Chicago & Stitchfix

I think I have been in my own bed a total of maybe twenty times in the past two months. I have seen more suitcases than my own closet and have been inside of more airplanes than my own car. Over the past year or so, I have come to have a really deep love for traveling and exploring new places- I appreciate the art of picking up and just going. Between one new country, two new states and back and forth within California, I have traveled every weekend since the second week of may and now each trip and the people involved have a certain special place in my heart and memories. 

Since it’s still fresh in my mind, I’ll talk about my most recent adventure to Chicago.  

I have a friend group, we affectionately refer to ourselves as “The Cheetah girls”, this year was a big year for the cheetah girls, we had two birthdays and a graduation this month alone with other transitional moments within our friendship as well. So how do we celebrate all of this at once? A trip to Chicago!

Initially only two of the girls had booked their tickets and said, “Hey, we’re going to Chicago. Ya’ll want to come?” and then shortly after, two of us booked our tickets and chipped into an airbnb. It was our first “girls trip” together and we were pretty PUMPED about it. 

Packing for trips is always quite a tedious task for me because I tend to want to plan my outfits based off what I know we’re going to be doing/ what spaces we’re going to and looking at their aesthetics. Basically, my mind is always in content creation mode and vacation and traveling are great ways to do that.

For this specific trip, I had some help from Stitch fix! I told my stylist details of my trip and updated my Pinterest board with styles and outfit inspirations for her to understand more of my fashion taste. My stitchfix came, I styled my outfits and then packed up and the four of us headed to Chicago!


When we first arrived, we had the sweetest Lyft driver (Shout out to Terry) and were immediately dropped off in the middle of downtown and had a taste of Chicago breakfast at a highly recommended spot. We had flown overnight, landed in the weird hours between morning and afternoon and needed pancakes and coffee ASAP. We had sometime to kill before checking into our airbnb so after breakfast, we strolled around our neighboring area for a bit to check out the coffee spots and cute little boutiques. Considering our lack of sleep from the night before, once we were given the go ahead we checked into our home for the next few days and took the best nap of our lives, then once rising from our slumber, got ready for deep dish pizza round one. While we waited for food, I stumbled into the most adorable bar/ bookstore and fell in love with every single aesthetic. 

During dinner we sat and devoured garlic bread to curve our sassy hanger and then the deep dish cheesy goodness. We chatted about our plans for the next few days and then leaving our carb regrets in the booth, we headed on the much needed stroll back to the airbnb.


Day two might have been my favorite day. 

I was in charge of finding most of our food spots, since YELP is my speciality and so is finding where the aesthetics are, so we ventured to another highly recommended brunch spot not far from our airbnb. Our morning started full of belly laughs due to our sassy Chicagoan driver who was not at all impressed with our touristy plans for the day and then we arrived at the Little Goat. The food was amazing and the vintage aesthetic made the old soul in me drool!

After we were caffeinated and full, we started our trek towards tourist spot #1- the Sky deck. We went so high up that our ears actually popped when going in the elevator. There was something about standing over a ledge that looks 1,353 feet down that was both terrifying and exhilarating at the same time. It was a 60 degree view stretching up to 50 miles and it was absolutely incredible. Being able to see that much of a city you've never been to before was breathtaking and because there was about 60 more people behind you to see the same view, the moment went fast. 

And then came the conservatory, one of the girls on our trip who graduated and had a birthday absolutely loves plants. She has quite a few of her own, names them all and listens to a weekly live video on how to take care of them all, we have gotten into the habit of buying her cactus shirts and "plant lady" mugs, so when I stumbled across this gem I knew it had to be part of our day.

The Garfield park conservatory was every green magical dream you could think of. I specifically styled my outfit because of how it would look in the conservatory, a grey and white striped maxi from Stitchfix paired with a hat and statement earrings with a good ol pair of strap sandals for color pairing and comfort. 


We finished the day off with leftover deep-dish pizza round two and wine and then strolled down the street from our airbnb to grab some dessert from Jennis Ice cream. 

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Day three I knew we would be walking around quite a bit, so I did a comfy bottom half outfit pairing with a pair of mom jeans and tennis shoes and my Stitchfix floral tank blouse and pink tassel dangly earrings.

We adventured to the famous Chicago bean whose original name is actually "Cloud Gate", took an architectural tour and learned about the context and history of all the amazing buildings in Chicago and ended our touristy spots with a visit to the beautiful Navy Pier. We ended our last full day shopping around and visiting the cutest tiki room bar that one of the girls found with all the aesthetics (my favorite if you couldn't tell).

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I came to absolutely adore Chicago with its city meets southern hospitality type of vibes and the way that I ended up learning so much from our Lyft drivers, tourist escapades or random strangers. Our first girls trip was an absolute success and though I have loved packing and leaving for the past two months, I am excited to be home for a bit before taking off again.



 now it's your turn.

StitchFix is doing a giveaway for the month of June where all you have to do is schedule your own fix and automatically be registered to win a getaway trip of your own!

Tell your girls your flight is booked and have them join in on the fun or just take a much needed solo trip-- either way, this is the most beautiful time to pack and bag and go.

Go find stories in an unfamiliar place and leave pieces of your hearts in the corner of coffee shops.

Where will you go? what memories will you make?

Check out the giveaway here


Arielle Estoria