Hello David. Well after the winter you folks have had in Chicago, I'd say ANYWHERE in the Charleston area is desirable! I'm a Kentucky transplant - moved to the area just a few months before the devastation of Hurricane Hugo, leaving Kentucky after a record winter of blizzards and a spring of floods!
David, the answer to your question needs to be qualified by your budget, and by your personal preferences. Charleston has a plethora of beautiful island communities such as Kiawah, Seabrook, Sullivan's Island, and more. Downtown Charleston is treasure-trove of historical homes, well-maintained and a very traditional Southern lifestyle. We also have a couple of premier retirement communities in the Elms and Cane Bay - a Del Webb community. And then, of course, there's the Summerville area with it's annual Flowertown Festival and all the charm of a small town "Hometown USA" feel. Then there's the unique charm of the front porches and sidewalks and "Family Circle Cup" of Daniel Island. Rural West Ashley is great for nature enthusiasts, with the ACE Basin and the Edisto.
Davud - there's much to love about many of the areas in Charleston, and I'd be hard pressed to select only a couple. Decide upon a budget, set your lifestyle priorities, and you'll find a neighborhood in the Charleston area that's a perfect match. Contact me, and I'll be glad to send you some links with information about the environmental, historical, and cultural activities and events in the area, to help you decide where you'd like to live.
Come on down! the weather's great!