Honest Pros and Cons of Living in Chicago From a 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, and then returned for a while with my then-boyfriend Brian.

While I’ve since left (and returned) a few times, the allure of Chicago remains as an option for a permanent base for us when we’re ready, despite its faults. Let’s get into all of it, the good, the bad, and the delicious about life in Chicago.

Living in Chicago at a Glance

• Best for: Food lovers, city people who like diverse neighborhoods, travelers
• Biggest pros: Food scene, transit, culture, walkability
• Biggest cons: Winter, taxes, traffic, cost creep
• Good to know: Winters are long, summers are elite, crime is neighborhood-specific

Pro: Chicago weather prepares you for life anywhere else.

It’s hard to describe what it’s like in Chicago without talking about its winters.

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.

READ MORE: Winter in Chicago can be fun, though. Steal my guide to my favorite winter activities in the city.

Con: Chicago winters can be brutal.

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 snowed in with us. I was a teacher then, 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.

That was just that one winter. Harsh winters are common in Chicago.

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 are you talking about 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: Chicago has reliable public transportation.

My friends 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 as car-centric as Southern California, you miss being able to 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 understood 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: Chicago traffic is a challenge.

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 access to public transportation, the expressways are always bad. You need to add at least half an 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 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: Chicago has an incredible food scene.

Chicago isn’t only about all the pizza — there’s more than deep dish pizza there — 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 some 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: You’ll miss Chicago’s food when you leave.

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.

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

Pro: Living in Chicago is cheaper than in 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 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. Housing costs are higher in desirable neighborhoods, and when you’re eating designer pluots from the fresh market.

Those are a plum and apricot hybrid, by the way, and they are delicious.

READ MORE: You can find more affordable rentals in neighborhoods like Humboldt Park, home to one of the city’s best green spaces.

Con: The cost of living in Chicago can be high.

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 our finances.

If we stayed in Chicago and pursued home-buying in the neighborhoods we wanted, we’d still pay quite a bit without the benefit of all that sunshine. It’s likely something within our price range would require some home improvement, too.

We were lucky enough to have two nice incomes while living and working in Chicago, so it felt more affordable. We also don’t have children, which makes life in Chicago easier on the wallet.

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: Chicago is a major transportation hub.

Pros and cons lists for Chicago 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 nonstop.

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: Chicago struggles with inequality.

This is one of 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 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.

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.

Some neighborhoods 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 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. That’s why Chicago is always worth visiting and a big reason why many consider moving here.

Explore Lake Michigan and some of its less-populated beaches. (I’m not talking about North Avenue Beach. That one is always busy.) 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 isn’t so funny when you need a parking spot.

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

It’s called the dibs system, and it’s one thing that’s only funny when you don’t have to deal with it.

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. That’s hard work.

To make sure no one parks in that spot that is covered in your sweat and tears, you call dibs. 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.

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 like The Art Institute of Chicago, one of the best museums in the country. The city is a hub for cultural activities 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 is at its nicest on warm-weather days. They just don’t happen with regularity, 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 has an amazing sports culture.

Chicago is a big 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 is exciting, you must be a Bears fan. I’m joking, mostly.

Con: Chicago sports fans can be intense.

Chicagoans are a passionate people. When our sports 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: Chicago is a diverse city.

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. Living in Chicago is like living in a few different cities, all at once.

You’ll find every ethnic group represented here. It’s a city of immigrants. My 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: Chicago crime perceptions can be misleading.

Even when crime in Chicago is down, 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 debate when it’s based in reality, but if you’re spouting off nonsense because it feels right to jump on that bandwagon, you’re not welcome here. Do better.

Pro: Chicagoans are loyal and community-minded.

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 living feels like you’re part of 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 when winter comes, and you’re wondering why you live in Chicago.

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.

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.

Who Should Not Move to Chicago

Chicago isn’t for everyone. If you see yourself in any of these categories, think twice before packing up your life:

• Sunlight-dependent humans: If a week without sun makes you feel like a wilted houseplant, Chicago winters will test your survival skills.
• Heat-averse people: I talk a lot about the winters, but summer humidity can make even short walks feel like mini-saunas.
• Winter-averse folks: There it is. If the idea of months of snow, wind, and sub-zero mornings makes you shiver just thinking about it, Chicago winters will test you.
• Fans of quiet suburban bliss: Some Chicago neighborhoods are calm, but most come with that city buzz you’ll either love or hate.
• Expecting New York energy: If you’re looking for non-stop hustle, 24/7 nightlife, and the “always on” vibe of NYC, Chicago is a bit more laid-back.

FAQs About Living in Chicago

Is Chicago a good place to live?

Chicago can be a very good place to live, as long as you have all of the information in front of you.

If you’re wondering whether you should move to Chicago, start with the pros and cons. Spend some time in the city without an agenda to really get an idea of what it’s like living in Chicago.

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 more permanently? It’s a maybe right now, but it wouldn’t be a huge surprise.

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