Are you thinking about living in Chicago? You’re in good hands.

With a population of 2.7 million, there’s no denying that living in Chicago has its benefits, but does it live up to the hype?

I have been living in Chicago for the past 8+ years and was asked to share my experience. So today I’ll be sharing the good, the bad and the ugly of daily life in Chicago based on my own experience.

As you read this list, keep in mind that this is my personal list of the pros and cons of living in Chicago. Not everyone will feel the same way.

In any case, I hope you find it helpful. Let’s get to it!

Pros & Cons of Living in Chicago, Illinois

Note: This post is part of the Local Living Series, wherein locals share honest insights of living in a specific city through comprehensive pros and cons lists. If you’d like to reach out to the author directly with questions, please do so in the comments below and our team will ensure it gets to the right person.

First, the pros of living in Chicago

#1. The people

First and foremost, allow me to start with my favorite thing about living in Chicago — the people. I don’t know what it is, but I swear the people that live in Chicago are some of the kindest I’ve met.

I feel that Chicagoans are genuinely friendly and down-to-earth in a way that is not common in large cities.

When I first moved to Chicago, I was constantly lost (surprise, surprise) and can’t recall a single situation where I wasn’t approached by someone helpful and willing to offer assistance.

I’ve lost count of the number of helpful interactions I’ve experienced personally while living in Chicago!

Heads up! If you’re a millennial, you’ll find a lot of like-minded folks to befriend while living in Chicago because Chicago is considered one of the best cities in the country for millennials to live.

#2. The cost of living

Like most major cities, the cost of living in Chicago is higher than the national average. But when compared to other large cities, it’s easily the most affordable option.

I mean, Chicago seldom makes an appearance on lists ranking the most expensive cities in the country for a reason! You can actually enjoy living here because it’s not cost-prohibitive.

For example, there’s a lot of comparison between Chicago and NYC (both skyscraper cities), but the difference in cost of living couldn’t be more different.

According to CNN’s cost of living calculator, a $100,000 salary in Chicago is equal to $199,000 in New York City (that’s double!).

Housing alone is 238% more expensive in NYC than Chicago yet you’ll have access to all of the same amenities while living in Chicago.

I played around with the calculator for a while and the theme is the same, Chicago is much more affordable than other large US cities.

I’m guessing the harsh winters (we’ll cover those shortly) have something to do with the reasonable cost of living in Chicago. Regardless of the reason, you won’t find me complaining, that’s for sure.

#3. Cultural activities

One of my favorite things about living in Chicago is having access to a plethora of cultural activities every day of the week. In fact, Chicago ranks as one of the best cultural cities in America.

You’ll have access to world-class museums like the Field Museum of Natural History (which rivals the one in NYC) and the Art Institute of Chicago.

If you’re in the mood to catch a great performance you can have your pick from three epic theaters: Chicago Theater, Goodman Theater and Steppenwolf Theater (which is currently undergoing a $54M expansion).

Oh, and lest I forget, Chicago is known for having one of the best music scenes in the country.

Lollapalooza is a must for music fans, the Chicago Blues Festival is a clear crowd favorite, and the plethora of jazz festivals are bound to keep you entertained every season of the year, especially summer.

#4. The food scene

If you plan on moving to Chicago, one thing is certain — you’ll never go hungry.

When most folks think of foodie cities, I don’t think Chicago comes to mind, which is a pity considering the city currently ranks as the third best foodie city in the country. You read that right.

I can tell you from firsthand experience that it lives up the hype. You’ll have access to SO many interesting restaurants and cuisines while living in Chicago, I barely know where to start.

The diverse food scene is impressive, especially in terms of ethnic restaurants. Oh, and I would be remiss to overlook the famous Chicago deep-dish pizzas and loaded hotdogs perfected in this city.

Anyway you slice it, you will be exposed to an awesome food scene while living in Chicago.

#5. Chicago is a diverse city

Chicago is considered one of the most racially diverse large cities in America. Approximately 52% of the population identifies as white, and 29% identifies as black.

I love living in a diverse city because I’m exposed to customs and cultures I didn’t grow up around. I’ve found it fairly easy to befriend both native Chicagoans and recent transplants.

My friends circle has grown from being fairly homogeneous to more diverse and interesting — a huge perk of living in Chicago, if you ask me.

#6. The airport is top-notch

As an avid traveler, having access to a good airport was a major factor in my decision to move to Chicago.

And it seems like I’m not alone in this regard. Considering the amount of business being conducted in the city, a ton of folks fly into and out of Chicago on a daily basis so having an effective airport is non-negotiable.

There’s a handful of airports that serve Chicago, but the biggest one takes the cake — O’Hare International Airport.

Offering more than 220 nonstop flights, the O’Hare International Airport is the third busiest in the country — serving 83 million passengers in 2018 alone!

The effectiveness of Chicago’s airport is a huge perk of living in Chicago, especially if you fly often.

#7. Public transportation

It’s hard to find an American city that feels livable without a car, but Chicago is a rare exception. In fact, Chicago’s public transportation system is considered the 6th best in the country.

As you know, most folks loves to hate on public transportation, but nearly 91% of Chicago residents approve of the public transpiration offered, myself included.

Thanks to the CTA (Chicago Transit Authority), you’ll always be able to get where you need to without much fuss or delay.

When I first moved to Chicago I brought my car because my job was located downtown but I lived in the suburbs. Within one year of this arrangement, I decided to move downtown and ditch the car altogether because parking became too much of a hassle and I was satisfied with the CTA.

Also worth mention, the metro system is very effective at connecting the suburbs to the downtown core. So if you’re moving to a suburb of Chicago, I suggest testing out the public transportation for a year before deciding whether you want to keep your car.

Based on personal experience, living in Chicago without a car is a breeze.

#8. Housing costs

Considering the size of Chicago, housing is surprisingly affordable by big city standards. As of 2021, the median cost of a home in Chicago clocks in at $340,000.

Let me tell you, as someone that hails from New York, this price seems surreal.

But wait, it gets better. Chicago has the 4th highest concentration of Fortune 500 companies in the US (36 companies total). By and large, these jobs pay higher salaries, the average salary in Chicago is $72,000.

Between the reasonable home prices and decent annual salary, it’s actually possible to consider owning a home in Chicago — an achievement most city dwellers can’t even afford to dream about.

#9. The sports culture

Ready to hear the understatement of the century? If you’re a major sports fan, you’re going to LOVE living in Chicago.

Home to five sports teams (Chicago Bulls, Chicago White Sox, Chicago Cubs, Chicago Bears, Chicago Blackhawks) and 27 championships, living in Chicago is a great option for those that like to brag about winning sports teams!

#10. The city’s architecture is world class

Yet another unexpected perk of living in Chicago is the constant exposure to world-class architecture. I’ll be the first to admit I know nothing about architecture, but I can still appreciate an aesthetically beautiful building.

Thankfully there’s plenty to admire in Chicago.

The Great Chicago Fire of 1871 gave birth to a revolutionary idea that officially kicked off the modern high rises we see today — buildings constructed of steel rather than wood, imagine!

These buildings make up Chicago’s epic skyline, considered one of the best in the country.

Tip: One of the best ways to enjoy Chicago’s magnificent skyline is by boat, an experience I can’t recommend enough.

Cons of moving to Chicago

#1. Winters in Chicago are brutal

Let’s address the elephant in the room, shall we?

Winters in Chicago are brutal and I guarantee that you will hate living in Chicago as soon as the temperatures dip below zero, the snow sets in and Lake Michigan freezes over.

The perk of winter in Chicago? I swear it’s the sole reason housing prices are reasonable since most folks can’t commit to living in Chicago during winter. So I guess it’s not all bad?

I will also add that winter gets easier to manage after you live through one or two. You learn ways to cope, be it with expensive jackets or impromptu weekend trips to palm trees and paradise.

One thing I can’t recommend enough for folks moving to Chicago it to pick up one of these bad boys. My therapist recommended it ages ago to stave off depression during winter and I can’t imagine living in Chicago (especially during winter) without it.

#2. The traffic is a nightmare

Make no mistake, traffic becomes a part of your daily routine when living in Chicago.

In fact, Chicago’s infamous traffic is rated the third worst in the country, with drivers spending an average of 138 hours per year sitting in traffic.

You can expect trips to take 2-3 times longer during rush hour, which really starts to chip away at your quality of life, believe me (hence the reason I ditched my car and moved downtown).

What’s more, even though Chicago has great public transportation, some folks can’t imagine getting rid of their car. If you find yourself in this camp, allocate a lot of time to traffic.

#3. Limited access to nature

Before the hate mail gets stamped, recall that I’m sharing my personal list of the cons of living in Chicago. Chicago doesn’t offer much by way of outdoor recreation.

There, I said it.

I mean sure, we’re located on Lake Michigan, which is a treat, but lounging on the beach gets old after a time. Not to mention you can only do that a small portion of the year before the cold sets in.

Don’t get me wrong, I enjoy Lake Michigan, North Avenue and Oak beaches as much as the next guy, but I need more variety.

There’s a handful of hiking options but they all require a drive and rarely live up to the effort required. In my opinion, limited access to nature is one of the biggest cons of living in Chicago.

I will admit though, Millennium Park is one of the best urban parks I’ve ever come across.

#4. High crime rate

Chicago’s crime rate is a contentious topic. Half the residents will tell you it’s not as bad as the media portrays and the other half will tell you it’s still way too high for comfort.

So let’s focus on facts and statistics instead. But fair warning — these stats are grizzly.

In 2018, there were 561 recorded homicides in Chicago, nearly double the number of New York City, which has triple the population.

This doesn’t imply that the entire city is unsafe, rather there are certain pockets to avoid. You’ll need to do extensive research before moving to Chicago because crime is a factor.

Worth noting, I’ve been living in Chicago for 8+ years and haven’t had any scary encounters but I’m also hyper-vigilant and seldom hang downtown past midnight, especially solo.

#5. The flat landscape

I grew up around mountains and forests and I didn’t realize how much I’d miss a varied landscape until moving to Chicago.

If you’re a nature nut, you’ll need to drive quite a distance (2+ days) to get into mountainous territory. For me, the flat landscape gets dull over time and I find myself clawing at the wall several times a year in desperate search of some varied terrain and serious nature.

Moving to Chicago (Post Summary)

In sum, these are the honest pros and cons of living in Chicago, Illinois.

1. The people are kind
2. The cost of living
3. Cultural activities
4. The food scene
5. Chicago is diverse
6. The airport
7. Public transportation
8. Housing costs
9. The sports culture
10. Chicago’s architecture
11. The winters are harsh
12. The traffic is a nightmare
13. Limited access to nature
14. High crime rate
15. The landscape is flat

And there you have it my friends – a quick roundup of the pros and cons of living in Chicago. Don’t hesitate to reach out with questions or helpful comments for other readers.

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