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72 Hours In Chicago: A Travel Guide

Do you ever have those trips that fly by so fast that it feels like they never really happened? That's basically how I felt about my trip to Chicago last week - it was so much fun, but flew by in the blink of an eye and now that I'm back home, preparing for the upcoming school year, it's hard to fathom that last week's trip to Chicago ever really happened.

One week ago tonight, I flew up to Chicago with my dad and sister for a three-day mini vacation. Although we were only there for 72 hours, it was the perfect amount of time to do and see everything we wanted to experience. Chicago is full of so many cool spots, so today I'm sharing everything we did on our trip (as well as a bunch of pictures!!).


We landed in Chicago around midnight, so we woke up kind of late Wednesday morning. We stayed at the Hyatt O'Hare since it was in close proximity to the airport, and after a simple breakfast at our hotel, we took the train into the city. Since Chicago is such a big, crowded city, it can be hard to find parking, and the parking fees are quite ridiculous (it can cost up to $100 for overnight parking!), my dad elected to not rent a car for our trip. I was a little skeptical on how we would get from place to place, but everything ended up working out well. We did a lot of walking and Ubering, but I really like walking from place to place as it gave me a chance to really see the city.

Upon arriving in the city, we checked into our hotel, and made our first stop at Facebook. My dad's friend works at Facebook in Chicago, and he invited us to come have lunch there and experience a virtual reality simulation. The Facebook office was really modern compared to a traditional office, and it was really cool! I loved getting to do the virtual reality simulator - it was so weird but such a unique experience.

After our stop at Facebook, we walked along the river for a little bit and decided to head to the Magnificent Mile - a mile-long street full of shops like Nike, Nordstrom, Zara, and Burberry. Since the shops were pretty high-end, we didn't buy anything, but I always love to go shopping even if I don't make any purchases! :) 

We also enjoyed some ice cream at the Ghiradelli Cafe, and it was amazing. My sister and I split a cookie ice cream sundae (she thought she could eat the whole thing by herself but I convinced her otherwise) and my dad had a strawberry milkshake since he doesn't like chocolate. We all really enjoyed our dessert, especially since it was hot outside!

After shopping, we headed back to our hotel to prepare for the soccer game we were attending that night. The whole reason we came to Chicago is because we wanted to see the Real Madrid vs. MLS Allstars soccer game at Soldier Field. Real Madrid is my favorite soccer team ever, and I absolutely loved getting to see them play in person. They ended up winning, which I was so happy about! It poured for the majority of the game, so everyone was soaking wet and freezing, but it was so cool to sit there and cheer on the soccer players that I couldn't have cared less about the weather! 

We finished off the night by enjoying a midnight pizza dinner at Giordono's. You can't go to Chicago without trying some of their famous deep dish pizza, after all! The three of us split a pizza stuffed with spinach, chicken, mushrooms and plenty of cheese, and it's probably the best pizza I've ever tasted! It was so filling, however, that we took home tons of leftovers.


On Thursday morning, we once again enjoyed a breakfast at our hotel, and then we were off to visit Navy Pier! We arrived around 10 AM, expecting it to be pretty crowded, but it was actually pretty empty which was so nice. We rode the ferris wheel, and we didn't have to wait in line at all! They also have lots of other rides and attractions, such as rock climbing, but we elected not to do those.

After Navy Pier, we walked around Millennium Park for a little bit. I'd wanted to see the Bean (aka Cloudgate) for a couple years, and it was so cool getting to see it in person. There's another park, Mary Bartelme, right next to Millennium Park, and it has a lot of kid-friendly things such as intricate playgrounds and rock climbing walls. We walked around that for a bit, too, and it was a lot of fun!

By this point, it was around lunchtime, so we headed to this place I had heard of called Luke's Lobster. My sister is a vegetarian, so she just had some leftover pizza at the hotel room, but my dad and I lovvvveeee seafood so we really enjoyed this place. He had a bowl of lobster chowder, and I enjoyed my first ever lobster roll. Even though it might seem weird to eat lobster in a state that's not on the coast, I promise you, it is so good.

Later on in the day, we headed to Armitage Avenue to do a little shopping. They have the cutest boutiques and bakeries there, and I also stopped this colorful wall to take a picture.

For dinner, we had the best meal of our trip at Cafe Babareeba. My dad went to Spain earlier this year, and he raved about their tapas and paellas, so when I found this place while researching, I knew we had to come here. I forgot to make reservations, so we did have to wait an hour, but it was well worth the wait as my dad and I both agreed that this was even better than deep dish pizza. We shared an appetizer of potatoes with tomato aioli, and split an enormous paella con pollo y verduras para cena. (#spanishskills)

While shopping earlier, my sister pointed out an ice cream place called Jeni's Ice Cream that looked good, so we went there for dessert. It was even better than the ice cream at the Ghiradelli Cafe the day before. Their ice cream was all natural and made with high quality ingredients, which is why I think it was so good. You really can't beat all natural foods! It reminded me of the ice cream I had in Waco a couple weeks ago, and I savored every bite. I had the salted peanut butter, and the sweet and salty combination made it the best ice cream I'd ever had.

// FRIDAY //

We headed to the Sears Tower early Friday morning to go visit Skydeck, a glass ledge on the 103rd floor of the building. You can walk out there and see up to 50 miles away! A friend of mine told me to be there at 9AM when it opens so you don't have to wait in line, and that was definitely good advice!

After Skydeck, we walked around the city some more, and I visited this mural that I had wanted to see. It's hard to tell from this picture, but it's a giant flamingo!

Our hotel was right by the Magnificent Mile, where we had gone earlier on during the trip, so we stopped at the Dylan's Candy Bar there to get some candy! I had never been to Dylan's before, and it was nothing short of magical. The place was filled with bright colors, sweet treats, and smelled of chocolate and sugar. I picked out some candy bars to take back home to my mom and other sister as a small souvenir, and my sister and I got one too! I picked out cookie dough, she picked out red velvet, and we brought a hazelnut one and a cupcake one back home. They also had interesting flavors of chocolate bars like potato chip, bacon, pizza, and popcorn, but those were a little too interesting for us.

My sister had really wanted to go kayaking on the river, so we rented a couple kayaks for an hour and paddled around the river. I wasn't expecting to like it, but I ended up really loving it and it was so fun! I don't have a picture of it, but it was one of the coolest things we did on our trip.

We also stopped at this cupcake place called Molly's Cupcakes that I had read about. It was featured on Cupcake Wars, and famous for their filled cupcakes. I had a cookie dough one, my sister had a cake batter one, and my dad had a peach cobbler one. I didn't care for the icing, but the cake was so moist and rich that it honestly didn't need icing (words that I never thought I'd say, being the icing lover that I am)

On our way to the airport, we walked around Lincoln Park since it looked pretty while driving by it. It was by far the prettiest park that we visited - there was a gorgeous lake surrounded by the prettiest flowers. Needless to say, we had a pretty fun photoshoot there... the picture of my sister and I fighting is completely staged but the one where she's kicking my dad in the face is 100% real and I captured his reaction perfectly :)

The last thing we did before heading to the airport was go to Chicago Pizza and Oven Grinder to try their famous pizza pot pies! It's a little cash-only hole in the wall place, but it had a line out the door and a two hour wait. Apparently, it's the go-to pizza place in Chicago. We opted to get our pizza pot pies to go, so we wouldn't miss our flight, and we ate them at the airport once we got there. I really liked the crust on the pizza; it's dense, chewy texture attested to the fact that it was homemade. I preferred Giordano's to this place, but it was still delicious!

A couple things about Chicago I noticed:

- The weather is really weird. It will rain one minute and be sunny the next. It was like this our whole trip.

- Drivers honk. All. The. Time.

- Every store is built up. Since there's not a lot of room for stores to build out, they simply add multiple floors. We visited a 7 story Target and a 4 story Walgreens.

- Chicago has the best parks. Dallas has a cool park, Klyde Warren Park, but Chicago's parks make Klyde Warren seem like nothing.

- We accidentally visited Chicago on the same dates that Lollapalooza was happening. There were crowds of Lollapaloozers (that's what my sister calls them) everywhere... and let's just say they needed to put down the red solo cups and put on some more clothes.

Overall, it was an incredibly fun few days and I would love to head back to Chicago sometime! If you ever get the chance to go there, you definitely should. I never really considered Chicago to be a good vacation destination, but now that I've been there I couldn't recommend it more!

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