Relocation from NYC to Chicago: Ashley’s Perspective

I’m Dorothy Moody, owner of HotSpot Rentals since 2012 and a former New Yorker. I’ve been in the apartment rentals business for ten years and have helped thousands of people move to the Chicago area, so I know from experience that moving is one of the most simultaneously exciting and nerve-wracking experiences you can have in life, especially if you move from one big city to another. Everyone wonders, “Will I fit in here in Chicago?” and “Will my lifestyle change?” I wondered the same things when I moved here from New York City.

At HotSpot, we want to be sure you settle into your new apartment easily and that you enjoy life in Chicago. To give you an idea of what to expect when relocating, I’ve asked Ashley, a 35-year-old NYC native, what it’s been like moving from NYC to Chicago.

moving from NYC to Chicago

Why did you move to Chicago?

“I moved to Chicago to be with my fiancé. We have dated long distance for our entire relationship, and when we got engaged, we needed to decide where to live. While I LOVED living in NYC, we decided that Chicago, where Christian has lived for the past 12 years, made the most sense for us long term.”

How long have you been in Chicago?

“I’ve been in Chicago for about a month and a half.”

Had you visited before?

“Yes, many times, especially over the past two years!”

What is the biggest difference you have noticed so far?

“The city is MUCH smaller but cleaner and less crowded – more spacious. The apartments are also so much more spacious!”

What do you miss most about NYC?

“The energy of NYC and fast-paced environment – both a blessing and a curse.”

What do you like about Chicago more than NYC?

“The cost of living. It’s nice that it’s not nearly as crowded. It’s nice to not always have that super fast pace! Also, they sell wine everywhere.”

What one word sums up Chicago based on your experience?


Favorite thing to do in Chicago so far?

“So far, I’m still in exploration mode – spending time outside! Checking out the restaurant scene, summer street fests, etc. Looking forward to concerts in the park and going to the beach!”

Favorite restaurants you have tried so far?

“Mott Street and Clever Rabbit.”

Are you a sports fan? Which sport? Which team?

“Not die hard, but I enjoy going to baseball games. I’m a Yankees and Cincinnati Reds fan. I lived in Ohio until I was 12. So far I’ve been to two Cubs games, so I think they will become my adopted team.”

Did you have friends here when you moved here?

“A few, not very many. Working on making some new friends, which can be challenging as an adult, particularly without a job, but everyone I encounter is super welcoming and friendly.”

What neighborhood did you end up moving to?

“We moved to Wicker Park.”

Do you have any pets?

Chloe and Charley

“We have two dogs. I brought my Toy American Eskimo, Chloe, here from New York, and my fiancé has a Britney Spaniel, Charley. Chloe is enjoying having much more greenery!”

What were the main goals of finding your place in Chicago?

Walking Chloe and Charley

Finding a place that’s big enough for two people, two dogs, and would enable us both to work from home. Eat-in kitchen with an open counter. Lots of natural light!”

How was the price of rent compared to New York?

“Significantly less expensive! Our 3 BR is 16% more than my 1 BR in Brooklyn and is on par with what a 1 BR would cost in some parts of Manhattan. Apartments are MUCH bigger. It took me some time to adjust to the amount of living space we now have.”

Do you notice a difference in the cost of living?

“YES! Everything is significantly less expensive, from groceries, dining out, gym memberships, etc.”

Where do you work?

“I quit my job to move here because my role [legal technology sales] was territory-based. My former clients are all in the Northeast. I’m still looking for my next gig.”

If you could give advice to other New Yorkers who are moving here, what would you tell them?

“Don’t have the expectation that Chicago is going to be a smaller, cleaner version of New York. I’ve heard this description from multiple people, but the cities and cultures are COMPLETELY different.

If you have allergies, be prepared for allergy season. They didn’t affect me nearly as much in the concrete jungle that is NYC. There are a lot more trees and greenery, even in the more urban neighborhoods in Chicago.

Also, don’t forget to bring bags with you when you go shopping to avoid the bag tax. I’m still working on remembering that one!”

If you could clear up one thing about New York for Chicagoans, what would it be?

“I think one of the biggest misconceptions is that New Yorkers are rude. I completely disagree – it’s just a different culture that is blunt and straightforward. New Yorkers are direct and don’t have time for nonsense. We have no problem stating our opinion. It’s a super-crowded, fast-paced city, and there’s a blurring between public and private life that breeds an unspoken sense of familiarity and community. There’s no need for superfluous pleasantries or beating around the bush. Everyone is in the same boat of needing to get stuff done, and we all share that mutual understanding.”

Do you have any personal stories or interesting anecdotes to share with our readers?

“I recently met a girl who asked if I wanted to do a hot yoga class with her, and my response was ‘No, I don’t like being hot.’ She was taken aback, laughed out loud and said, ‘I love the directness,’ as if she was expecting me to say maybe or yes, even though I had no interest. Thankfully, she didn’t take it as being rude, and we agreed to do pilates at a normal temperature.”

What Dorothy Learned About Moving from NYC to Chicago Today

Like Ashley, I also grew up in New York, and I was kind of curious to see what a new transplant would say. I’ve lived in Chicago for 17 years, and I completely relate to the misunderstanding that people share about New Yorkers. I realize that I have softened up a bit on directness, but maybe that’s okay. I wouldn’t trade my time in NYC for anything, but I LOVE Chicago, and I’m excited for Ashley and Christian as they get started on their new journey.

If you’re considering a move to the great city of Chicago, now is the perfect time. We have plenty of gorgeous luxury apartments ready for lease, as well as some new ones on the way, so contact us at HotSpot Rentals to see what we have to offer. We’d love to help you find you that new Chicago apartment you’ve dreamed of!