Evening traffic trails in downtown Chicago

From sports to job opportunities to world-class attractions, the Windy City has a lot to offer. (Getty Images)

Chicago is calling. It may be for work or because you like the idea of living in a major city that’s not far from your Midwestern hometown. Or maybe you’ve been a lifelong Chicago sports fan – through good times and bad – and you love the idea of being a season ticket holder for the Cubs or the Blackhawks.

But if you’re unfamiliar with Chicago, adjusting to life in the the third-largest city in the U.S. by population may take more time than you think. Get ready for cold winters, a high cost of living compared to the rest of the region and plenty of attractions to fill your time.

[See: The Best Apps for House Hunting]

Should You Move to Chicago?

Chicago is known for its diverse job market, ranging from industrial manufacturing and shipping to finance, the arts and retail. But in an age where many companies are offering work-from-home options, your choice to live in Chicago should factor in everything else the metro area offers.

One major benefit is Chicago's relative affordability compared to other major cities, although it’s considered pricey for the Midwest. If your choice is between Chicago and cities like New York, San Francisco or Seattle, homeownership is likely to be achievable fastest in the Windy City.

“Somebody that’s just starting out … could buy and still be paying less than they would in rent,” says Todd Szwajkowski, a real estate broker and president of SwakeGroup at Dream Town Realty in Chicago, as well as president of the firm’s LGBT client services division.

Chicago is the place to be if you like four seasons, can handle the cold and are hoping to take advantage of world-class attractions that draw tourists from far and wide, but don’t necessarily get as crowded as spots in New York City or Washington, D.C.

How to Move to Chicago

If you have the ability to visit Chicago before you sign a lease or make an offer on a home, you can make a more informed decision about the ideal home for you and exactly where you want to live. Even if you can’t visit, working with a local real estate agent who has experience with people relocating to the area can be a big help.

A move to the Windy City is possible on any time frame, but in a situation where you have no deadline, take your time, says Maurice Hampton, president of the Chicago Association of Realtors and owner and managing broker of Centered International Realty Corp. in Chicago. “I would create a six- to 18-month timeline for myself to do some research on Chicago and maybe visit a few times,” he says.

Before putting down roots and taking on a mortgage, consider renting for six months or a year when you first arrive. “If you want to test the Chicago market, I highly suggest renting. Our rental market is very robust right now … (and) it may give you an opportunity to explore and get a feel for where you actually want to live,” Hampton says.

Here’s what you should know before moving to Chicago:

  • Summer is short and winter is especially cold.
  • The cost of living is all about perspective.
  • There’s a neighborhood that will suit everyone.
  • Don’t expect safety to be a problem.
  • Take the CTA instead of keeping a car.

[Read: Everything You Need to Know About a Pending Home Sale]

Summer Is Short and Winter Is Especially Cold

Summer in Chicago has a reputation for being warm and sunny without too many hot days. Chicago’s location on Lake Michigan also means you have waterfront attractions at Navy Pier, public beaches and fresh water as far as the eye can see.

However, summer weather averages about 100 days every year, and the winters are known to be cold. The average high temperature in January is a mere 32 degrees Fahrenheit, with average lows in December, January and February below 30 degrees, according to the National Oceanic and Atmospheric Administration.

Winter in Chicago is cold, and wind coming off Lake Michigan can make it feel colder, but investing in a warm coat will help make any time spent outside more comfortable. Hampton says there are some people who may decide Chicago isn’t the right fit because of cold winters, but it’s not hard to get by and enjoy the more temperate weather during the rest of the year.

The Cost of Living Is All About Perspective

How you view the cost of living and home prices in the Chicago area depends on where you’re moving from and where you want to live. If you’re moving from a major city like Miami or New York, Chicago will feel like you're getting the benefits of a major urban center at a discount.

If you’re coming from a smaller town or city known for its affordability, you may experience some sticker shock if you’re looking at townhouses and condos in the heart of downtown. The average rent in Chicago is $1,943, and the average apartment in Chicago is 749 square feet as of February, according to rental listing information site RentCafe.com. Norada Real Estate Investments reports the median home price in the Chicago metro area thus far in 2020 is $247,000.

Still, homeownership is achievable for Chicago-area residents at a variety of prices, and you don’t have to have a six-figure income to afford to buy. Szwajkowski recalls a charming one-bedroom condo in Rogers Park, a neighborhood in the northern part of the city, that recently went on the market for $99,900.

“There are some really low price points in some really nice neighborhoods – they’re just a little bit further out,” Szwajkowski says.

There’s a Neighborhood That Will Suit Everyone

Like many major cities, you have the choice to live in the heart of the city or seek more room in the suburbs. But Chicago’s sprawling city limits provide plenty of options, including neighborhoods with lots of single-family houses and a suburban feeling in an urban setting in addition to the high rises and upscale dining options of other parts of the city.

Check out the restaurants, businesses and local attractions that can make one neighborhood feel more like home than another. Szwajkowski says he often narrows down neighborhood choices, after factoring in budget and job location, by showing housing styles. “Pretend it’s a Rorschach test. Just respond, ‘Oh that’s cool,’ or, ‘I hate that,’” he says.

Even if you prefer a more rural setting, Chicago can still work for you. Hampton notes that he lives in the city of Chicago and is just a 40-minute drive from Beecher, Illinois, a small farming community with a quaint downtown and fewer than 5,000 residents.

“If that’s something that you want and you have an opportunity in Chicago, you don’t have to sacrifice the kind of life you want,” Hampton says.

Don’t Expect Safety to Be a Problem

For people who don’t live in Chicago or know many people who reside there, the only time they may hear about it on the news is after a violent crime has occurred. But Chicago is not any more dangerous than other major cities, and there’s no reason for you to have an elevated concern about crime in Chicago than you would anywhere else.

“I’m sure you’ll find that it’s not just Chicago, it’s not just New York and LA, it’s not just the U.S. If you watch global news, the world is in flux right now, from Belarus to London,” Hampton says.

[Read: Reasons to Buy a Condo – and Reasons to Beware]

Take the CTA Instead of Keeping a Car

Chicago has a robust public transit system of buses and trains run by the Chicago Transit Authority, or CTA. Chicago’s characteristic trains are referred to as the “L,” an abbreviation referring to the elevated platforms of the above-ground rail line.

Even if you live in a neighborhood well outside of the city center, L access is considered a reliable form of transportation, and you can get around town fairly easily without a car. Plus, you'll save on the cost of vehicle upkeep, insurance and parking if you stick to public transportation options, bicycling or walking.

Even as employers examine more permanent remote work options for employees, making a daily commute a less immediate factor in where to live, Szwajkowski says access to the L remains important for many homebuyers.


10 Ways Millennials Are Changing Homebuying

The generation that's taken over homebuying

Shot of an attractive young couple moving house

(Getty Images)

The Great Recession delayed many millennials from being able to buy a home, but the generation isn’t locked out of property ownership the way it was a few years ago. The National Association of Realtors defines the millennial generation as people born between 1980 and 1998, and according to the 2019 NAR Home Buyer and Seller Generational Trends report, they make up 37% of all homebuyers in the U.S., the largest share of any generation. Over the past five years as millennials have become a significant portion of U.S. homebuyers, they’ve also helped shape trends in location and home type preference, helped usher in technological advances and embraced new platforms that make a home purchase feel more user-friendly. Here are 10 ways millennials are changing the homebuying process.

Updated on Feb. 26, 2020: This story was published at an earlier date and has been updated with new information.

Text communication is key.

Text communication is key.

Young man texting from home in stylish apartment

(Getty Images)

The telephone was once the primary form of communication between real estate agents and their clients, but the younger generation that has grown up with internet and cellphones will likely prefer more text-based modes that make it easy to multitask. “A lot of my clients already work in tech, so their expectation is they’re going to work with an agent that can at least keep up with them in terms of communication,” says Dana Bull, a Realtor with Harborside Sotheby’s International Realty in Marblehead, Massachusetts, who specializes in working with homebuyers. She says millennial homebuyers prefer to text and email their agent more often than older generations, and it’s reasonable to expect they’ll be comfortable using real estate-related apps.

Research is a natural part of the process.

Research is a natural part of the process.

Cropped shot of an attractive young student working on her digital tablet at home

(Getty Images)

When it comes to researching neighborhoods, checking out listings online and doing a deep dive into the fine print of a pending deal, millennial homebuyers are known for doing their homework. Jill Levin, a Realtor with Coldwell Banker Legacy in Albuquerque, New Mexico, says she recently represented some buyers in a deal that went particularly smoothly because the buyers read every disclosure and document sent to them and asked questions beforehand – something she doesn’t see from older buyers who feel experienced enough that they don’t need to read into the details. “There’s way more information today now, and (homebuyers) really, really should be paying attention,” Levin says.

The hub for advice is online.

The hub for advice is online.

Unrecognizable woman uses a digital tablet to shop for a new home. She is reading information about a two story home in the suburbs.

(Getty Images)

While apps and online search tools are an integral part of the homebuying process for all consumers these days, millennials are the first generation to grow up using technology broadly in everyday life. The familiarity with smartphones, social media and the internet make communication, finding out information and contacting professionals easier. Millennials are also inclined to shop around for everything from real estate agents to mortgages to contractors. In HomeAdvisor’s State of Home Spending report released in June 2019, the majority of millennials, Generation X and baby boomers research home remodel project costs on the internet, but millennials do so by the largest margin (77%).

Homeownership is focused on building wealth.

Homeownership is focused on building wealth.

Young family stands outside of a new suburban home.

(Getty Images)

While purchasing a home involves plenty of hurdles for younger buyers, many of them are choosing to become homeowners because it helps them build wealth in the long term. “There is still interest in buying a house because I’ve got a job, I need a place to live, rent is expensive and I should put my money somewhere,” Bull says of the millennial homebuyer mindset. As they build equity in their home, they’re in a better place to purchase a larger house in the future or use the profit of a sale for other investments.

Kid-friendly housing makes a comeback.

Kid-friendly housing makes a comeback.

Children Helping Mother To Make School Lunches In Kitchen At Home

(Getty Images)

Homeownership isn’t the only thing that millennials are doing later in life for financial reasons. Millennials are also marrying and having children later than previous generations. But as millennials get older, more are getting to the point where they’re starting families. While a condo in the heart of downtown worked for many first-time millennial homeowners when they were single, home preferences change as soon as kids come into the picture, Bull says: “People are starting to step up into that next level of a single-family home and maybe out in the suburbs.”

Walkability is a must.

Walkability is a must.

Couple Walking Dog Along Suburban Street

(Getty Images)

Even with many millennials leaving urban centers, one feature they won’t compromise on is walkability. “They want more activities in the area, they want walkability, they want the convenience of shopping without having to use their cars a lot,” Levin says. Even in more suburban settings, many millennials are showing a preference for areas that offer residential and commercial spaces within walking distance. Bull says the areas catering to these homebuyer preferences have been dubbed “hipsturbia,” where suburban towns offer an active downtown or main street area with the live-work-play atmosphere many people don’t want to lose when they move out of a major city center.

Eyes are on garages and kitchens.

Eyes are on garages and kitchens.

Young bike commuter leaving garage.

(Getty Images)

Luxurious features and finishes in a house are ideal, but millennial homebuyers are making their must-have lists a bit more realistic. In a survey of 1,000 Americans who plan to purchase a home in 2020 by real estate information company Clever, millennials' preferred home features focused on details that make life more convenient, especially as they start families. When asked which features are a requirement for their new home, millennial respondents placed a garage, large kitchen and space to grow into as their top three priorities. Details like hardwood flooring, a fireplace, pool and dedicated office space were among the lesser-desired details.

High home prices don't deter eager buyers.

High home prices don't deter eager buyers.

Real estate agent with couple in luxury home. They are shaking hands. There is a water view, kitchen and living room in the background.

(Getty Images)

Affordability is still an issue for many millennials, especially among the younger members of the generation. But that doesn’t mean millennials are uninterested or afraid of purchasing a home – it’s just a matter of the right timing, the right location and the right home. Between consistently rising home prices and a lack of inventory as homeowners choose to remain in their homes longer, the housing market remains extremely competitive, Bull says, especially in the Boston area where she works. But the millennials who are financially ready to purchase are willing to rise to the challenge. “They’re used to being aggressive to get into the college they want, and then get the job they want,” Bull says, which primes them to make a strong offer if they see a home they like.

Low down payments solve savings issues.

Low down payments solve savings issues.

Happy couple at home paying bills with laptop

(Getty Images)

The Clever survey found 70% of millennial homebuyers plan to make a down payment of less than 20%. Low down payment programs have grown significantly in the past 10 years and are now a major part of home purchases – NAR’s 2019 Profile of Home Buyers and Sellers reports that the median down payment for a home in the U.S. is 12% of the purchase price. While low down payment programs help resolve the lack of savings, homebuyers putting less than 20% down should be sure to factor into their budget the added monthly cost of private mortgage insurance.

Parents play an important role.

Parents play an important role.

Shot of two men working on a project together at home

(Getty Images)

For younger millennials and even Generation Z, which is made up of people born in 1999 and later, coming up with the cash for a down payment is one of the biggest obstacles to becoming a homeowner, even at less than 20% of the purchase price. For millennial first-time homebuyers and the rare Gen Zer getting into the market, financial help from a loved one is often what makes a home purchase possible. “Parents are getting involved a lot – I still see a lot of situations where parents are gifting money or helping in some other way,” Bull says. “I don’t see that changing at all.”

Here are 10 ways millennials are changing homebuying:

Here are 10 ways millennials are changing homebuying:

San AntonioTexas suburban housing development neighborhood - aerial view with houses in rows in middle-class neighborhood

(Getty Images)

  • Text communication is key.
  • Research is a natural part of the process.
  • The hub for advice is online.
  • Homeownership is focused on building wealth.
  • Kid-friendly housing makes a comeback.
  • Walkability is a must.
  • Eyes are on garages and kitchens.
  • High home prices don't deter eager buyers.
  • Low down payments solve savings issues.
  • Parents play an important role.

Read More

Tags: real estate, Chicago, housing, housing market, home prices, new home sales, existing home sales, pending home sales, moving, renting


Devon Thorsby is the Real Estate editor at U.S. News & World Report, where she writes consumer-focused articles about the homebuying and selling process, home improvement, tenant rights and the state of the housing market.

She has appeared in media interviews across the U.S. including National Public Radio, WTOP (Washington, D.C.) and KOH (Reno, Nevada) and various print publications, as well as having served on panels discussing real estate development, city planning policy and homebuilding.

Previously, she served as a researcher of commercial real estate transactions and information, and is currently a member of the National Association of Real Estate Editors. Thorsby studied Political Science at the University of Michigan, where she also served as a news reporter and editor for the student newspaper The Michigan Daily. Follow her on Twitter or write to her at dthorsby@usnews.com.

Recommended Articles

How to Write an Offer Letter to a Seller

Tania Isacoff Friedland | Sept. 17, 2020

Connect with home sellers to make them feel good about letting you purchase their home.

The Guide to Understanding Home Value

Devon Thorsby | Sept. 15, 2020

Here's a look at the process of calculating the value of your home and what it means for your home's sale price.

How to Set Up Your Utilities

Devon Thorsby | Sept. 9, 2020

Here's what you need to know about which utility company services your new address, how to set up an account and why you may need to pay a deposit.

What to Know About the Halt on Evictions

Devon Thorsby | Sept. 3, 2020

The CDC has announced a halt on evictions through the end of 2020, but certain criteria keep some renters vulnerable to eviction. And the rent is still due.

How to Declutter Your Home

Devon Thorsby | Sept. 3, 2020

Follow this step-by-step guide to make your home more manageable and organized.

Deed vs. Title: What to Know

Devon Thorsby | Sept. 1, 2020

Learn how the deed and title play into homeownership, and the details you need to know before closing on a home.

Is Fee Simple or Leasehold Better?

Devon Thorsby | Sept. 1, 2020

Learn the different ways you can hold property with fee simple ownership or a leasehold.

How to Factor in a Home's Outdoor Space

Tania Isacoff Friedland | Aug. 27, 2020

While outdoor space has always been considered an appealing feature to homebuyers, there's newfound value in having a private outdoor oasis.

Should You Build a Mother-in-Law Suite?

Devon Thorsby | Aug. 25, 2020

These additional living spaces could give you the guest space or rental income you're looking for.

25 Small Space Decor Ideas for Your Home

Devon Thorsby | Aug. 21, 2020

These tips can make a small room feel bigger and help you master organization with minimal storage.

5 Things to Ignore on a Home Tour

Allison Chiaramonte | Aug. 20, 2020

Don't rule out a potential home for the wrong reasons. Focus on the details that count.

Why Tenants Are Not Safe From Eviction

Devon Thorsby | Aug. 19, 2020

People struggling to pay rent should still be worried about eviction should local eviction moratoriums end.

How to Vet a Neighborhood Before Moving

Devon Thorsby | Aug. 17, 2020

Before signing a lease or buying a house, visit frequently, check neighborhood safety and learn more about the area.

What Is a Duplex?

Devon Thorsby | Aug. 11, 2020

Learn the basics about duplex properties, and how they can be a first step for people looking to invest in real estate.

Should You Live in a Single-Family Home?

Steven Gottlieb | Aug. 11, 2020

Depending on your own priorities, finances and bandwidth, one style of living might be better for you.

Denver Housing Market Forecast

Andrew Fortune | Aug. 6, 2020

Here's what you need to know about the Denver housing market now, and what to expect in the future.

How to Make and Accept an Bid on a Home

Devon Thorsby | Aug. 6, 2020

Here's what you need to know to go under contract and move toward a successful home purchase or sale.

Considerations Before Buying a Vacation Home

Geoff Williams | Aug. 5, 2020

You'll want to think about money, rental challenges and market.

How to Build a Fire Pit in Your Backyard

Devon Thorsby | Aug. 4, 2020

Follow these 10 simple steps to transform your backyard into a rustic retreat.

What to Know About the LA Housing Market

Devon Thorsby | July 30, 2020

Before you try to buy, sell or rent in Los Angeles, know what to expect.