Chicago Vs. Philadelphia: Which City Is Better to Live In?

Ossiana Tepfenhart
by Ossiana Tepfenhart

Chicago and Philadelphia are two American cities that are marked by a heavy influence from the blue-collar world. Both famous for being manufacturing and factory towns, these two cities are starting to get a new identity all their own. People are moving into them at record rates. But, is there one city that tends to be better for families than the other?

Despite the colder temperatures and gritty architecture, Chicago seems to be heading in a better direction than Philadelphia. Both have even crime rates and somewhat similar education outcomes, but Chicago has better wages, higher home prices, and better entertainment.

Moving to either city can be a pretty big endeavor, and it’s not a decision to be made lightly. Let’s talk about the perks and pitfalls of each before you pack your bags.

Which City Is Better: Chicago Or Philly?

Both Chicago and Philadelphia are great for families that want to have a simple, affordable, blue-collar existence. But, one might be better than the other. Which one is right for you will depend on a wide range of factors.

Quality Of Life

When it comes to the quality of life, we look at the overall happiness of residents. Most people agree that Philadelphia and Chicago both have pretty stable lifestyles. They also tend to have fairly blue-collar lifestyles for most people, though Chicago definitely has more of a corporate lean than most others. Neither Chicago nor Philly residents seem to have a major issue with depression, which is why we’re going to assume that this is a tie.

Winner: Tie

Cost Of Living

In terms of the cost of living, there’s a lot to suggest that both cities are poised to have a relatively high cost of living in the future. However, they tend to be pretty reasonable right now. According to the stats we found, Philadelphia has a cost of living that’s around 101, which means that it’s only 1 percent higher than the national average for day-to-day goods.

Chicago has an overall cost of living of 106.9, making it a slightly more expensive city than Philly. Even so, most people won’t really notice that much of a difference between the two. Philly wins by a hair.

Winner: Philadelphia

Housing Costs

Chicago is a city that has a rapidly-increasing real estate market price point, which means that most investors are starting to flock there. You can blame the dense urban jungle feeling of the place, or just assume that it’s due to the job market. Either way, it’s clear that Philly is the cheaper place to buy a home. That’s why we’re going to cede victory to that city.

Average Cost 1 BR Apartment$1,672$1,400
Median Home Price$153,400$229,100

Winner: Philadelphia

Job Market

I’m not going to lie. Philadelphia has a job market issue. Low wages, high unemployment, and over a fifth of the population living in poverty prove it. Unfortunately, Chicago isn’t much better. The city does have a slightly lower unemployment paired with better wages overall. The problem is that Chicago’s job market isn’t showing the same potential for growth as Philly’s does, which suggests that the place is at risk of a work slump. It’s rough.

Projected 10-Year Growth28.4%25.7%
Median Household Income$45,927$51,247
Median Personal Income$26,211$31,613

Winner: Tied


This is a bit of a hard thing to debate, really. Both Philly and Chicago are known for having friendly locals with just a little bit of a snarky attitude. There’s a lot of camaraderie among the locals in both cities, and for loving similarly delicious food. Both Philly and Chicago are what foodies would call “craft beer cities.”

Philadelphia, in particular, is famous for its craft beer scene. In some circles, they go so far as to try to reverse-engineer some of the brews drank by the Founding Fathers. Chicago, on the other hand, is more about nightlife and house music.

Winner: Tied.


Both Chicago and Philly have very active music scenes and art scenes. Most of the time, people associate Philadelphia with punk rock while Chicago tends to be associated with house and techno music. However, both can be the location of major concerts and festivals from time to time. It all depends on the music scene.

The one thing we’re going to note is that Chicago has a much more popular arts and foodie scene. They have one of the best molecular gastronomy restaurants in America, not to mention several Michelin-rated restaurants. Most people find Philadelphia’s historic reenactors to be enjoyable, but kind of lame after a while. So, we’re going to hand this award to Chicago.

Winner: Chicago.


Philadelphia has a pretty strong public transportation system, but it definitely needs it. This is considered to be the second-worst city to drive in, and the average commute time in the city tops 33 minutes. Chi-town, on the other hand, has a steadier commute but doesn’t quite have the infrastructure for mass transit that Philadelphia has. Chicago, surprisingly, has a shorter transit system.

Winner: Chicago


Both Chicago and Philadelphia are known for having an extremely balanced number of different demographics as well as an openly LGBTQIA+-supportive community. There’s only one major difference that you might see in Philadelphia versus Chicago. Chicago is primarily composed of white and Hispanic communities. Philly is primarily composed of white and black communities.

Overall, both offer a nice melting pot effect on your life. It’s a great thing.

Winner: Tied


Philadelphia is known for spending a small fortune on each student, to the tune of $25,000 a pop. The area has a high school graduation rate of 83.3 percent, making it a great place for people who want affordability and a better chance at life despite blue-collar upbringings. Chicago is about even when it comes to high school grad rates, with a rate of 83.8.

The real difference is that Chicago tends to have higher populations of college graduates than Philadelphia. Chicago’s 4-year college grad rate is 37 percent, while Philly’s rests at 27.1 percent.

Winner: Chicago


Philadelphia and Chicago are both cities that experience all four seasons, but how much they experience of every season can vary. Both Philly and Chicago have somewhat mellow summers, though Philly tends to have summers that are slightly warmer. Chicago, being further north, tends to have colder summers and springs.

In terms of winters, that’s the real kicker. Chicago has one of the more bitter cold winters in the United States, and snow is a pretty common occurrence. This means that you will be able to expect higher rates of snow. It’s the Midwest, of course.

Winner: Philadelphia

Crime Rates

Believe it or not, Chicago and Philadelphia can say something that is quite unusual. They both have nearly identical crime rates. Chicago’s adjusted crime rate is only 1 point higher than Philly’s according to BestPlaces. In a nutshell, they both are considered to be pretty high-crime cities.

Gang activity has been reported in both Chi-town and the City of Brotherly Love. However, there is some good news on both fronts. According to local sources, gang activity has been on a decline for ages.

Winner: Unknown

The Verdict

For the most part, it’s clear that Chicago has a lot more going for it at the moment than Philadelphia does. However, they both tend to attract similar types of people to their doors. The one big issue that most people have with Philadelphia is that the job market is lagging and that wages are low. However, that’s starting to change bit by bit.

Will Philly remain the same run-down town in the future? We really don’t think so. There’s a lot of great talent within the city’s limits, and that tends to be a good indicator that people will turn the town around. So while Chicago might win right now, it’s only a matter of time before you start seeing a major improvement.

Related Questions

Is Chicago a rich or poor city?

Chicago is a city that has long struggled with poverty, ever since the car industry slowly started to fade from view here. Currently, around 20 percent of the city’s residents live a lifestyle that is deemed to be impoverished by the United States government. Studies suggest that there are even higher numbers of families who are food-impoverished or otherwise financially unstable.With that said, many people would consider Chicago to be a middle-class-to-poor city in terms of the lifestyle of the locals. However, you can find people in every financial bracket here.

What foods should you try in Chicago?

Chicago’s culinary scene is nothing short of legendary, especially if you’re a major foodie. Their most famous dish is obviously Chicago deep dish pizza, which is more of a stew than a pizza. Other important foods to try include Chicago-style hot dogs, steak, Chicago saganaki, and jibaritos.Most of the foods that are associated with Chicago’s history will have a heavy Italian-American influence to them. Expect lots of meaty dishes that stick to your proverbial ribs. Chicago loves high-quality meat, and they are not afraid to cook it!

What foods should you try in Philadelphia?

Philadelphia’s food scene goes beyond Philly cream cheese, though cheese does play a central role in a lot of their food. Their most popular food items include Philly cheesesteaks (natch!), hoagies, and Philadelphia roast beef sandwiches. If you are a fan of the sweeter stuff, you can give water ice a try. Some parts of Philadelphia are also pretty well known for their cookies.In terms of drinks, you can always rely on Philly to give you an amazing craft beer. It’s a major part of their overall food culture, which makes sense when you think about how much  Founding Fathers loved their ales.

Ossiana Tepfenhart
Ossiana Tepfenhart

Ossiana Tepfenhart is an expert writer, focusing on interior design and general home tips. Writing is her life, and it's what she does best. Her interests include art and real estate investments.

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