Chicago : Illinois


What It Is Like to Retire in Chicago

Living in Chicago as a retirement community has many advantages for active adults 55+ with the means to do it. You get a walkable downtown with great public transportation. Many apartments overlook beaches or harbors on Lake Michigan. Great boating is at your doorstep, as are many lifetimes worth of cultural programs. With 18 miles of public parks around the lake you get stunning views of the Lake. For serious bikers, the Grand Illinois Trail is a 537-mile bike loop trail to the banks of the Mississippi and back. The metro area (10.0 million people) includes parts of Illinois, Indiana and Wisconsin.

Opportunities of every description for paid work or volunteering are all around you. And you hardly ever need to drive anywhere. Chicago (population in 2020 over 2.7 million), draws in retirees from suburbs and all over the mid-west because it such a manageable, picturesque, and bustling community. For a major city, it retains a mid-western friendliness, even on the dazzling commercial center of Michigan Avenue. Photo of Chicago River by Jeff Russell.

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Here is Topretirements Mini-Retirement Guide to Illinois


Where to Retire in Chicago and Home Prices

There are many neighborhoods to live in. The North Side has long been gentrified and tends to be the most expensive and charming. High rises along the lake provide wonderful views. The area around the city is home to many new and existing 55+ and active adult communities, many of which have extensive amenities.
Some high-rises in the city are attracting empty nesters.  Prices of condos go from the $300's to  $1 million or more.  According to the National Association of Realtors, the average selling price in the greater Chicago area (including Napier and Elgin) was $318,100 in the 4th quarter of 2021.


What Is Special about Chicago

A major city that remains manageable; Great parks and views of Lake Michigan; Michigan Avenue shopping;  Neighborhoods; Sports teams;  Chicago Art Institute. And the Chicago Cubs and Wrigley Field, of course!


What Is Not Special about Chicago

• Have to be ready for an urban environment • It might be hard to make new friends • It is expensive • Really cold winters

Who Will Like Retirement in Chicago

As a retirement community adults like living here because it is one of the world's great cities in a beautiful natural setting. There is a strong economic base with ample opportunities for work and volunteer. There is always something to do.


Local Economy Is Driven by

Big business, Tourism, Services, Retail


Climate and Physical Environment

Chicago is located on the southwestern edge of Lake Michigan. Several rivers flow through here, including the Chicago River. From this port a ship can get to any harbor in the world. Winters are cold and summers are beautiful.

Restaurants & Cultural Scene

Chicago has a cultural scene that befits one of the world’s great cities. Its museums, including the Art Institute of Chicago are first rate. The Chicago Theatre presents a continuing schedule of plays and musicals. The Lyric Opera of Chicago, the Chicago Symphony Orchestra, the Joffrey Ballet, and several modern and jazz dance troupes are just a small sampling of the cultural resources here. There is an endless choice of restaurants from ethnic to the very fancy.


Like any big city, Chicago has its share of crime. Obviously neighborhood has a lot to do with that.  The crime rate is about double the national average.

Medical Facilities

There is an array of major hospitals.


OHare Airport is one of the busiest airports in the world. Southwest Airlines operates out of the more conveniently located Midway. Amtrak has a major station here, and the El and buses provides excellent public transportation around town.


Valuable Links

City of Chicago


What people are saying about Chicago

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