Feels like NY, Summatime Chi, ahhhhh
For the past year, something in Chicago had been calling my name. I’d been meaning to take a trip to visit for monthssss. One day I checked flights… Then I checked my bank account and thought, birthday trip?
I took the trip this summer a few days before my 26th birthday. I chose not to say anything to anyone until it was all set in stone. It was nerve wracking but I had officially booked my FIRST solo trip!
Call it soul searching, call it a mid-twenties crisis (cue twenty somethings by SZA). I just knew this first half of the year had been a lot and I needed some time alone.
Traveling Solo
Why choose to travel alone when I would have easily been accompanied by my friends or my family?
This trip was one that I needed to push myself out of my comfort zone.
In my day to day life, I am fortunate to be surrounded by so many people that I love and care for. I think that often times, especially as a woman, first generation, a daughter, a sister and a friend, it becomes so easy to forget to pour into our own cups.
So yes, I could have taken this trip with my loved ones. But this trip wasn’t about that or them, it was about me.
I came to recharge and recenter myself, to press pause, to think and release… to figure out what *I* wanted to do as I stepped into this next year of life. (26 sounds real serious like, what?!)
and the trip was exactly what I needed.
Where I stayed:
Chicago has tons of neighborhoods to choose from depending on the type of stay you would like. As a true city girl, I wanted to be in the mix! So when deciding where I wanted to stay I focused on location location location.
I wanted to stay on the Riverwalk for the views but the budget just did not allow for that. Especially on my own.
So! I decided to stay in the River North Area right off of Magnificent Mile:
I loved it! This area was walking distance from the majority of things I wanted to do during my trip. Tons of restaurants and shopping near as well. Anything that was slightly out of the way, I ubered and it was always under $10!
Coming from Miami being used to needing a car for everything, being able to walk to most things in Chicago was a refreshing change of pace.
I popped my airpods in, walked around the city and literally was in my own RomCom. (I probably played Love Train by the O’Jays a good 50 times) It was lovely.
Shout out walkable cities!
The public transportation system was also top tier.
I took the blue line train from the Chicago O’Hare Airport straight into the city for $5 vs. what would’ve been a $60 uber.
Hotel vs. Airbnb:
Listen… I love myself a bnb but for certain destinations, the hotels have it!
Because I was traveling alone, I felt more secure in a hotel.
I stayed at the 21c Museum Hotel Chicago:
This hotel was curated as an art museum in the lobby and hallway areas. It showcases a wide range of artwork all throughout the hotel which I thought found unique! It added to the experience and captured some of the vibrancy in the city.
I landed pretty early in the morning and they were accommodating with an early check in! +10 pts for them.
what to do, what to doooo
I was in Chicago for four days. Having done tons of research on what to do, there were so many options to choose from!
I did not want to overwhelm myself with a rigid itinerary. Here’s a look at how I spent my days in the windy city:
Day 1:
- Land into ORD airport at 9:00am
- Check into the hotel & freshen up.
- First things first… Mr.Beef. This was a quick 10 minute walk from the hotel and I loved the bear! So wanted to make sure I stopped by here first.
- Carmy, ily. You need to seek therapy but my feelings remain the same.
- WNDR Museum
- This museum was so fun! It was a highly interactive futuristic art museum. I spent about two hours here walking around the different exhibits that they had.
- This night they also hosted a night market, there were tons of cool local vendors, a DJ and drinks. I bought the cutest strawberry earrings there that I love.
- Stopped by the Riverwalk
- To say that this city is gorgeous is an understatement.
- It was such a nice place to walk around, find a spot to sit and relax to have a drink.
- Uno’s Deep Dish!
- I love pizza and a saucy one at that – I had my first deep dish and fell in loveee.
- Called it an early self care night. An eye mask and sauvigon blanc really hates to see me coming.
Day 2:
- No one told me it would be 60 degrees in June?? I was unwell.
- Breakfast at Goddess and the Baker
- Fire… I love a cute coffee shop that also gets the food right! This was walking distance from my hotel which came in handy.
- The Bean
- I was so happy to have gone after they opened it back up. It was a tourist activity and a bit too crowded for my liking. But, one you have to do at least once if you visit.
- This area is centrally located to so much. It was such a nice day out that I chose to just take a stroll around the city.
- Everyday People
- I’ve gone to EP’s in Miami and NYC many times but Chi was different!
- Going to this party alone was uncomfortable, but once I arrived, it wasn’t as intimidating as I thought. I met cool people, had conversations, and enjoyed a couple of free drinks. 10/10
Day 3:
- Walk through the Magnificent Mile to the Riverwalk and then to the Art Institute of Chicago.
- The Art Institute of Chicago
- I spent most of my day here… The museum had a wide range of exhibitions that allowed me to explore for hours.
- There is a café area in the museum. I enjoyed my lunch there and was able to reflect on my trip as I journaled.
- Architecture Tour: Sunset
- This was by far my favorite experience on the trip.
- The Architecture of Chicago is incredibly unique in comparison to other major cities.
- This tour took us out into Lake Michigan where we viewed the cities beautiful skyline in its entirety. I even got a visit by a special someone. LLM.
- Birthday dinner!
- LH Rooftop
- This bar was located in the London House hotel and was in the prime location for city views. Overall, based on the reviews I thought it would’ve been nicer. I felt the views were great but the rooftop itself was crowded and just a regular bar.
- Olio E Piu
- The best meal I had on my entire trip.
- This Italian restaurant is located right on River North. It was intimate, serene and exactly what I wanted to experience on my last night in Chicago. The service was phenomenal and the food was amazing.
- LH Rooftop
Day 4:
On my fourth and final day in Chicago, I had about half a day to kill before my flight.
I wanted to take a moment to wind down, ease into the travel day ahead of me. I chose to go to a coffee shop to read and draw.
- Breakfast at Goddess and the Baker
- Yes, I went back twice. When I like things, I like them. 😭 Sue me.
This day for me was so special. I reflected about my time in Chicago and truly connected with myself. I spent probably about 5 hours mindlessly drawing, reading and enjoying my own company.
Moments like those were what I wanted from this trip. In that moment, time seemed to slow down and stop for a second.
I wanted that stillness, I was craving it. I wanted to reconnect with myself in ways I hadn’t had to face before. Literally, completely alone.
I was in a city where I knew NO ONE. How crazy was that?
I kept thinking of how I’d manage to look back at this moment once I’m older. How grateful I am to be fortunate enough to give myself this experience.
If you’ve made it this far (👀) I hope you take that leap. I hope you take some time to yourself, explore somewhere new and immerse yourself wherever you go. This life is too short not to!
xo,
Nani
Go with Nani 