The hardest part about planning a trip, is trying to decide which attractions and activities you will fit in while you’re there. Since I only had two days to fit everything in, I really had to prioritize!
Since my boyfriend lives close to the windy city, we decided to make the 3 hour drive into Chicago. Since he drives a huge truck, we also decided to rent a car that was more gas efficient. I think the highlight of this trip was seeing him drive this miniature car down the highway.
I think driving in really gave me the feel for the city, as I got to see the Chicago skyline & the water as we drove in. The first thing you will notice is how tall every building is. It’s like you’re surrounded by skyscrapers, and each building has a different look to it. We spent about 10 minutes trying to point out the Willis Tower and John Hancock building.
We decided to stay at the W hotel for the night, and it was a perfect choice. Not only was the hotel stunning (as most W’s are), it was right by Lake Michigan. We got a room with a city view, and luckily for us we scored a room on the 30th floor. We were in the perfect location to walk to many places, as well as uber if we needed to.
The first thing I wanted to do once we got there was visit the Willis Tower. That was on the top of my list, so I had to make sure we got it done! We ubered there from the hotel & upon arrival the first thing we observed was the amount of people there. I thought on a Friday we would have more luck with less crowds, but boy was I wrong. Now, you can opt for a “fast pass” to skip the line, however we decided to wait it out. The wait wasn’t too long (about 45 mins) before we got to the top.
The elevator ride was a bit shaky, which had a few of us (my bf in particular) a little concerned! However, once you get up to the 103rd floor, it is breathtaking.
Of course, if you make it up there, you absolutely have to visit the skydeck!! It is a bit scary at first, walking out onto the glass floor, seeing straight below you, your mind sort of plays tricks on you. I carefully stepped my way onto the deck, took a picture, and ran out! If you can muster up the courage, I definitely recommend it to everyone!!
Now on to the most important agenda for a trip: FOOD! I told myself I absolutely had to try a Chicago-style hot dog! We ended up at Portillo’s which is sort of like a huge hot dog stand that also serves burgers, ribs, chicken, and almost anything you could want. You wait in line to order, then pick up your food once they call it out of the pick-up window.
My Chicago-Style Hot dog was worth the 3 hour drive! It was delicious!!
After our meal, we both decided it would be best to walk off our “itis.” We decided to walk to Millennium Park so I could have a look at the bean. Of course, along our way we got to do some amazing sightseeing!
The bean is definitely a Chicago staple, and I think everyone should see it at least once. Once you get there and see it, your first inital reaction might be: “That’s it?!” There are always a million people there, so you sort of have to get in where you fit in for a photograph. The coolest part about the “Chicago Bean” is the reflective stainless steel material that allows you to look into & see the Chicago skyline looking back at you. It is really neat.
Now time for dinner!! I was told by many people that I just had to try out Pequod’s deep dish pizza. I am sure glad I listened!!
Pequod’s was sort of like a hole-in-the-wall restaurant. It had brick walls, and tables all pushed together, and it felt like you were deep in the heart of Chicago. It wasn’t touristy at all, which we both loved. We got a small deep-dish pizza and shared it. The slices are huge, and although I didn’t finish both of my pieces, my boyfriend did and he basically went into a food coma. The pizza was the best I have EVER had! The sauce, the meat, the cheese..everything! Although I do think my favorite part about it all was definitely the caramelized crust on the bottom. I could eat that again! After that meal, we had to tap out. We were full and tired!
Since we had hit almost everything we wanted on the first day, day 2 was sure to be a breeze. We decided to walk to brunch so we could get a little more of sightseeing in before we left. We walked through the park again, and even stumbled upon a Nutella restaurant!! If the wait wasn’t so long, I would have loved to check it out!
After brunch, we took an uber over to the United Center so we could catch a glimpse of the Michael Jordan statue. It’s now located inside of the Center.
After we visited the statue, we made our last stop on the Navy Pier. I will admit, this was not very exciting. There is a ton of people walking around, and honestly not much to do at all. At least I can say that I’ve been, right? I don’t recommend adding this to your list if you are pressed for time. It’s just not worth it. It does, however, give you a great view of the skyline as a backdrop to your picture!
The only thing we didn’t get a chance to make it to was the John Hancock tower. I would have loved to see the signature room, but there is always next time! Now I have a reason to go back!