For almost 20 years, I have roamed the streets of Chicago and its suburbs for this magazine, checking out houses, schools, parks, stores, and other elements that contribute to quality of life. Along the way, I have found that in a metro area that stretches to the corners of six counties—and beyond—you can find an enormous variety of ways to live well.

Whether your conception of life lived well occurs in a super-tall high-rise at the pulsing center of a city, a tranquil little village with its sepia-toned charm intact, or something in between, you can find it in the Chicago area. In these pages, I will show you around 20 of my favorite places, including affluent areas filled with picturesque dream homes and more modestly priced places that are just as long on charm.

In my experience, these selected towns and neighborhoods distinguish themselves in several key ways. I looked at house prices, with an eye toward affordability in these complicated economic times. Ease of transportation—both public and by car—plays increasingly on time, expenses, and general comfort. Many parents make their residential decisions based on school quality, so I factored in that criterion using a variety of measures, including test scores and my own long experience in assessing schools for this magazine. (For example, see my report on the best public high schools in the October 2007 issue. In December 2007, senior editor Geoffrey Johnson filed a similar report for private high schools. We will be reporting on elementary schools in the October 2010 issue.) Finally, I hold that a lively town or neighborhood needs to be anchored by good shopping and dining choices that ideally join to form the social center of the community.

The selections I made—which follow in no particular order—range from a postcard-perfect town square nestled among streets of Victorian homes to an old-line Chicago neighborhood chock-a-block with bungalows and its own walkable restaurant strip. All of them are places with uncommon flavor.

You don’t merely buy or rent a home, you invest in a community as well, and in these 20 places, you get a lot in that deal. Come with me and take a look.