16 Pros and Cons of Living in Chicago, IL

Updated On October 9, 2023
Chicago, IL

Since 1833, Chicago has been part of the United States.

The interest in the city and its population has grown beyond everyone’s wildest expectations to make it one of the biggest cities in the nation.

With all of that popularity comes great things, like diversity, but also things like high crime. 

Stick with us as we go through the pros and cons of living in Chicago.

Chicago, IL
Chicago, IL

Pros of Living in Chicago, IL

1. Diversity

People from across the world find themselves in the middle of America for who knows how many reasons.

They bring with them culture and experience to share with others.

Chicago is attractive for the opportunity it brings and the openness to those who are not local.

The ethnicity breakdown is 48% European-American, 30% African-American, 8% other, 7% Asian-American, 6% Hispanic-American, and 1% Native American.  

2. Cultural Events

What goes along with a place full of diversity?

Activities!

There are parades, festivals, and fun all over the city all year long.

Ever heard of the famous green river in Chicago on St. Patrick’s Day?

Everyone gets into the festive spirit, whether you’re of that culture or not.

That makes Chicago particularly welcoming for people from all walks of life.

Being around such a culturally varied group means you probably also have a beautiful set of friends. 

3. Public Transportation

Because living in the city is so financially challenging, Chicago did what was right and invested in public transportation.

It is quite common for someone to work downtown and take a train from the suburbs.

The trains and buses feel safe and are generally pretty clean.

Being able to rely on the trains is also a benefit. 

4. Sports

Sports is what brings Chicago together.

There have been several world-class athletes to come out of the professional sports teams.

What are you going to do on a cold night in March, walk home in the snow or attend a basketball game with all your buddies?

In that sense, you can imagine sports help keep fans warm due to body heat.

Yes, that many people pack into venues, bars, restaurants, and other places just to watch.

These are top-notch fans, too. 

5. Architecture

Take a look around.

The skyscrapers that adorn the horizon are spectacular.

Many travelers come here to tour those buildings and see what it is like to lean forward from that height.

Sears Tower is one of the tallest buildings anywhere and going to the top to look out is a touristy thing to do.

A great spot to take it all in is Navy Pier.

While everyone is looking at the water, turn around and look at the city.

It truly is a sight to behold. 

6. Variety of Food

Any city that is home to the number of people that Chicago is would most definitely come with choices.

There are about 7,500 places to eat in the city that come from all over the world.

The food here is so sought after that there’s even a type of pizza dedicated to it called Chicago Deep Dish.

Whether it is Italian you love or something from a place you have never heard of, Chi-town has it all.

You can get something quick in corner shops or at food stands.

It is delicious.

7. Lake Michigan

For a city with few nature spots, bordering Lake Michigan is a great perk.

There are 26 beaches with access to the lake.

So, everyone is grabbing a towel during the summer for some sand and cool water.

Knowing that it is our one joy from mother nature, Chicago does an excellent job of keeping the water clean and inspected for quality.

The lifeguards on duty are some of the best in the world.

It is really a top-notch escape when the weather is good. 

8. Public Libraries

Unfortunately, much of the year is too cold to enjoy doing literally anything outdoors.

If it is not the wind slapping you with frozen air, the ice is making you fall.

Then, like an oasis in the desert, the library is available.

Warmth will reel you in but a plethora of reading material will keep you coming back.

Not only is it the richest source of inspiration in the city, but the libraries also have a ton of other resources that do not come in print form.

Exploring the world of the Chicago libraries is a treat in itself. 

Cons of Living in Chicago, IL

1. Cost of Living

Chicago is the third most populated city in the US.

With a demand that high, it is not surprising that achieving that goal would come at an astronomical price.

Because there are over two and a half million residents, space is limited.

Rent is unsustainable for most jobs without a multitude of revenue streams or a few roommates.

All space is limited, so shops have to fight to get great locations, and then that cost is pushed back on consumers. 

It should be noted that, while expensive, Chicago is more affordable than other highly populated cities.

2. Weather

There are many places in the world where living by water makes it a rather enjoyable time, weather-wise.

Chicago is not one of those places.

Winter is one of the harshest in the country.

Sometimes the snow and ice are so debilitating that people have to abandon their cars on the roads.

They are essentially stuck.

Frigid temperatures carry on much longer here than in most of the country.

When temperatures are warming towards 80 in the south, Chicago is going into summer with lows of 40 degrees. 

3. Parking

A hotel stay outside the city often comes with free parking.

Downtown hotels charge because of how limited space is.

Then, there is Chicago.

Expect no less than $60 to park for the evening in a hotel room.

That price can rise quickly as you drive around thinking there might be a better option.

It costs to do just about anything.

So if you find a parking spot that is less than that, take it immediately.

Not even eating at a restaurant will save you from having to park somewhere that will cost more than your meal.

4. O’Hare International Airport

To start with, it is a pro to be able to fly out from your home city and virtually get anywhere in the world you are trying to go.

The con about it is everything that is involved with flying before the plane takes off the ground.

Traffic in Chicago is bad enough.

Add that to people trying desperately to get out of town and you have a disaster.

Throw rough winter conditions in the mix and it’s all over.

We have not even gotten to the airport yet.

Security, long lines, and impatient flyers await.

5. Traffic

Speaking of traffic, Chicago is third in the nation for worst gridlock.

As great as public transportation is, you would think fewer people would be using their own cars.

Unfortunately, that has not had a big effect on dwindling the car population.

The reason is that Chicago is a wealthy city.

High-powered jobs are common and there is a lot of money to be made there.

So, people are more prone to take their car, even though they could get some work done on a train. 

6. Concrete Jungle

Everything in Chicago is gray. Skyscrapers are everywhere.

While that adds to the uniqueness of the city itself, it leaves little respite for a weary, city-heavy mind.

Most people like to have some time to escape into the wilderness, or at least be able to see some greenery.

Aside from St. Patrick’s Day, there is little to look for.

That’s not to say there is no escape, certainly not undermining Lake Michigan or Millennium Park, but it can be tough to be so boxed in.

7. Crime Rate

It is not totally out of the blue to say Chicago has an exorbitant crime rate.

Not only is that on par with most major cities, but this part of Illinois is famous for being infamous.

Back during the prohibition, mobsters ran the town in order to get booze for speakeasies.

Al Capone kept Chicago wild with gun battles during Elliot Ness’ reign.

As frightful as that was, it didn’t go away after prohibition.

Today, the crime rate is 67% higher than the national average.

8. Taxes

Part of what makes the cost of living so uncomfortable is the taxes.

Chicago has the highest sales tax in the US and the second highest property tax.

The fees that no one asked for do not stop there, either.

Let’s not forget they implemented a tax on streaming services that are found nowhere else.

Chicago has put together taxes on a bunch of random things hoping no one would notice that there is yet another way for the city to gouge everyone.

Chicago, IL
Chicago, IL

Pros and Cons of Living in Chicago, IL – Summary Table

Pros of Living in Chicago, ILCons of Living in Chicago, IL
1. Diversity1. Cost of Living
2. Cultural Events2. Weather
3. Public Transportation3. Parking
4. Sports4. O'Hare International Airport
5. Architecture5. Traffic
6. Variety of Food6. Concrete Jungle
7. Lake Michigan7. Crime Rate
8. Public Libraries8. Taxes

Chicago Safety Overview

READ THE FULL REPORT: Chicago Safety Review

Safety Index:
65
Chicago
  • OVERALL RISK: MEDIUM
  • TRANSPORT & TAXIS RISK: LOW
  • PICKPOCKETS RISK: HIGH
  • NATURAL DISASTERS RISK: MEDIUM
  • MUGGING RISK: MEDIUM
  • TERRORISM RISK: HIGH
  • SCAMS RISK: MEDIUM
  • WOMEN TRAVELERS RISK: MEDIUM

Frequently Asked Questions

How do they turn the Chicago River green for St. Patrick's Day?

Starting in the early 60s, the river was dyed green for a week around everyone’s favorite Irish holiday.

A group of plumbers kicked off the tradition and now locals look forward to it every year.

The time the river stays green has been shortened to a few hours, but it is just as emerald as ever.

Is jazz popular in Chicago?

The term jazz was born in this part of Illinois.

This upbeat form of music caught on big time and that has not slowed.

Today, there are over 225 venues for jazz in Chicago.

Why is Chicago the Second City?

Two reasons come up.

The first is in relation to the giant rebuild after the Great Chicago Fire of 1870.

The fire went on for days, destroying basically everything.

So, upon the rebuilding, it was a second city.

The other is about how Chicago cannot keep up with NYC.

Is Chicago the windiest city?

No, not even close.

The origin of the nickname has been forgotten by many over the years, but it didn’t have anything to do with the elements.

The wind was in relation to politicians and residents viewing them as being full of it.

Thus, “The Windy City” was born.

Is homelessness a problem in Chicago?

Yes.

The high rent and expensive goods cause many to be unable to sustain housing and a job.

It is not uncommon to find someone homeless but employed.

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