Chicago vs. New York: A Simple Sparkles Comparison

Having lived in both New York and Chicago (and now the suburbs of Chicago!), I’m often asked which city I like better or what the major differences are between the cities! This is particularly true right now as I prepare to go on a business trip to New York with several of my born-and-raised Chicago colleagues!

I really struggle to answer both of those questions – for me, New York and Chicago represent very different times in my life.

In New York, I was really focused on my career and my friends. I moved there just out of college, worked at the same company for five years – really building a name for myself and a relationship with many of my colleagues. I had amazing personal and professional experiences in New York, and met truly wonderful people; however, something was always missing.

Enter: Chicago. When I moved back to Chicago, for me, it was really an expression of what was truly important to me in my life – family. I went from being about 1,000 miles and two plane rides away from my parents and much of my extended family – to being less than 200 miles and a 2 hour car ride away. Not only that, but Chicago gave me the opportunity to find (and marry) my husband, and we were able to begin to build our family. I’ve had both wonderful and not-so-wonderful career experiences in Chicago – but they’ve all been less significant in my life because I was living with the close foundation of my family.

Now, I should say that this was my personal experience. I know many people who have or have built amazing family foundations in New York… and many people who truly focus on and build their careers in Chicago. But, for me, my experience/life really switched focus when I moved.

So, with this personal lens in mind, I’ve tried to outline what I see as the major differences/comparisons between the two.

Reflected Chicago
Reflected Chicago” by Roman Boed / CC BY 2.0
New York - Skyline by Daxis
New York – Skyline” by Daxis / CC BY-ND 2.0

Chicago vs. New York: 5 Things to Think About

1. Things to Do

Both New York and Chicago have wonderful museums, parks, theaters, shops, bars and restaurants. I think anyone could truly spend weeks, months and years in either city without running out of things to do!

I think that New York may slightly edge out Chicago in terms of theater and comedy  shows (at least stand-up comedy, obviously Chicago has Second City, a sketch comedy incubator!) – just by sheer number of venues and options.

For shopping and bars/restaurants, I think New York’s big advantage is walk-ability (at least in Manhattan) as things in Chicago are a little bit more spread out, and a more extensive transportation system. But being able to walk a lot of places or take a subway isn’t necessarily an advantage for everyone, and, in my opinion, while Chicago traffic isn’t great, I would MUCH rather drive in Chicago than in New York. So here, to each their own!

Both cities truly have amazing restaurants and food options, so which is better probably comes down to personal preference, symbolized by the age-old debate between Chicago and New York style pizza! 🙂 In my opinion, New York may have slightly better Italian restaurants (pizza aside) and some lesser-known cuisine choices, but Chicago has better Mexican and Indian options (again, totally my opinion and based on my restaurant experiences).

2. Work/Career

For me, I associate the most career growth and career-focused part of my life with New York. I had amazing opportunities and mentors that really pushed me out of my comfort zone and encouraged quick professional development. However, part of that is due to the fact that my field – public relations/communications – is very much focused in New York and a lot of our clients (healthcare companies) are based on the east coast.

That being said, I know that Chicago is also an epicenter for business. I hate to sound like a broken record, but again, I think it depends on what business you’re in (and potentially what stage of life!).

3. Environment

For this one, I think Chicago is a clear winner. While Central Park in New York is fantastic – you can go blocks and blocks in New York without seeing anything green. In Chicago, from my experience, you have not only Millennium/Grant/Maggie Daly Parks (all connected for those of you who aren’t familiar with Chicago), but also a lot more tree-lined streets and parks. Not to mention, Lake Michigan! (Yes, I know New York has water as well, but Lake Michigan is breathtaking, and I feel like it’s cleaner…)

Not to mention, New York in the summer seems to exist under the misty odor of garbage on the street… Not pleasant!

4. Livability

Again, in terms of livability, I feel like Chicago is in the front. A lower cost of living in the city and more accessible/affordable suburbs give Chicagoans more options and more expendable money. I will caveat this because I’m personally a lot more familiar with the Chicago suburbs and transportation than I was with New York. But I’m backed up by some statistics since Chicago is America’s 7th most expensive city and New York is the 1st (with only a slight difference in income!).

5. Energy

This is a very vague and abstract concept, but I think one of the most important things (at least to me) when choosing favorite locations to visit or to live is how a city (or any other location) makes me feel. From my perspective, New York is filled with a frenetic energy that makes you want to create or achieve something. Chicago, on the other hand, is grounded in purpose with a solid energy and consistent flow.

I’ve used this analogy with many people – and to be honest, I’m not sure where I first heard it, but I’ve since adapted it a bit. Chicago is a city that, if you give it a hug, will hug you back. New York on the other hand will give you a giant push.

So which city is right for you really depends on whether you’re looking for a push or a hug. Which one you’re looking for may change over time!

For a more concrete comparison between Chicago and New York, check out the below infographic from CityPASS!
Chicago and New York - What's the Difference

About Lindsey

Hello! I'm a 30 year old, newly married, lady living outside of one of the best cities in the USA! I work in communications, love to read, recently purchased an RV with my husband (yay for road trips!) and am looking forward to starting a family soon-ish. I love to smile and hope to make other people smile too!

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