a long weekend!

SkyDeck Chicago

SkyDeck Chicago is the place that has the glass floor you can walk out 103 stories high! I thought I would be able to handle it no problem, but I got extremely nervous when I finally got out there. It is definitely something you must do once in your life, no matter how scary! The wait line wasn’t terrible, and they have interactive displays to look out throughout the line!

The Bean

The Bean in Millenium Park is so cool! It literally is a giant bean right in the middle of a park. It is something you must see if you’re ever in Chicago!

The Magnificent Mile

The best place to shop! The Magnificent Mile has all of your favorite retail stores and great restaurants around. The whole area is perfect for a first time visitor!


The Food

Oh-em-gee. Chicago is full of so many amazing restaurants and cafes. Being the foodie I am, I made a list of all of the restaurants we had to visit during our stay.

Chicago Pizza & Oven Grinder Co.

Have you ever heard of the Pizza Pot Pie? If not, look it up right now! I wish I would’ve taken a picture of this dish. The Chicago Pizza & Oven Grinder Co. was by far the best place we visited. We started off with a salad appetizer, and finished off with the amazing Pizza Pot Pie. I preferred mine with meat and no mushrooms, but it’s very customizable to fit anyone’s taste! The doors open at 4, and I suggest getting there much earlier to get in line! We arrived at 4:04pm and had a 45 minute wait! It was definitely worth it.

Margie’s Candies

This is the hidden gem of Chicago. It’s a little farther out than everything else downtown (a 20 minute Uber ride) but so worth it. This is one place we ate dinner at in the early afternoon, that dinner being a 6 scoop ice cream sundae! Margie’s is a small shop, but they offer a great old-time charm. The ice cream itself was delicious; it was even better with the hot fudge and strawberries we added on top! I highly suggest visiting this awesome establishment.


By far the best part of the trip, seeing Hamilton was a dream come true. I have been a huge fan of the show since the soundtrack was released in 2016. The stage was so beautiful and the actors didn’t disappoint! I hope that the show eventually goes on tour so everyone can have exposure to this great experience!


Chicago was a great place to visit on a long weekend. Our schedule was packed, and we got in as much of the city as possible. If you’re looking for your next weekend getaway, I highly suggest visiting the Windy City!

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