Hello lovelies!

Chicago is every foodie’s and instagrammer’s ideal paradise, but as a solo traveller on her own (kinda) for the first time, it was an exciting adventure.


Despite what you may or may not have heard about Chicago (deep dish pizza, The Bean, etc!), I definitely think it is a trip worth taking! In early March last year I took it upon myself to fly out to Chicago, Illinois to check out what all the fuss is about, and I was not disappointed.

Chicago is actually a little more special than any of my past trips because it was the first solo trip. Well, it was half-solo. I stayed with a friend in River North that I had met on my Greece tour with EF Ultimate Break. One of my cousins lived in the city in Boystown at the time, as well.

Regardless of staying in a safe location with people I know, traveling anywhere as a woman in her twenties by herself is scary. Days before the trip, I experienced a wave of nervousness wondering if I could even do it. This was a test to see how independent I can be, and how I could use my wits to the best of my ability, and I did not disappoint myself (how awkward would that be if I did?).

I arrived in Chicago around 11 pm and I owe that entirely to poor planning. I will create a post that explains why, so stay tuned. With my travel backpack, I hopped on the train to get into the city and walked to my friend’s apartment. After our reunion from my 2014 trip to Greece when we last law each other, I went to sleep feeling nervous and excited for my trip.

• D A Y  O N E •

Day 1 officially and I was ready to independently venture this city. But first I met with my cousin for breakfast at Yolk. I hadn’t seen her in years so it was nice to be able to bond with her. We then went to Millennium Park where the famous Bean, or Cloud Gate, sits. Of course we had to get some pictures in.

To get a better view of the park, we went to the top of the Chicago Athletic Association. That’s when it started snowing. As a Vegas girl since I was a few months old, snow is something I’m not too familiar with. While I was rightfully freaking out, my cousin remained cool but whatever. It was SNOW!

After walking around the city, my cousin and I ventured back to River North where we enjoyed happy hour at The Hampton Social. Honestly, the entire vibe of this place deserves its own blog post. I will spare the details until then 😉 I had actually planned to go to THS on my trip, but I had ZERO idea it was right across the street from my friend’s apartment!



Did you even go to Chicago if you didn’t go to a sporting event? And no, I’m not talking about Da Bears. My cousin and I went to United Stadium to watch the Chicago Bulls against the Golden State Warriors. As much as I love Steph Curry, I had to root for the Bulls, and they won!


• D A Y S  T W O and T H R E E •

Day ⅔ were spent mostly solo, which I was still kind of nervous about. I ventured to several museums throughout the next two days. I have a thing for museums, even though you pretty much see the same thing in each one (with the exception of art museums). Regardless, it was still pretty incredible.






I went to Lou Malnati’s Pizzeria for lunch, and I gotta say… Deep dish pizza is out of this world. I think my favorite part of it was the crust, which I usually just toss. I loved the crispy-ness of it, as long as it’s in deep dish pizza form, of course!


The rest of the trip was mostly spent solo, but I did enjoy going out with my friend and my cousin. Below are some photos from my trip for you to enjoy!








I hope you enjoyed Chicago through my eyes! It was certainly an exciting experience being alone and soaking in all that is Chi-town. As nerve-wracking as it was, it was so much fun learning about the city and myself.

Stay tuned for other posts about Chicago if you’d like to learn more! Don’t forget to subscribe so you don’t miss a thing!

As always, thank you for reading! Leaving any comments or questions down below.

Until next time,

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Posted by:Diana Haddad

A 20-something travel, fashion and food blogger

3 replies on “A Weekend in Chicago

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