This Major Midwestern City Is an Ideal Home for Retirees Who Love to Travel

For retirees and pre-retirees with an itch to travel, few, if any, U.S. cities have more to offer than Chicago, often referred to as the “Crossroads of America.”

Home to two international airports as well as a major Amtrak hub, Chicago is ideally positioned for hopping on a plane or train and heading off to see the world. For those who’d like to stay closer to home, there’s also plenty to explore in the city and nearby towns, collectively known as “Chicagoland.” 

It’s a travel-lover’s dream, though not without a few cost and climate trade-offs. Here is what you need to know if you’re thinking about retiring to the Chicago area.

Travel Accessibility

Flights

O’Hare International Airport, on the northwest edge of Chicago and about 18 miles from downtown, is one of the world’s busiest airports. It’s currently served by nearly 50 international and domestic carriers and is a major hub for both American Airlines and United Airlines.

According to the Chicago Department of Aviation (as of May 1, 2025), O’Hare tallied:

• Approximately ​1,020 daily direct flights to 181​​ U.S. cities
• Approximately 126 daily direct flights to 67 international destinations

Midway International Airport, an older and smaller facility, is on the southwest side of Chicago. It’s 12 miles from downtown and is a hub for domestic travel, with Southwest Airlines as one of its major carriers.

According to the Chicago Department of Aviation, (as of May 1, 2025), Midway had:

• Approximately ​198 daily direct flights to 75​​ U.S. cities
• Approximately 8 daily direct flights to 9 international destinations

Most of those international flights are to Mexico.

Trains

For train lovers, Amtrak operates from Chicago’s classic Union Station, with routes that span out to every region of the U.S. In addition, there’s a plan in the works to create an Amtrak route between Chicago and Windsor, Ontario, where it would connect with the Canadian railway system VIA Rail Canada. That service is slated to debut in 2027.

While Chicago is a port city on Lake Michigan and popular for pleasure boating, it is not a major cruise ship destination. However, there are a limited number of Great Lakes cruises that originate in Chicago as well as from Milwaukee, which is a little over 90 miles to the north.

Cost of Living and Affordability

Chicago is a very diverse city economically, with people all across the financial spectrum—from extreme poverty to enormous wealth. Cook County, Illinois, home to Chicago, had median home values of $305,200, according to the most recent U.S. Census Bureau estimate. That was slightly higher than the national median of $303,400.

Payscale reports that the cost of living in Chicago is 14% higher than the national average, driven primarily by housing costs. The Economic Policy Institute’s Family Budget Calculator (which takes into account housing, food, transportation, healthcare, taxes and other necessities) estimates that a household with two adults and no children living in Cook County would spend $5,599 a month on average or $67,185 a year.

Taxes

For taxes specifically, the Tax Foundation ranks Illinois 37 among the 50 states for its overall tax burden (with no. 50 being the worst). That’s due primarily to its relatively high property and sales taxes, which rank 41 and 38 respectively.

However, Illinois’ income tax comes in at 13, due to its flat tax rate of 4.95%. The state also exempts common sources of retirement income, such as Social Security, pension benefits, and distributions from retirement accounts like 401(k) plans and IRAs. Chicago currently imposes no income tax of its own but receives a portion of the tax collected by the state.

So higher-income retirees might want to take note. Compared to some other states, those tax savings alone could probably cover a nice trip or two.

Lifestyle Considerations for Retirees

Chicago has enough world-class attractions that you might never want to leave. That includes theater, music, major art museums, parks, restaurants, and an assortment of still-authentic ethnic neighborhoods. The area is also home to major universities like the University of Chicago, on the South Side, and Northwestern, in the nearby northern suburb of Evanston.

The athletically inclined will find the city and its parks particularly well suited for warm-weather sports like running, biking, and tennis as well as cold-weather ones like cross-country skiing and snowshoeing (and you can usually count on plenty of snow). Softball is popular, too, and often played with an oversize 16-inch ball that has become a Chicago tradition. The sport even has its own dedicated museum in suburban Forest Park.

Spectator sports fans will have their choice of pro teams to root for—and sometimes commiserate with—including the Bears (football), Blackhawks (hockey), Bulls (basketball), and Cubs and White Sox (baseball).

To stay healthy for your travels, Chicago is well supplied with top-tier medical facilities.

Other Things to Consider

Chicago is a vibrant city with attractions to match every taste. Like all big cities, it has issues with crime, traffic congestion, and other civic problems, as well as ongoing financial challenges.

Its climate is not for everyone, either. As the University of Illinois at Chicago explains in a note to prospective international students: “You can expect hot and humid summers, rainy springs, brisk falls, and frigid, snowy winters.” Looking on the bright side it adds, “If you prepare yourself with adequate clothing and realistic expectations, living in a location with four distinct seasons can be a fulfilling experience.”

In other words, no one would mistake Chicago for a sunbelt retirement haven. In fact, retirees who can afford it will often maintain two homes and split their time between Chicago and a more temperate locale like Arizona or Florida.

The Bottom Line

Chicago is a popular travel destination in its own right and ideally situated for retirees who want to explore the rest of the world. Anyone who is considering Chicago as a place to retire would do well to visit it in all four seasons and possibly rent for a year or so before buying. While many retirees may decide it suits them perfectly, others will find the harsh winter weather to be more than they bargained for.