Chicago Travel Diary

Chicago recently stole my heart.

I was there for a quick trip to celebrate my brother graduating from Naval boot camp. He graduated! (and a side note: we were all so emotional and proud of him). We were all so excited to see him, and so proud of such a huge accomplishment. Even though we were only able to see him for a day (he left for school and more training early Saturday morning) it was still so lovely to be able to share our first deep dish pizza experience together & lemme tell you it was DELISH.

My fiancé and I flew in on Wednesday morning. We stayed in Downtown Chicago at the Virgin Hotel. The hotel was really hip, and trendy and had such an awesome vibe to it. Everyone working there was so sweet and charming and just all around lovely. Our room was separated into two chambers: a dressing area and a bedroom. I was pretty obsessed with the set up; it provided enough privacy if needed, but was also still an open concept. All the amenities were pretty luxurious and trendy as well. We had a large bench seat, tiled shower that had a waterfall shower head. The bathroom had its own private entrance that didn’t make it feel claustrophobic. There was a sink area, as well as a perfectly lit vanity station – that was a literal DREAM you guys. The dressing chamber also had two closet areas that were a great size for hanging huge jackets, and storing all of our necessities. Us Californians… we were not used to the Chicago cold so that space was very needed.

The bedroom chamber was small, but in the most perfect way. It mainly housed the bed (we opted for the king size bed) and that was all you needed because lord the bed was THE most comfortable bed I have ever slept in. There was also a mini fridge and daily supplied snacks, a desk/table area for working, really convenient shelving, a lovely flat screen tv that pulls away from the wall and a pour over coffee and tea set up. I loved the setup of the rooms. They really used all the space in a smart way, and I loved that. There is daily room service, an almost rooftop gym (25th floor), a cute diner, a nice lounge that is fully stocked (try the lavender mule – SO delicious!!!!) and a coffee and wine bar. They have a rooftop experience but it was closed since it is the winter time. I am sort of bummed that it wasn’t open because we were located pretty close to the river and the downtown skyline, even if you’re part of it, was amazing. Overall, I loved the experience at the Virgin Hotel and will absolutely go back. Looks like they are opening one in San Francisco so I will definitely be visiting them there!

Wednesday evening we met up with my mom, dad, grandpa and brothers girlfriend for dinner and drinks at the Commons Club. The food was great and the drinks were amazing. On Thursday we ordered breakfast in bed (because what else do you do on a mini-vacation?). We did some pretty basic touristy things on Thursday as well. We went to Millineum Park, saw The Bean, walked around and explored and also stopped at the Art Institute of Chicago.

I love museums so I had to make sure I pulled a stop in at least one. I got so lucky and I was able to see some of the greats like Pablo Picasso, Andy Warhol, Vincent van Gogh and other amazing artists. They had a huge Impressionism exhibit and their modern and contemporary art exhibits were really cool. Whats funny is that, I truly had to use the restroom so badly that I sort of stumbled upon the art institute. I knew it was there, but it just so happened to land so perfectly in my lap. Plus, stepping out of the cold for a few hours is always a good thing.

Later that evening, after warming up, we made our way to a really cool, some-what speakeasy sort of bar called Three Dots and a Dash. It is underground, and located in a back alley – so that’s what makes it speakeasy-ish to me. It was tiki themed and super tropical inside. It was a really great place. We got lucky and landed ourselves in a corner spot. We got really fun drinks and something to snack on.

Friday was reserved for our little sailor. We watched the graduation, met up with family and ate deep dish pizza. It was so amazing and lived up to its hype! After we spent the afternoon with my brother, getting as much time with him as possible. We played cards, laughed and caught everyone up on the latest deets – it truly felt like he hadn’t been gone for the last few months. We took him back to the base in the evening, as he had to fly out early the next morning. It was rough, but knowing that he was finally able to have his phone and we are now able to talk to him whenever we want, it felt much easier to say goodbye this time.

Saturday we had a pretty good amount of time to kill before our flight, and Mauricio and I ended up taking a two hour Big Bus tour around the city learning about the city architecture, history and seeing the best places the city has to offer. It was the most perfect little two hours, seeing all that we could in the last moments in the windy city.

Chicago was a really wonderful experience. We absolutely want to come back to explore even more (museums, sorry babe!) and we can’t wait.

Chicago, you absolutely stole my heart, despite the cold. See you soon



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