Moving to Chicago? Here’s Everything Retirees Need to Know

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View from Lincoln Park of the Chicago Skyline.

15 minute read

What You’ll Gain From Reading This Article: This article provides a comprehensive understanding of the pros and cons of retiring in Chicago. To assist potential retirees in choosing a suitable location within Chicago, the article explores four major regions—North Central Suburbs, Northwest Suburbs, Western Suburbs, and Southwest Suburbs.

Many people who think about moving to Chicago picture shopping on the Magnificent Mile, riding a subway train, or perhaps eating a hot dog (with no ketchup!) at Wrigley Field. Even though all these things certainly happen in the Windy City, there’s more to Chicago than meets the eye.

The Chicago metropolitan area, nicknamed Chicagoland, spans more than 10,000 square miles and 14 counties in the city and beyond. The world-class city and its suburbs serve as a cultural hub for the entire Midwest. The region draws people from all walks of life, including retirees who want to live near a world-class metropolis.

Active adults choose to spend their retirement near the Second City for many reasons. An abundance of unique options for restaurants, shops, entertainment, music, art, and more present themselves to those who look. Plus, there are plenty of 55+ communities with housing options to suit the preferences and needs of any retiree. Some imagine Chicago as a crowded and stressful place. But the nearby suburbs offer a small-town feel while providing a gateway to everything the world-class city has to offer.

Ready to get serious about moving to Chicago? This comprehensive guide has everything retirees need to know about the pros and cons of living in Chicago.

Retiring in Chicago: Pros and Cons

Chicago Style Hot Dogs with Mustard, Relish, Tomato, and Onion


  • World-class arts, culture, and entertainment. From the Art Institute of Chicago to the Field Museum, the Windy City has no shortage of famous destinations. With museums, historical attractions, galleries, restaurants, flagship stores, festivals, concerts, events, and more, active adults can always find something new to experience in Chicago.
  • Abundant outdoor recreation opportunities. The city’s remarkable location on Lake Michigan and the Chicago River provides access to boating, fishing, swimming, watersports, and more. Throughout Northern Illinois, active adults can explore lakes, rivers, state parks, gardens, and trails.
  • Distinct neighborhoods and suburbs. Nicknamed the “City of Neighborhoods,” Chicago comprises 77 vibrant communities that each contribute to the area’s renowned culture and diversity. There are more than 100 villages and towns in the broader Chicagoland area, so active adults moving to Chicago can find the community that best suits their needs and lifestyle.
  • Convenient public transportation. Chicago has an impressive and accessible system of buses, elevated (“L”) trains, commuter railways, water taxis, and bikeshares. The Chicago Transit Authority operates the country’s second-largest public transportation system. Also, the high-speed Metra trains make it easy for suburbanites to spend the day in the city. There are also two international airports.
  • Retirement-friendly taxes. Those who retire in Illinois can also take advantage of tax breaks that help keep more money in their pockets. The state doesn’t tax retirement income from sources such as Social Security, pensions, IRAs, 401(k)s, and other retirement plans.


  • Higher costs of living. Compared with other areas of Illinois, the city of Chicago and its surrounding suburbs tend to cost a little more. The overall cost of living in Chicago trends 5.7% higher than the national average, according to BestPlaces. Although, this number can certainly increase or decrease in different suburbs.
  • Congested traffic and crowds. People flock to Chicago for business, entertainment, and travel, which brings crowds and traffic to the area. While the city provides ample public transportation, those who drive may have to contend with traffic. Residents also have to deal with constant construction that can create delays and urban congestion.
  • Cold winters. The four-season climate combined with the location on Lake Michigan means that Chicago residents endure cold winters. Residents tend to enjoy milder weather every spring and fall.

Chicago Climate

A sightseeing cruise on the river in Chicago, Illinois.

Chicago, like much of the Midwest, experiences four distinct seasons and sees a variety of weather throughout the year. The weather may not be sunny and warm every day, like other retirement destinations such as Florida, but the different seasons give each year a pace and break up weather monotony.

The warmest months from June to September see average temperature highs at 83 degrees, according to Weather Spark. Rain is common during these months. On average, each day has a 26% chance or higher that residents will need umbrellas. 

The coldest months from December to March tend to see low temperatures around 22 degrees. Snowfall is not uncommon during this time, but the city rarely sees more than a foot of snow every few years. 

Chicago is called the Windy City, but the name was first coined in the 19th century to describe politicians full of windy sentiments, not the weather. While the winds off Lake Michigan are often chilly and frequent, the average wind speed is only about 14 miles per hour throughout the year.

Due to the high walkability of Chicago and its suburbs, residents should expect to spend a fair amount of time outdoors. Many Chicagoans also ride bikes to reach their destinations or to see more of the city. The weather hardly reaches extremes. However, seasoned residents know to check the weather to be sure their clothing matches the changing conditions of any day.

One common place to explore by foot or bike is the Lakefront Trail in Downtown Chicago. It’s a series of parks lining the city on Lake Michigan. Many gardens, arboretums, zoos, art installations, and other outdoor attractions call Chicago home, but simply taking in the city’s world-famous architecture is enough reason to get outside. 

Chicago Taxes

Facade of the Continental Illinois Bank Building at South Lasalle street in Chicago.
Image provided via elesi /

The Windy CIty is known for a great many things, but active adults moving to Chicago may not know about the area’s taxes. Overall, Illinois has some advantages and disadvantages when it comes to taxes. Active adults should carefully consider these expenses when planning their potential budget. 

The Illinois state sales tax rate is 6.25%. When added to local sales taxes, residents can spend upwards of 10.25% when making a purchase. Also, additional taxes exist in Chicago that may not be present in most places, such as a 9%amusement tax on performances and shows. There’s even a $0.07 tax for every plastic checkout bag used at the grocery store.

While the Chicago area may not be the most tax-friendly place in the country, it’s certainly not the worst. Luckily, several tax exemptions for retirees can help alleviate some of the financial burden.

Chicago Property Taxes

The average property tax rate in Illinois is 1.73%. Cook County and the counties adjacent to it range from around 1.38% to 2.09%. The average property tax payment in these counties ranges from $3,681 to $6,285. Lake County has the highest payment in the state. While Illinois has one of the highest property tax rates in the country, active adults can qualify for some tax exemptions to offset the cost.

Chicago Retirement Income Taxes

Retirees thinking about settling down near Chicago can rejoice, as the state of Illinois doesn’t tax retirement income. Social Security, 401(k)s, IRAs, pensions, and all other types of retirement income are exempt from the state’s income taxes. While this isn’t the most important deciding factor for active adults moving to Chicago, the absence of retirement tax is certainly an incentive. 

Keep in mind: All income and salaries not considered retirement income will still be subjected to Illinois’ 4.95% income tax. This should be considered if you move to the city before you begin collecting their retirement funds as your primary source of income.

Chicago Tax Exemptions for Seniors

Seniors are eligible for several exemptions at both the state and local levels as residents of Chicago. One exemption is the General Homestead Exemption. This exempts up to $10,000 of property taxes in response to a home’s increase in its equalized assessed value in Cook County and $8,000 in contiguous counties. 

Active adults may also qualify for the Low-income Senior Citizens Assessment Freeze Homestead Exemption. This freezes the equalized assessed value of a senior’s home if their total income is $65,000 or less and they meet other requirements. This means a qualifying senior’s property taxes cannot be increased if they claim this exemption. 

Another exemption is the Senior Citizens Homestead Exemption. This allows persons 65 years and older to reduce their home’s equalized assessed value by up to $8,000 in Cook County and contiguous counties, thus lowering their property taxes. Those 65 years and older can also qualify for the Senior Citizens Real Estate Tax Deferral Program. This could eliminate all or some of the real estate taxes on their home. All in all, several tax exemptions and deferrals can be claimed by active adults looking to retire in Chicago.

Chicago Health Care

A woman jogging at the park area at Montrose Beach, with the Chicago skyline in the distance.
Image provided via Page Light Studios /

The Chicagoland area offers premier medical services and a great number of world-class specialists. No matter where you’re moving to in Chicago, nearby health care centers can tackle medical concerns, big or small. 

One such facility is Northwestern Memorial Hospital, which has been on U.S. News & World Report America’s Best Hospitals list for more than 12 years. This accredited institution has annually earned many awards for its wide range of medical capabilities and treatment options. 

Residents will also likely have a Loyola University Medical Center nearby. The institution has multiple locations around the city and its suburbs. Loyola Medicine prides itself on going above and beyond to not only treat the illness but the whole person. 

Another accredited health care center is Advocate Good Samaritan Hospital on the west side of Chicago. This hospital’s services and experienced staff help active adults in the area get quality care without traveling too far.

Where to Live in Chicago

With 77 neighborhoods in Chicago and more than 100 towns and villages in the surrounding area, active adults have no shortage of choices when moving to Chicago. Many retirees live in the suburbs because of the everyday conveniences and easy access to the attractions of Chicago. However, each region provides distinct lifestyles, attractions, and 55+ communities.

North Central Suburbs

A nature trail at Saddlebrook Farms in Grayslake, Illinois.

The North Central suburbs of Chicago include towns such as Grayslake, McHenry, Woodstock, and Crystal Lake. The area boasts the Chain O’Lakes, a 7,100-acre system of 15 lakes connected by the Fox River. Residents in this area enjoy boating, fishing, and other watersports. Also, residents can reach the shores of Lake Michigan in 25 minutes, O’Hare International Airport in 35 minutes, and both Downtown Chicago and Wisconsin in 45 minutes.

Some of the notable landmarks in the area include Six Flags Great America in Gurnee, Moraine Hills State Park in McHenry, and Illinois Beach State Park in Zion. Alongside local fairs, farmer’s markets, and festivals, annual events include the Lake County Film Festival, Northern Illinois Boat Show, and the Lake County Craft Beer Festival.

The small towns in the area provide a tight-knit community feel with walkable main streets. Woodstock may be known as a film location for the 1992 Groundhog Day film, but it also has a historic town square listed on the National Register of Historic Places. Near McHenry, active adults can find the Volo Automotive Museum, Stade’s Farm and Market, and Stonewall Orchard Golf Club.

The area features several sought-after 55+ communities. Saddlebrook Farms in Grayslake offers affordable single-family homes that range from 1,169 to 2,516 square feet. Also, the Del Webb 55+ community Grand Dominion in Mundelein features resort-style amenities such as a clubhouse, indoor and outdoor pools, and walking and biking trails. Additionally, at Andaré at Woodlore Estates in Crystal Lake, active adults can find low-maintenance single-family homes.

Northwest Suburbs

The outdoor pool at Sun City Huntley in Huntley, Illinois.

The Northwest suburbs consist of a network of well-known towns such as Huntley, Barrington, Schaumburg, Elgin, and Carol Stream. These suburbs of Chicago provide some of the most convenient access to the Windy City, with Metra train lines running through the area.

The area features scenic natural areas that include James Pate Philip State Park, Blackhawk Springs Forest Preserve, and Kishwaukee River State Fish and Wildlife Area. Local attractions include Fox River Trolley Museum, Ellwood House Museum, and Hickory Knolls Discovery Center. Also, there’s easy access to attractions north of Chicago, like Medieval Times, Top Golf, and Trickster Cultural Center.

Along with the world-class sports teams in Chicago like the Cubs, White Sox, Bulls, and Bears, those in the Northwest suburbs can watch the Schaumburg Boomers play baseball at Wintrust Field. The town of Hamilton Lakes hosts a yearly Scottish Festival and Highland Games with Celtic music, Scottish traditions, and a Highland dance competition. Also, Elk Grove Village hosts the Chicago International Dragon Boat Festival. Additional seasonal events include the Prairie Arts Festival, Elk Grove Rotary Fest, and Rolling Meadows Corn Festival.

If you’re an active adult moving to Chicago, Sun City Huntley should be your first stop to explore. It’s the largest 55+ community in the Chicago area with 5,489 homes. The age-restricted community boasts the largest clubhouse of any active adult community in the state with the 94,000-square-foot Prairie Lodge. Also, Saddlebrook Farms in nearby Grayslake features more than 100 acres of lakes and nature preserves on its scenic grounds. Additionally, Lake Barrington Shores in Lake County offers attached homes ideal for those who want to downsize.

Western Suburbs

Exterior view of a model home at Lincoln Prairie by Del Webb in Aurora, Illinois.

West is best is something heard around Western suburbs like Batavia, Sugar Grove, Oswego, and two of the largest towns outside of Chicago, Aurora and Naperville. These smaller suburbs provide convenient access to Downtown Chicago via Metra rail or I-88 with more affordable and down-to-earth communities. Also, the area is experiencing growing popularity among retirees, young families, and working professionals.

Many of the area’s landmarks and attractions center around the neighboring towns of Aurora and Naperville, which have a combined population of close to 350,000, according to BestPlaces. Popular things to do near Aurora include visiting the Phillips Park Zoo, walking trails or flying model airplanes at the Aurora West Forest Preserve, and visiting Raging Waves Waterpark. Residents can also enjoy the Naperville Riverwalk that winds along the DuPage River, the Naper Settlement outdoor museum, and Centennial Beach. 

Additionally, the expansive Morton Arboretum in Lisle blankets 1,700 acres with nature preserves, seasonal gardens, and hiking and biking trails. The Classic Cinemas Tivoli Theater in Downers Grove, a restored cinema from 1928, offers free refills on popcorn and soda. And golfers won’t want to miss Rich Harvest Farms in Sugar Grove, a course consistently ranked among “America’s 100 Greatest Golf Courses” by Golf Digest.

The Chicago retirement communities in the western suburbs offer a range of home types, amenities, and price points. Carillon Club is a gated 55+ community in Naperville with 778 homes. The well-established community hosts a full social calendar of activities, clubs, and classes. Lincoln Prairie by Del Webb is a new 55+ community in Aurora that will include 550 single-family homes upon completion. Residents will enjoy signature Del Webb amenities such as a clubhouse, indoor and outdoor pools, and athletic courts. In North Aurora, Lincoln Valley is an active lifestyle community with low-maintenance homes.

Southwest Suburbs

Exterior view of a home at Lago Vista in Lockport, Illinois.

Residents of southwest suburbs like Joliet, Tinley Park, Plainfield, Lockport, and Shorewood enjoy one of the most convenient locations to access Downtown Chicago and its southside. Four Metra rails serve the southwest suburbs, which means active adults can reach the city and Midway International Airport within 45 minutes.

Joliet, as the largest suburb in the area, features plenty of restaurants, local shops, and attractions. Built in 1858, the Old Joliet Prison offers historic tours. The Joliet Area Historical Museum displays interactive exhibits with local and state history. Also, the nearby Route 66 Raceway hosts regular races and events for motorsports enthusiasts.

Nature lovers can find plenty to explore in the southwest suburbs of Chicago, including sites like Channahon State Park, Pilcher Park Nature Center, and Orland Grassland. Residents can even reach two highly visited natural areas within one hour: Starved Rock State Park in Oglesby and Indiana Dunes National Park in Porter, Indiana. A day trip to the shores of Lake Michigan is always within reach for active adults who retire in the southwest suburbs.

There are plenty of 55+ communities to choose from for those considering moving to Chicago. Carillon is a well-established age-restricted community in Plainfield with world-class amenities such as a 32,000-square-foot clubhouse, a 27-hole golf course, and a woodworking studio. Located about 30 minutes from Chicago, Lago Vista in Lockport is a mid-sized gated 55+ community that offers a low-maintenance lifestyle thanks to a homeowners’ association (HOA) that covers lawn care and snow removal. And finally, Shorewood Glen in Shorewood offers single-family and attached homes, abundant amenities, and a social calendar coordinated by a lifestyle director.

If You’re Moving to Chicago, 55places Can Help

55places can help you with the longest country-county move or a relocation to another part of town. For active adults interested in moving to Chicago, we’ll connect you with a local real estate expert who can help you every step of the way. Contact us today and take the first step toward an active and fulfilling retirement!

Discover what’s next.

To learn more information or connect with a real estate expert, contact us today.

Can you spot the $207,744 difference between these identical homes?

Financing is the difference!

Get the details in The 62+ Loan Homebuyers Guide.

55places Mortgage is a joint venture between Mutual of Omaha Mortgage and
Details here.

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I agree that 55places and its affiliates, partner providers or agents may call, text, or email me about my inquiry, which may be made with automated means. I understand that my consent is not a prerequisite for buying a property. I may revoke my consent at any time by contacting Message/data rates may apply. I also agree to’s Privacy Policy and Terms of Use.

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About 55places

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