Pros and Cons of Living in Chicago from a REAL Local!

There are some obvious pros and cons of living in Chicago, but you don’t really know unless you’ve lived there for a while. Chicago isn’t just my hometown. I boomeranged back to where I came from after college, left, then returned for a while with my then-boyfriend Brian.

Then I left again for sunnier pastures. Now I’m nomadic, but I’m back home often enough that the allure of Chicago has returned, despite its faults.

Why can’t I just quit Chicago for good? For me, the pros and cons get pretty blurry. The blah stuff that has always bugged be about the city gets complicated when you start missing friends and family you left behind.

Let’s dig into it all, the pros of living in Chicago and the cons of life in Chicago.

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The Pros and Cons of Living in Chicago

I keep this one updated pretty often because there’s so much trash out there on this topic. Can you believe there are bloggers out there who will wax on and off about all of the pros and cons of moving to Chicago after just a visit here?

They blow in, eat their deep dish, sit in traffic, and claim to know the place.

Honey pies, you have no idea.

Below, check out some benefits of living in Chicago plus reasons why someone like me, a hometown girl, would want to leave, even if it’s temporary. These are all in good fun, and I love the city regardless.

Pro: The weather you experience prepares you for life anywhere else.

If you’ve experienced a bad Chicago winter followed by a bad Chicago spring, you are stronger for it. I used to laugh at girls in San Diego in their fuzzy boots when the temperature dipped to the low 60s.

Then I pulled my blanket up over my ears while I was shivering on the couch because Southern California did quite the number on me. I may not own those same fuzzy boots, but I have acclimated to mild weather year-round, thus making me a wuss when I’m somewhere that’s experiencing real winter.

It’s sad.

A real conversation I had with my husband one night in San Diego was re: the thermostat. He claimed it was 72 degrees in the house, but I argued that the thing must be broken because my extremities felt like they had just done the polar plunge.

Con: The same weather you’re enduring can get pretty bad.

Brian and I moved in together during one of Chicago’s “snowmageddons.”

My father-in-law was visiting from Minnesota at the time to help us out, and was, as a result, snowed in with us. I was a teacher at the time, and we had our first round of snow days since the 1980s. We were all expected to work from home, and businesses were shut down. Whoa, that sounds familiar.

That was just that one winter.

When Brian and I were planning to move to San Diego, we got a lot of this: “But won’t you miss the seasons?”

Do you mean the one where you don’t see the sun for three months or the one where you think things are finally warming up until a snowstorm comes through and dashes any positive feelings you were feeling?

Oh, you mean summer, when the humidity is so intense that riding public transportation is like sharing a sauna with anyone who happens to be riding along with you at the time.

But autumns are so crisp, right?

Wrong. This isn’t New England.

You get two days of fun foliage until the leaves fall into the gutter, followed by rain and flooding due to said leaves in the gutter.

Pro: You have decent public transportation.

My friends who are still in Chicago may not agree with me here, as Chicago’s public transport does have some work to do.

When you’ve lived somewhere that is so car-centric like Southern California, you miss being able to just hop on the train to get somewhere. This is despite the acts of public indecency I’ve witnessed and the smells emanating from some of its passengers.

Fun fact: It’s urine, by the way. That smell is urine.

San Diego had a bus system, but I never wrapped my head around where those buses went. There was also a trolley, I guess. It was just easier to drive around there, and I hated that.

Driving often means looking for parking, which in turn means parallel parking, which I’ve yet to master.

I’d much prefer a Blue Line train to ride downtown courtesy of the Chicago Transit Authority (CTA) and the “L,” pee smell and all. The city’s interconnected public transportation system will always be one of my top pros of living in Chicago.

In fact, Chicago’s network of buses and trains is one of the largest public transportation systems in the country.

Con: The traffic is always bad.

When I’d drive up to Los Angeles, which I tried not to do too often, I would get flashes of how bad traffic was in Chicago, no matter the time of day.

Despite the access to public transportation, the expressways are always bad. You need to add at least a half hour of padding to your driving time when you have firm plans.

Add regular road work on the main routes to and from downtown and the situation becomes even more insane. It’s difficult to even use any of the usual map apps as your guides, as the time just keeps changing with the worsening traffic.

Fun fact: Did you know that the term “gaper’s delay” is a Chicago invention? Also known as “rubbernecking,” it’s when people are causing even more traffic by slowing down and staring at nearby accidents on the road while they’re driving. It doesn’t matter which side of the road the incident is on, they’re all lookin’.

Pro: The food scene is awesome.

Chicago isn’t only about all the pizza — there’s more than deep dish pizza there, people — and all the hot dogs and all of the Italian beef.

I mean, it is those things, but it’s also all of the other things.

Whatever cuisine you can think of, you can find it in Chicago.

Actually, you could probably find several different eateries boasting whatever kind of food you’re craving, especially Polish food. Chicago still has a high population of Poles, so my people are slinging pierogi all over the place. San Diego, sadly, had limited options when it came to my motherland’s cuisine.

Outside of the diversity of food options, Chicago has long been on the foodie scene in terms of its wealth of celebrity chefs. 

Chicago has the fancy and the casual, the inventive and the comfortable. If you’re here to tick things off your bucket list, Chicago is home to Alinea, one of the best restaurants in the world. If you watch The Bear, you may know all of this already.

I’d argue that Chicago has the most delicious food in the country. Sorry, everyone else.

Con: The food will haunt you.

This isn’t really a con, but I need to reiterate the fact that the food in Chicago is really good. When you call that moving company and leave for somewhere like San Diego, home of the fish taco, you will miss the food from Chicago.

The food in San Diego is great, but nothing there is as good as the best of Chicago.

Is there a lot of crappy food in Chicago? Of course there is. We weed those eateries out pretty quickly, though. There’s just too much competition.

Pro: It’s cheaper than New York City.

Chicago is cheaper to live in overall than some of the big metro areas around the country. In fact, it doesn’t even crack the top 10 most expensive cities in the United States if all of those lists are to be believed.

People who live in Chicago may balk at that when they wave their mortgage statements for their homes and gas prices in your face, but it’s true. It’s just not as expensive in Chicago as any of the big hubs in California or the East Coast.

Now, a lot of this comes down to where you live in Chicago and what you do while you’re there. It costs more to live in desirable neighborhoods and eat designer pluots. Those are a plum and apricot hybrid, and they are delicious.

Con: It’s still expensive to live in Chicago.

San Diego was very expensive, but we paid what’s called a sun tax while living there.

In exchange for one of the highest costs of living in the country, we received plentiful days of sunshine that put everyone in a better mood when looking at the monthly credit card statements.

If we stayed in Chicago and pursued home-buying in the neighborhood we wanted — somewhere that’s walkable, with easy access to public transportation — we wouldn’t be paying a ton less for real estate than we did in San Diego.

At the time, we figured we’d overpay to live a place where you can jog on the beach in February.

I’m not jogging on the beach in February or any month, really, but it’s something people did there because of that plentiful sunshine.

Note: The property taxes in Illinois are also out of control, higher than any other state outside of New Jersey. Sales tax in the city is higher than the national average, too.

It just costs a lot to exist in Chicago, especially if you like to eat all of the things. Can you do it more cheaply? You sure can, but you’ll be compromising somewhere.

Pro: It’s a transportation hub.

Living in Chicago pros and cons lists should always include the city’s accessibility.

We could get around pretty easily from the airport in San Diego, but it often involved connecting through Los Angeles International Airport. That deserves its own opus on terrible airports around the United States.

Say what you will about Chicago’s O’Hare International Airport, but you can get anywhere you need to go from O’Hare, and often non-stop. Chicago Midway International Airport on the city’s south side is another option, especially if you’re a fan of Southwest Airlines.

For someone who loves travel and flies on the regular, being close to a transportation hub is crucial. For many, that accessible airport will top their list of reasons to live in Chicago.

Con: The city has its problems.

This is one the biggest reasons not to live in Chicago for many casual observers.

Some of the stuff you hear about Chicago is probably unfair. I’m not talking about the historical crimes of famous Chicago gangsters, like Baby Face Nelson and John Dillinger.

In modern times, most people who visit the city will never experience the Chiraq of it all.

That also points to the segregation that exists there, though. There are certainly Chicago neighborhoods that feel the effects of gang and gun violence daily, with a higher crime rate overall.

There are parts of Chicago where people are consistently struggling with unemployment, access to services, and inequity in the public schools there.

I started my teaching career in the Chicago Public Schools and went on strike within weeks of my first real teaching job. The level of need there is intense, and it affects what living and working in Chicago feels like for many of its residents.

There are also neighborhoods that are far removed from all of that. I lived a very privileged life there and grew up comfortably middle class. We had some issues with gangs in the neighborhood I grew up in and some light drug dealing, but I never witnessed any kind of violence there.

Chicago is a big city with big city problems.

Pro: Chicago is pretty darn scenic.

It may be considered a part of flyover country, but there are areas in the city of Chicago that beg a stopover, instead.

Explore Lake Michigan and some of its less populated beaches. Stroll through Lincoln Park, the actual park, not just the neighborhood, and enjoy the city’s iconic green space. Marvel at Pilsen’s murals. Find the best Chicago Instagram spots along the Chicago River and beyond.

The Chicago Botanic Garden is lovely, and yes, “The Bean” in Millennium Park, or Cloud Gate more officially, is worth a stop, too. Look around you while you’re there and take in the world-class architecture.

There’s plenty in the city that’s not quite so pretty, like that drunk guy outside of the bar in Wrigleyville, but there’s so much beauty if you look a little harder.

Con: The dibs system is hilarious until you need a parking spot in January.

Every winter, residents in Chicago collectively lose their minds and parking becomes way more intense than usual.

It’s called the dibs system.

Imagine this: You just spent an hour shoveling out a parking spot, so that you’d have one waiting for you when you returned from wherever it is you have to go to as part of your adult responsibilities. That’s hard work.

To make sure no one parks in that spot that is covered in your sweat and tears, you place any kind of furniture, upside-down garbage cans, or whatever else you have around your house that could withstand the elements to mark that spot.

You’ve called dibs on that section of the neighborhood.

The problem is, say you had to park blocks away already when you came home the night before. Or you’re unable to shovel. It can be quite a frustrating situation, and it lasts for months. But it continues because it’s a tradition at this point.

Note: I have no dog in this fight. We had a garage or off-street parking whenever we lived there long-term.

Pro: You will never run out of things to do.

If the weather is garbage in Chicago, visit a museum. The city is a hub for culture and the arts, and one of the best places to catch a live comedy show. Go eat or drink something delicious.

If you’re lucky enough to be enjoying a beautiful summer afternoon, there’s likely a festival or farmers market available to you whatever weekend you’re looking to fill.

If you’re bored in Chicago I’m worried about you.

Con: The FOMO is real.

Chicago comes alive on nice weather days. They just don’t happen too often, so people lose their minds a little. If you suffer from that fear of missing out in the slightest, a nice weather day will activate your FOMO unless you do something about it.

This is how I get talked into al fresco dining when I really don’t feel like putting real pants on, Sometimes I find myself deep into a pitcher or margaritas on these days when I don’t even really like margaritas.

I’m more of a sangria gal, honestly.

This isn’t a problem if you’ve embraced the art of saying no, but for pushovers like me, it becomes a problem.

Pro: Chicago sports are great.

Chicago is a bigtime hub for arts and culture, but it’s also a huge sports town. I’m lucky to say I’ve lived through a World Series championship for the Chicago Cubs, my preferred baseball team, and a world series for the Chicago White Sox, that other team.

I grew up watching the Chicago Bulls with my dad during the Michael Jordan era. I was there when the Chicago Blackhawks won a Stanley Cup.

If you don’t think the Chicago sports scene isn’t exciting, you must be a Bears fan. I’m joking, mostly.

Con: Chicago sports fans can be a lot.

Chicagoans are a passionate people. When our teams are doing well, everything is gravy in terms of Chicago sports culture. When our teams are struggling, we can become quite agitated.

You can ignore Chicago sports completely when you’re here, but if you’re moving to Chicago, you may find yourself swept up in the mayhem. Just let it happen. Ride the rollercoaster with us.

Pro: The city is diverse.

I’m not talking about the range of things to do here, although that’s definitely a big pro. I’m talking about the diversity in Chicago’s people.

You’ll find every ethnic group represented here. It’s a city of immigrants. My own parents decided that Chicago would be their new home after leaving communist Poland in the 1980s. Many Poles felt the same, and the city still has the largest Polish population outside of Warsaw in the world.

That all said, the city suffers from the same racial tensions as any other city in America, big or small. Our problems are just amplified, and the media coverage doesn’t help.

Con: Perceptions on crime are a distraction.

Even when crime in Chicago is down, as it is while I’m updating this post, my mom and people like her will say the city is at war. Yes, there are neighborhoods around the city that are perpetual targets for gun violence.

It’s a complicated issue that I don’t have the expertise to dig into here, but a lack of investment is certainly a piece of that problem.

Chicago is a talking point for many folks of a certain political persuasion who also like to use words like “woke” as an insult. Before you allow things to fly out of your mouth about my city, make sure they’re factual.

I always allow healthy debate when it’s based in reality, but if you’re spouting off nonsense that you heard because it feels right to jump on that bandwagon, you’re not welcome here. Do better.

Pro: The people there are quality people.

This is one of my favorite Chicago quotes from the city’s first female mayor, Jane Byrne: “Chicago’s neighborhoods have always been the city’s greatest strength.” 

Chicago, Illinois, feels like one big neighborhood. No matter how big it may seem, you’re always running into people you know, whether you want to see them or not, because you’re all probably hanging out in the same places.

There’s also loyalty among friends you make in Chicago. It feels like you’re all in this thing together.

You just don’t get that in big cities like New York City, or even in what became my adopted home in San Diego.

No matter how much time has passed, whenever I see my Chicago friends, they all seem genuinely happy to be with one another. I imagine they are.

People in California can be flakes. I’m not talking about the transplants we met while we were there, who were often from Chicago or the Midwest.

How do we all find each other, by the way?

I’m talking about actual Californians. They’re all living in the moment, with no time to reminisce about that time you used kitty litter to drive yourself out of a snow pile.

Oh. That doesn’t happen in California.

Whatever. It’s still a special moment shared amongst friends.

Pros and Cons: Living in Chicago FAQs

Is Chicago a good place to live?

Chicago is a good place to live if you give it a chance. Arrive with an open mind and you’ll see that this is a city of neighborhoods built by and for the people who call it home.

In my mind, the pros and cons of Chicago matter less than my connection to the city. Some of my favorite memories are deeply rooted in my life in Chicago. Chicago is a fantastic city, as long as you know what you’re getting into before you move.

Did I hate living in Chicago? Absolutely not.

The Windy City is a vibrant place to be, and you’ll certainly never get bored. I plan on returning time and time again, and it will always have a piece of my heart. Will I come back? It’s a maybe right now, but it wouldn’t be a huge surprise.

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