Why I moved to NYC from Chicago: My Midwest life felt stable but I was craving ‘energy and urgency’
- Stephanie sold her Lake Shore Drive condo and now rents a fifth-floor walk-up studio for $2,900
- ‘Ultimately, I decided to move because the comfort started to scare me. I wanted growth’
“The first time I carried groceries up five flights, I questioned my life choices,” Stephanie said.
Stephanie owned a one-bedroom condo in Chicago with an enviable Lake Shore Drive address. Her life felt stable and grown-up—but too predictable for someone her age. She decided to move to NYC to challenge herself and is thrilled with the Upper East Side, except for the five-floor climb to her place. Here’s her story as told to Kelly Kreth.
I was born and raised in the northwest suburbs of Chicago—classic Midwest suburb energy. Think: recreational sports leagues, snow days, and neighbors who knew your family.
As an adult, I owned a one-bedroom condo and lived alone—I was in my independent Midwest woman era.
I purchased my one-bedroom condo for $198,500 at the height of the pandemic in July 2020 with a 2.75 percent interest rate. It was such a good deal I never thought I would ever sell it, but that’s exactly what I did four years later for $224,900.
[Editor's note: Brick Underground's series The Newcomers features first-person accounts about why a renter or buyer decided to take a chance on NYC.]
The building had a doorman and elevator, which made it feel very polished and secure. The unit did not have a washer/dryer, but it did have built-in AC units that I controlled with a remote that made it almost feel like central air. There was plenty of space to host friends. It was roughly 850 square feet—about double the size of my current NYC apartment.
Groceries were usually Jewel or Trader Joe’s. I did a lot of meal prepping. I had a huge kitchen with lots of counter space. Ordering in meant Thai, sushi, or Rosati's pizza nights.
I loved hosting dinner parties, having long-standing friendships, and work happy hours—it was comfortable and familiar.
The area was safe, residential, and lined with trees. Very peaceful. The building was across the street from Lake Michigan and I liked saying my address was on Lake Shore Drive.
I had a car and alternated between driving and taking the Chicago Transit Authority. The commute was manageable and predictable.
I worked as a buyer for a well-known media agency, managing large-scale media budgets across linear, programmatic, and social channels. November marked 10 years with the company.
Why she decided to move
I loved the space and the building amenities. It felt stable and grown-up. What I disliked—or maybe outgrew—was the comfort. It started to feel too easy, too predictable. I started craving more energy and urgency—something that pushed me.
Ultimately, I decided to move because the comfort started to scare me. I wanted growth. I wanted challenge. I wanted to see what would happen if I chose the harder, more ambitious path and I decided to move to NYC.
I perused StreetEasy and ended up seeing about a dozen apartments remotely; it was a humbling experience to learn what you can get for your money in NYC.
I worked with a broker who, unexpectedly, became my very first friend in New York. My mother, a real estate agent in Tennessee, introduced me to Samantha Michel, an agent at Keller Williams NYC. Samantha helped me navigate the stress and challenges of my move. I am happy to call her a friend.
Wanted: Q train and natural light for less than $3,000
My priorities were safety, proximity to the Q train, natural light, and something within a budget of $3,000 per month.
Samantha saw places on her own and we had video calls from each one, so the first time I saw my apartment in person was on moving day. Chicago felt measured and calm, while things in NYC moves fast—paperwork, deposits, decisions—everything happens quickly.
When it came time to move, I only brought only a few pieces of my furniture. Downsizing allowed me to curate the rest intentionally.
Samantha met me on moving day to bring me the keys and saved me a trip Downtown. She knew that driving a U-Haul van into NYC and then double-parking on a Manhattan street was already going to be a lot. She stayed with me until the last box was brought upstairs.
What she likes about her new place
My place is a fifth-floor walk-up studio on the Upper East Side. It’s about half the size of my Chicago condo—a true New York shoebox in the best way. I pay $2,900 per month. There’s no doorman and no elevator. But it does have an in-unit washer/dryer.
Living in a walk-up has definitely strengthened my legs—and my resilience. The first time I carried groceries up five flights, I questioned my life choices. However, the first time I walked home past brownstones at dusk, I knew I made the right one.
I love my neighborhood. It is elegant, walkable, and polished. It’s old New York charm mixed with ambition, brownstones, Central Park mornings, Madison Avenue windows—it all feels cinematic. I love the feeling that something interesting could happen any day.
But I still dislike five flights of stairs after grocery shopping.
Luckily the local grocery and dining options make hiking up and down so many stairs worth it. Some local faves: Counter Service, JG Melon, Cafe Luca's, Caffe Buon Gusto, Terroir, Via Quadronno, Ralph’s Coffee, Eli’s Market, Trader Joe’s on 59th or Whole Foods on 87th depending on the scenery I want that day. I also love to spend time on the steps of The Metropolitan Museum of Art and go to Central Park.
I got to keep my job because I transferred to our satellite office in Hudson Square. I have no car here; I’m fully subway-based now. The Q train is my main line, and the commute feels fast and energetic.
My friends who have visited say it feels very “me”— ambitious and intentional. And making new friends has been easier than expected—New York women are incredibly impressive and supportive.
Dating has been interesting—let’s just say the five-floor walk-up is a great filter.
I’m giving myself two years to decide if I am staying, but I am definitely renewing my lease. Overall, this was a great decision; I traded square footage for momentum.
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