Chicago Diaries: Adventures & Outfits in the Windy City

This summer, my family decided to take a trip to Chicago, Illinois! Having seen all these movies that take place there (ex: “While You Were Sleeping,” “Ferris Bueller’s Day Off”), I was super pumped about going there. Many people I knew have also gone there before and have only said good things. Well, I personally agree with them because after spending time there, I can say that I really enjoyed my time there! So without further ado, here is a fast-forwarded recap of our days in the city full of skyscrapers!

Day 1

Saturday was our first full day (Friday was just the arrival day, and all we did was walk around the hotel eat a deep dish at Giordano’s) and basically a museum day. I don’t know about other people, but my family and I have always loved checking out different museums from all over. I don’t know – are they boring to you? Anyway, we visited the Adler Planetarium and Shedd Aquarium, and while I liked both, I definitely preferred the aquarium. It was probably one of the best ones I’d been to with a huge collection of fish, coral, etc. While these places were kid-friendly, they were also informative/interesting for adults to enjoy.

Chicago Skyline

After exploring both museums, we spent time walking around Lake Michigan, which, by the way, is so incredibly scenic from the museum district. Seriously – if you want photos by the lake with skyline in the background, this is your place to go to! So, I’d say that the first day was very well spent!

Gingham and Jeans
Outfit: Top | Jeans | Sneakers | Sunglasses

Day 2: 

We started off the day by checking out yet another museum – this time, the Field Museum. It was a very spacious natural science and history museum with a lot of wings and exhibits. Around mid-afternoon, we headed to the Magnificent Mile (also known as Michigan Avenue) for lunch and some light shopping. The line of shops was so incredibly long and pretty much impossible to thoroughly explore in just 2-3 hours, so we only stuck to a part of it. I’d still recommend walking through it regardless!

Afterwards, we headed to Millennium Park where there’s the famous Cloud Gate, aka “The Bean.” It was just as large and shiny as I had expected it to be. It was also one of the most crowded sites in the city, so just getting a decent snap of it was a bit difficult.

Chicago Bean

We had a nice, relaxing time walking around that general area as the sun set and the winds blew.

Gingham and Mules at Millenium Park
Outfit: Top | Pants | Mules | Sunglasses

Day 3:

This day was probably the most jam-packed. We went on a boat tour (which I admit to falling asleep on) before heading to 360 Tilt. If you don’t know what it is, it’s basically an attraction where you go up the John Hancock building and get tilted outward, inside a window, over 1000 feet – talk about thrilling!

Later on, we took some photos at the Chicago Riverwalk where I personally think you get the best shots of the Chicago River and skyscrapers up close.

Romper and Straw Hat
Outfit: Romper | Hat

Afterwards, we spent some time at the Navy Pier. By this point, the temperature outside was actually getting quite hot, but of course, still decent compared to Texas heat. We ended the day by doing a little more shopping on State Street before eating dinner and heading back to the hotel.

Navy Pier

Day 4:

We started of the fourth day by climbing up the Willis Tower to check out the Sky Deck. I thought I would have been more scared about standing/sitting on a see-through window on top of a skyscraper, but nope – it wasn’t bad at all!

Chicago Skydeck
Outfit: Top | Bottom Sunglasses | Shoes

After grabbing some lunch, we spent some more time on State Street and checked out some stores here and there. We also went to North Avenue Beach later on, and for the first time in ages, I actually went in the water. So quick story time –

Sand on the Beach

When I was much younger, my family and some family friends of mine all went to Galveston Beach, and if you’ve ever gone there, you know that it’s pretty disgusting and just a stretch a murky, brown water. Well, there I was playing around in the water, all happy, when suddenly, a freaking jellyfish stung me (or at least I’m pretty sure it was a jellyfish because it hurt really badly). So yeah – ever since that day, I’ve remained anxious about swimming in open waters such as lakes and oceans.

Black Bikini and Straw Hat
Outfit: Top | BottomHat | Sunglasses

Day 5: 

This was our final day but not a full one since we had to head to the airport around late afternoon. We started off the day by checking out of our hotel room after everything was ready and packed. Then, we got some lunch at The Allis. To be honest, I had seen it all over Instagram and really wanted to check out if it was worth the hype. Luckily, it really was. Not only was the inside lovely, but the food was also just as tasty as it was pretty.

The Allis at Soho House

After brunch, we chose the Cultural Center as our final destination. It wasn’t my personal favorite thing that I’ve seen but it’s free and fun to explore.

And that was about it. Before we knew it, we had to head over to O’Hare and check in for our flight. If I had any advice to anyone wanting to visit the city, I’d say to stick to safer, tourist-filled areas since it is pretty crime-ridden outside of the nicer parts. Anyway, during my time in Chicago, I can confidently say that I had a blast!












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