New York City VS Chicago VS Boston – Where Should You Settle Down?

One thing the world has no shortage of is places to live, which is why choosing where to live is one of the most crucial decisions a person has to make.

Whether you’re just starting your life or you’re looking to relocate, you have to choose a place that offers you what you need to live your ideal life.

Now, this might sound simple enough, but in reality, there is no perfect location to live in. Every place has its benefits and drawbacks.

The best option is to weigh the pros and cons of each location and choose the place that offers the most valuable benefits and the most bearable disadvantages.

In this article, we will present you with helpful information that will enable you to make an informed choice on the best place to live between New York City, Chicago, and Boston.

Related; Los Angeles VS NYC VS San Francisco

Brooklyn Bridge New York with skyline Manhattan

New York City

You would be hard-pressed to find a more iconic location in the United States than New York City.

New York City is arguably the most famous city in the world. This is no surprise, considering it is often referred to as the world’s capital city.

The Big Apple, as it is famously known, is the largest and most cosmopolitan city in the United States.

The city has beautiful scenery and is home to a thriving art and culture scene. 

It has many Must-See Attractions such as Times Square, The Statue of Liberty, Empire State Building and Brooklyn Bridge, one of the Famous Bridges In New York.

It is densely populated, and culturally diverse, with over 800 languages spoken in the city.

New York is home to hundreds of cultures and nationalities, all of which are thriving alongside each other, making it seem more like a country than a city.

New York City Manhattan urban city skyline and skyscrapers buildings

New York City Skyline

Besides having an iconic skyline, New York City is a financial center and a cultural hub and its five boroughs have a place for everyone.

It has a reputation for being the sample megacity and attracts thousands of new residents annually.

In NYC you can find almost any amenity known to man. There is little that you can’t access in the city, at any time of the day or night, whether that is restaurants, grocery stores, movie theaters, and so on.

The cost of this is having to deal with nearly 19 million, often noisy people who you’ll have to compete with for affordable housing and parking spaces. There will be moments where you feel overwhelmed by the experience.

With a population of 8.2 million over 469 square miles and a metro population of 19.9 million, you’ll either love or hate New York, rarely do you find people on the fence.

New York City Weather

New York City weather is very unpredictable. It changes randomly from day to day, and sometimes the city experiences erratic weather changes within a day.

However, after living there for some time, you can almost predict what the weather will be like on any given day.

During spring, the city comes alive with nature. The trees are green, and flowers bloom freely and abundantly. Residents experience light rain and gentle winds and the weather drifts between cool and warm.

In summer, NYC is generally sunny and sometimes quite hot. Its sunsets arrive later than usual and cool, refreshing winds sweep through the city.

New York City Weather


Fall is quite cold but not unbearable, though it is advisable to wear warm clothing – several layers, as you find comfortable.

Winter is often chilly and snowy, though not significantly colder than fall. You can also expect some warmer days, though not nearly as warm as summer.

New York City Weather 1


Cost of Living in New York City

New York City is notorious for its high cost of living. This is largely due to its high rent costs.

However, there are ways to reduce your cost of living significantly, such as taking advantage of its sophisticated public transport system.

To live a comfortable lifestyle in NYC, a resident would need to earn around $82,500 annually.

New York City Housing Costs

New York City Housing Costs


As mentioned earlier, New York City is known for its high cost of living and this is largely due to its high rent prices.

Currently, the median rent in New York for a one-bedroom apartment is $2,045 and $4,152 for a two-bedroom.

To deal with the high cost of rent, residents often partner up with roommates to reduce the cost. However, this is not the safest option, neither is it the most convenient.

If you choose to go for a co-living situation, you should be thorough when vetting potential roommates and ensure you choose someone or people you can trust.

It is also helpful to apply the standard rule of three before choosing a place to rent. This means you should be earning at least three times your monthly rent, before taxes.

Transportation in New York

Transportation in New York


New York’s transportation system is one of its highlights. As costly as rent and housing are in the city, its sophisticated public transportation system makes living there completely worth it.

Besides having a comprehensive public transport system, it also offers the advantage of running 24/7.

This is the primary reason New York is famous for being the only city in the US where a majority of households do not own personal vehicles.

Most New York residents commute to work and other places by public transportation, biking, or walking.

Transportation in New York 1


On average, NYC residents spend around $4,303 on transportation costs annually.

Though this depends largely on whether public transportation is the primary method of transportation.

If you purchase a 30-day unlimited MetroCard, you should spend no more than $127 for unlimited access to the local buses and the subway.

This adds up to about $1,524 per year. So there is great utility in using the public transport system as a primary method of transportation.

The downside is of course overcrowding. NYC’s population means long delays and heavy traffic congestion.

To combat this, you will need to plan your daily trips so that you can leave the house early and arrive home on time.

New York City Healthcare Costs

Before moving to any city, it is necessary to consider the cost of healthcare. The average cost of healthcare in NYC is $2,779.

For a family of four, the expected cost should be $7,924. New York City is home to many city-operated health clinics that offer free or low-cost healthcare.




Chicago is the third-largest city in the US, behind NYC and Los Angeles. While New York City is a haven for culture, Chicago is a more residential city.

Its affordable living costs and reliable public transport system make it the perfect place to start your big city living experience.

Chicago is home to many skyscrapers but the city is also brimming with nature.

It features over 600 parks and the iconic Lake Michigan which is within walking distance from downtown Chicago.

Chicago 1


Like New York, which is famous for New York style pizza and Brooklyn style pizza,  Chicago is also famous for its cuisine, and most of all, for their pizza.

The deep-dish Chicago-style pizza is iconic in its own right and many would argue that it is better than anything New York could offer.

Generally considered to be the best food city in the US, those who choose Chicago over New York will not be lacking in cuisine.

Not to mention that accessing food and other services is much easier in Chicago since you won’t have to deal with the huge crowds and high prices due to surges in demand for the most trivial things.

For those who prioritize a healthy work/life balance, Chicago is a great choice.

Unlike New York which has a highly competitive job market and requires residents to constantly be in a hurry, Chicago residents can have a more relaxed and balanced approach to work, providing space for other valued activities.

Chicago residents enjoy less traffic, shorter commutes, and a much better public transport system.

Chicago has a population of 2.7 million over 234 square miles and a metro Chicagoland population of 9.5 million.

The population density is 11,847 people per square mile.

Chicago Skyline

Chicago Skyline

The Weather in Chicago

Like every other city, living in Chicago has its downsides. One of these is its often brutal weather.

While it lacks weather extremes like earthquakes and hurricanes, Chicago’s weather can be very frustrating for residents.

The city is prone to long, harsh winters and scorching hot summers. Residents only have spring and autumn to look forward to.

Winter in Chicago is long and brutal. The windchill can get as low as minus 40 degrees and the city sees an average of 36 inches of snow a year.

The Weather in Chicago


Cost of Living in Chicago

To live comfortably in Chicago, we recommend a household income of about $51,360 a year.

Chicago Housing Costs

Housing in Chicago is quite decent compared to the other cities in this article. You can have much more space at similar costs to that of New York City and Boston, if not less. The median rent for a two-bedroom is $2,160.

Co-living with roommates is a great way to make rent in Chicago even more affordable.

And as homeownership continues to increase in the city, the price of rent will keep dropping.

If you are going to move to Chicago, you should consider homeownership.

Home prices in Chicago fall below the national average, meaning that it could be more affordable to purchase a home than to pay rent.

Home prices in Chicago


Transportation in Chicago

Public transportation is an affordable and pragmatic option in Chicago, though it is not as sophisticated as that of NYC. About 30% of Chicago residents use it regularly.

The city’s public transit system is extensive and it covers a lot of ground.

Its 30-minute transit trip is the largest in the country. It also helps that 98.5% of jobs in Chicago are located within half a mile of public transit.

Chicago transit, though quite reliable, can be stressful for those who commute from one end of the city to the other, daily.

There are few east-west train lines, and these trips can be very long trips for those who use public transport.

Transportation in Chicago


Traveling by railway costs about $2.50 per ride, and for those who would rather travel by bus, you can budget $2.25 per ride.

A Chicago Transit Authority monthly pass is $105 and gives you access to unlimited travel on buses and trains.

The city’s flat terrain and well-designed sidewalks make it perfect for those who choose to walk their way around the city.

The street grid is easy to follow and makes it near impossible to get lost.

Other facilities make walking around the city a pretty straightforward ordeal. These include pedestrian bridges, trails, and linear parks.

It is also great for those who prefer to cycle. Chicago is home to over 248 miles of protected and conventional bike lanes.

It is not uncommon to see these bike lanes filled with cyclists during busy hours. Bike-sharing is also a popular option in the city.

Transportation in Chicago 1


Healthcare Costs in Chicago

Healthcare in Chicago is affordable but the price is nothing special. The estimates for healthcare will cost $2,862 per year for a single full-time working adult and $7,460 per year for a family of three.




Like NYC, Boston is rich in culture and opportunities. It is often considered to be the perfect alternative to living in NYC, especially for those who aren’t fans of the hyper-busy city life that NYC is all too famous for.

Boston blends the best of big-city and small-town living. It offers a serene environment while maintaining the perks of urban life.

Despite having a significantly smaller population than NYC (689,000), Boston is a very active city.

Bostonians are always heading somewhere and taking advantage of the many opportunities available in the city.

The city is home to various industries, and companies such as Google, Microsoft, and Amazon.

Those who are seeking jobs in fields like tech, science, and finance will find Boston quite valuable.

Boston 1


Like Chicago, Boston is a very walkable city. Its public spaces are structured so that residents and visitors have no problem moving around on foot, whether that means going for a stroll or heading to work. The city is pretty easy to navigate.

Boston is also a beautiful city with gorgeous architecture and a very popular cultural scene.

It is brimming with nature and despite being a coastal city, its beauty can be enjoyed through all four seasons.

Boston Weather

Boston Weather


Boston experiences chilly and snowy winters but some winter days are blessed with warmth.

Its spring days are warm but sometimes rainy and as expected, nature comes alive in beautiful ways.

During summer, the weather is often warm and sometimes scorching, but for the most part, it is pretty pleasant.

Like New York City, the weather can be quite unstable, though it experiences significantly less rainfall. Heavy rainfall is typically reserved for fall.

Cost of Living in Boston

Boston is one of the most expensive cities to live in anywhere in the world. The average cost of living in Boston for one person is $2,899 per month. Making it between 48% and 62% higher than the national average.

Most estimates suggest that you need a household income of $120,900 to live comfortably in Boston.

This figure largely depends on how many bedrooms you will be renting.

Boston Housing Cost

Boston Housing Cost


Housing in Boston is unusually expensive. The Boston housing market is around 300% higher than the national average.

The median home price in Boston is $717,943 and the cost of rent is not encouraging either.

The median monthly rent for a two-bedroom comes in at around $2,249 per month. This means a significant portion of your monthly salary will go towards paying rent.

Not to mention that the average utility bill is 17% higher than the national average.

As far as housing goes, you’ll need to be pulling in about six figures to comfortably afford housing in Boston.

Transportation in Boston

  Transportation in Boston


Transportation is also quite expensive in Boston and costs around 31.8% higher than the national average prices.

This includes mass transit fares, gas, car insurance, and maintenance costs.

You will also need to factor in an annual parking fee, which varies between $135 per month and $530 per month.

Like in New York, you can save thousands of dollars by taking advantage of the public transportation system.

For $90, you can access a monthly LinkPass that offers you unlimited trips on buses, the subway, commuter rails, and ferries.

Healthcare Costs

Healthcare costs in Boston are 36% higher than the average national prices. The average healthcare costs for Boston residents are:

Doctor’s visit: $149.68

Dentist visit: $128.59

Optometrist visit: $140.26

Prescription medication: $596.23

Veterinary visit: $66.81

Side by Side Comparisons  

CITY Rent (one bedroom) Rent (two bedrooms) Cost of Buying a House Transportation (public) Health Insurance Utilities per month Recommended Annual Income
NYC $4761 $6188 $571000 $127 $713 $162 $82,500
CHICAGO $1025 $1413 $299,000 $89 $589 $132 $51,360
BOSTON $1875 $2600 $615,000 $90 $564 $147 $120,900


Choosing which of these cities to visit or relocate to depends on your budget, annual salary, and environmental preferences. For a more peaceful and affordable lifestyle, Chicago seems to be the obvious choice.

However, if you can afford it, Boston and NYC both offer great opportunities for work as well as more exciting cultural experiences.

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