Boston and Chicago are both beautiful cities that offer a wealth of culture and history, and either city makes a great choice for a place to live.

However, both cities also have pros and cons, and taking each factor into account can help you pick the city that best suits you, your taste and your needs.

chicago vs boston city images


Key takeaways

  • Chicago is larger than Boston.
  • Boston is more walkable than Chicago.
  • Chicago has more traffic and longer commute times.
  • Both Chicago and Boston have moderate crime rates.
  • The cost of living in Boston is much higher than in Chicago.
  • Chicago has higher income and sales tax.
  • Both Chicago and Boston have access to several beaches.
  • Boston receives more rain and snow than Chicago.
  • Both Chicago and Boston have cold winters.
  • Boston has better options for outdoor enthusiasts.
  • Both Chicago and Boston have great school systems.

Size

Chicago is quite a bit larger than Boston. Boston is just shy of 90 square miles, although the greater metropolitan area is much larger. Boston has a population of about 689,000 people.

Chicago is 234.5 square miles in size and has a population of about 2.699 million people.

The size of either city can be a plus or minus, depending on what type of lifestyle you prefer. Boston has a smaller, more charming atmosphere and can feel less crowded.

It’s also faster to get across Boston simply because it’s smaller. However, Chicago offers more neighborhood options and also provides more restaurant, shopping, and entertainment options simply because it’s geographically larger.

Chicago vs Boston cities
Chicago vs Boston

Walkability and Traffic

Because it’s smaller in size, Boston tends to be a more walkable city than Chicago. Many people who live in the city can walk almost anywhere they need, so they may not even need to own a car.

People who live in Chicago can also walk to nearby areas, so owning a car isn’t always a must. However, Chicago is less walkable, and you won’t be able to reach every area, simply because the city is so large.

Because Chicago is so large and is home to so many people, traffic can also be a problem, especially during busier times of the day. Getting across the city can often be quite time-consuming.

Driving through Boston can also be difficult, but recent construction has cut down on traffic through the city, meaning it’s often easier to navigate, and there is generally less traffic than in Chicago.

Chicago river tour boat and skyscrapers
Chicago river tour boat and skyscrapers

Crime Rate

Both Boston and Chicago have a moderate crime rate. Boston is often thought of as a safer city, but both cities have areas that should be avoided, particularly after dark.

In general, as long as you avoid these areas, both Boston and Chicago are relatively safe. Boston does have lower crime rates when it comes to property crimes or violent crimes.

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Cost of Living

The cost of living, including the cost of housing, is much higher in Boston than it is in Chicago. For example, the average monthly rent for a one-bedroom apartment in Boston is $2,260, and the average cost of a home is about $400,000, although many homes are closer to $725,000.

The cost of a home does vary depending on what neighborhoods you’re looking at.

In Chicago, the average monthly rent for a one-bedroom apartment is about $1,100, and the average cost to buy a home is about $379,000.

On average, the housing market in Chicago is about 162% lower than in Boston, and the cost of rent is about 27% lower than in Boston.

The cost of groceries and utilities also tends to be slightly higher in Boston. However, Boston has a higher median household income.

Most households in Boston have an average annual income of about $71,800, while families in Chicago have a median household income of about $57,200.

apartment building

Taxes

Although the cost of living is higher in Boston, taxes are much higher in Chicago. Chicago has some of the highest sales and income taxes in the country.

You might save money on groceries, utilities, and housing in Chicago, but much of those savings can be eaten up by the city’s higher tax rates.

Beaches

At first glance, it might seem obvious that people living in Boston have easier access to better beaches. Boston residents can travel to Cape Cod or any number of vacation towns with beautiful beaches along the coast of Massachusetts, Rhode Island, New Hampshire, or Maine.

There are dozens of beach spots near Boston, and while some are just a short drive away, most of these beaches are only an hour or two outside the city.

Chicago, however, also has amazing beaches. Chicago sits on the shores of Lake Michigan, one of the Great Lakes. This gorgeous lake is massive, and its beaches are beautiful.

Because the lake is so large, its beaches offer almost everything that Boston’s beaches on the Atlantic Ocean offer.

The weather can be lovely, and the sand is the perfect place to soak up the sun, build a sand castle, or view wildlife.

Lake Michigan beach
Lake Michigan beach

Climate

Chicago and Boston each see both beautiful and miserable weather. Each city sees about 200 days of sunshine per year, so there will be plenty of time to enjoy the outdoors, particularly during the warmer months.

However, Boston sees more precipitation and usually averages about a foot more rain and snow than Chicago does.

Chicago, on the other hand, is known as the Windy City, and many days throughout the year are incredibly blustery. Wind can be mildly annoying on warm days, but on cold days, it can significantly increase the windchill factor.

These two cities both have harsh winters. In Chicago, winter temperatures are often between 20 and 36 degrees. Winter temperatures are slightly warmer in Boston, with some daytime highs sometimes reaching into the high 30s or low 40s.

Winter in Boston
Winter in Boston

Proximity to Other Cities and Getaway Locations

For outdoor enthusiasts, Boston is often the better choice because it’s located only a few hours, at most, from dozens of towns or locations that offer easy access to ski and sledding areas or hiking and mountain biking trails.

Boston is also located near several getaway locations in New England, including tourist towns such as Martha’s Vineyard, Portsmouth, and Salem, in New Hampshire, Vermont, Massachusetts, and Maine.

Boston is also only a short drive or flight from New York, Toronto, Philadelphia, or Washington D.C.

People living in Chicago can drive north and explore nearby Milwaukee. Grand Rapids and Detroit are also located nearby.

However, visiting other major cities takes a much longer drive or flight, as the area around Chicago is more spread out. People living in Chicago can also venture north to explore different hiking and mountain biking options, but winter outdoor activities are somewhat more limited.

Fishing options, however, do tend to be equal to or even better than fishing near Boston.

Illinois Route 66 sign
Illinois Route 66 sign

Politics

Both Boston and Chicago tend to have Democrat elected officials, and voters often lean toward more liberal politics in both cities.

Boston is even more liberal than Chicago, however, and Massachusetts is often thought of as the most liberal or left-leaning state in the country. Conversely, Republican governors are popular in Massachusetts.

Public Schools

Schools in Massachusetts, including the public school systems in Boston, are generally the top in the country. Boston is also home to the oldest public high school in the U.S., which is called the Boston Latin School, and the oldest public middle school.

The area is also home to several world-renowned private and charter schools.

After high school, Boston also provides options to attend some of the most prestigious universities in the world, including the Massachusetts Institute of Technology, Harvard, and Tufts.

Harvard University
Harvard University

Illinois also has excellent public schools. Overall, Illinois is ranked ninth in the country, and many of the state’s best schools are located in Chicago.

The Chicago Public School system features over 600 public schools, which include 11 highly selective magnet schools. The school district is the third largest in the U.S.

Like Boston, Chicago is also home to several prestigious colleges and universities, including Northwestern University, the Illinois Institute of Technology, and the University of Chicago.

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