Travel Diary | Chicago, Illinois

Ever since I was a little girl, I dreamed of visiting Chicago one day. I always thought of it as a more sophisticated and less cliché version of New York City, which to be really honest, I think it was a pretty accurate prediction on my part. 

So this summer I was browsing around airline fares, trying to find cheap flights to New York and finally watch Matilda (which was my favorite movie as a kid) on Broadway. But the fares were so high! That's when I started to look for alternative places to visit, and found some reeeally cheap flights to Chicago. So I took my mom and sister with me and checked one more thing off my bucket list! 

So let's skip to the fun part, shall we? 


Chicago's Early September Weather = Perfection

First of all, as you will see in the pictures bellow, the weather was perfect, to my surprise. I was scared about the whole "Windy City" scenario, but Chicago welcomed us with a comfortable 70-75 degree weather and bright sunny skies. My hair was also digging it. 

The thing that I loved the most about its streets was how clean everything looked and all the fresh air that came from the Great Lakes. It was also super interesting to see about 5 brides running around the streets. Apparently Labor Day Weekend is a very common date to get married? 

Chicago's Skyscrapers

I not only learned a lot about architecture, I had the privilege of visiting this city with my mom who studied both her bachelors and masters in architecture and sister, who graduates with a BA in architecture next May. They were giving me all the insights on famous architects like Frank Lloyd Wright (more on him soon), and Ludwig Mies Van der Rohe. Yeah, I got pretty lucky! 

The only part that I really wish to not speak about is The Ledge at Willis Tower (previously The Sears Tower). Let's just say I freaked out and couldn't take the picture. That place was built for maniacs! 

chicago mural chicago street art

The view from the Willis Tower -

The view from the Willis Tower - yikes!

Millenium Park

I absolutely loved this place. This is where Cloud Gate or "The Bean" and a magnificent outside theater is located. It is so beautiful, modern and the skyline view is to die for! Watch me have a little dorky fun in the pictures bellow:

Chicago's Navy Pier

To be completely honest with you guys, this was the most underwhelming part of Chicago for me. I mean it was beautiful, but I think it is more targeted to kids. The view though, makes it completely worth the Uber ride! Plus, you can take the Architectural River Tour from here, which is a MUST if you are visiting Chicago for the first time. 

Magnificent Mile (Michigan Ave)

Think of this street as the 5th Avenue of Chicago, but with higher sales taxes. Yeah, Chicago is more expensive than New York, so if you are planning on shopping for a new purse or outfit, I would recommend skipping on Chitown. Their sales taxes are above 10%! 

But besides the high costs of shopping, this avenue is beautiful and has lots of fun places to eat outside and enjoy the nice weather (when you can). 

Frank Lloyd Wright's Robbie House

If you grew up with architects like I did, you most definitely know about Frank Lloyd Wright. His attention to detail is out of this world and I really enjoyed the Robbie House Tour which is right in front of the University of Chicago. 

My only advice here is to arrive before 9am so you can get a tour guide! They go by really fast. 

Insider Tips:

If you enjoyed any of the things I did in Chicago (in a short 5 day trip), I would highly suggest purchasing a Chicago Explorer Pass. I got it on a great Groupon deal so watch out for that. This pass will help you plan and budget yourself beforehand and save a good amount of money on Chicago's basic attractions. It's perfect for a first time tourist like I was! *This post is not sponsored!

Last but not least, Chicago is a place for FOODIES and I ate like a happy mofo. So if you would like a separate post on all the places I ate at, let me know and I'll have it ready as soon as I can. :)