Retiring in Chicago

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Chicago is a wonderful city to call home for people of all ages and lifestyles. If you’re considering retiring in Chicago, you are not alone – 14% of the Chicago metro population is over 65. So why are people retiring in Chicago? Chicago is a cultural hub with excellent healthcare and transportation options. Learn more about why so many people are retiring in Chicago.


cloud gate millennium park
Cloud Gate in Millennium Park / Courtesy Chicago Department of Cultural Affairs and Special Events

Chicago’s unique culture attracts visitors and residents alike. The city offers plenty to do in all seasons with some of the best museums, restaurants, and beaches in the country. Top museums include the Art Institute of Chicago and Field Museum of Natural History, but Chicago is also home to a number of equally fascinating museums devoted to the history of people from many cultures who immigrated to Chicago. With numerous theaters and galleries, you’ll have something to do every night of the week!

Chicago is filled with plenty of restaurants serving up delicious international fare. As a melting pot for numerous cultures, Chicago allows you to eat authentic Chinese dumplings for lunch and Polish kielbasa for dinner.  

If you need a break from the big city, there are plenty of weekend getaways or day trips near Chicago to satisfy your curiosity. Plus, Illinois is home to a number of wineries and apple orchards that make for a relaxing trip. You may not even need to leave the city – Chicago has many beautiful parks to get back in touch with nature.

Public transportation

Chicago transportation on the L
New Washington Station / Courtesy of Transit Chicago

Many people don’t consider transportation when choosing a retirement destination. However, transportation frequently becomes a problem due to medical issues that arise during retirement. Thankfully, transportation isn’t a problem in Chicago, which has trains, buses, bike shares, taxis, and is the 6th most walkable city in the entire country. Chicago boasts the 2nd largest transportation network in the United States – right behind New York City. So, while you can own a car in Chicago, there is really no need to.

The gem of Chicago’s metro transportation system is the skyline train called the “L” by residents. The “L” operates 24 hours a day on eight lines with over 100 miles of track. This network is supported by a bus system that enables over 1.64 million people to ride Chicago public transportation each weekday.

Chicago is also extremely bike-friendly, with over 200 miles of bike lanes and a bike share system in place. Of course, Chicago also has plenty of cabs and shared ride services like Lyft and Uber.

If you love to travel, you’re in luck – there is quick rail service to both major airports in Chicago. If you’re planning a trip in northern Illinois, you may just want to hop on the Metra. The Metra train system has over 1,155 miles of track providing service to 81.6 million passengers yearly. It’s an excellent option to get to a quick lunch appointment in a nearby town or to explore Illinois.


Another important ranking factor for retirement destinations is local healthcare. Chicago is a leader in US healthcare and has several hospitals that rank nationally for geriatric care: Rush University Medical Center and Northwestern Memorial Hospital. Both hospitals have nationally recognized geriatricians – specialists in managing the health of people over 65 – who treat incontinence, heart disease, diabetes, and memory loss. With over 90 hospitals in the Chicago metro area, you are always close to great healthcare.

In addition to hospitals, there are plenty of primary care doctors and health care services in Chicago focused on senior living. If you’re concerned about healthcare in retirement, an excellent option is The Clare in downtown Chicago. The Clare offers continuing care options throughout retirement for any future healthcare concerns. By retiring at the Clare, you have confidence that you’ll receive the care you need so you can get back to experiencing the culture of downtown Chicago.