36 Hours in Chicago

Last week, I added a flight to Chicago before I headed back to Denver from my New Orleans & Dallas trip, which gave me 36 hours to explore a new city: Chicago!
Tip: use, or their app, and you can filter results to show from your airport to “everywhere,” and pick a cheap location! That’s how I chose Chicago, and paid less than $50 for my flight! 
I landed in Chicago Monday night and checked into Chicago’s Hostelling International off Congress Ave, and immediately crashed. (Ladies, this place is 100% safe, clean and I enjoyed meeting other female travelers!)

Check out the gif of my room, which had lockers (you bring your own lock), and lights in each bunk so you don’t disturb others. I plan to check out other Hostelling International locations, simply because I was so impressed with the Chicago location.

Because I had just one full day to explore the city, I tried to make the most of my time there.

A few things you should do if you plan to visit Chicago (by the way, everything here was free, except the Art Institue, which was only $15):

1. The Riverwalk: the Chicago River runs through the city and you can access some shops and restaurants right on the riverwalk. I ate at a nice little Italian place for lunch near the river, before attempting to catch a boat to Lake Michigan (plans fell through due to weather).

Screen Shot 2015-05-10 at 8.25.05 PM
Most amazing mussels for lunch!

There are also lots of neat buildings to snap pictures of, like these guys:

The Marina Towers – Also famous on the cover of Wilco’s, “Yankee Hotel Foxtrot.”

2. The Art Institute of Chicago: OK – I saw SO MANY famous paintings here! Van Gogh’s self portrait and the painting of his room are two that I just stared at for more than a few minutes. It was so surreal seeing tese famous paintings in person, and still able to feel what he was feeling and thinking when he painted them. It reminded me of “The Dead Poets Society,” when Robin William’s whispers, “Carrrpeeeee Dieeeem,” in that famous scene.

Vincent Van Gogh – Self Portrait
Of course, all I could think of when I saw this painting was, “Ferris Bueller’s Day Off.”
Georges-Pierre Seurat – A Sunday Afternoon on the Island of La Grande Jatte.
Vincent Van Gogh – “Bedroom in Arles.”

3. Willis (formerly Sears) Tower: You can ride all the way to the top of the Willis Tower to the SkyDeck and view the entire city…except when it’ foggy.


I was slightly bummed that there was zero visibility, but it was still really cool to be in a cloud.

Screen Shot 2015-05-10 at 7.57.26 PM

It was also incredibly amazing when the clouds lowered for about five minutes and we were above the fog!

 4. Cloud Gate, aka, “The Bean:” I don’t know why, but I was most excited about seeing Cloud Gate – a public art installation by British artist, Anish Kapoor. It is also GREAT for selfies!

IMG_0758 IMG_0776 IMG_0790 IMG_0791
5. Walk around the theatre district at night! This was fun for me – for some reason I just love the way theatre signs look when they are lit up! I even stopped to take a long exposure picture of the famous, Chicago Theatre:
IMG_0851 IMG_0857
So that’s basically how I spent my quick trip to Chicago! What did I miss? I definitely want to return and see more of this awesome city!

Share on
Previous Post Next Post

You may also like

No Comments

Leave a Reply