There is a nice triangle of lower cost areas in the Midwest, bordered by Columbus, OH, Louisville, KY, and Indianapolis, IN (Cincinnati included in the triangle). All three are large enough cities for your cultural needs, with many smaller towns nearby (Lexington, KY, Bloomington, IN, Dayton, OH. Lots of good sized airports to choose from. Winters in mid-Indiana/Ohio may be a little stiffer, but not as bad as Michigan, Chicago and WI.
The Ohio/IN area has not fully recovered from the housing crisis and offers some of the lowest cost housing in the country-some of these areas constantly appear on "lowest cost retirement cities" in USA. Colts, Pacers and Indianapolis Indians (AAA baseball) in Indy, while Cincinatti is home to the Reds, and Bengals. Many NCAA schools in the area include Ohio State and Indiana U.
Most of these areas have suburbs that are walking friendly (Ohio is crisscrossed with great paved bike paths) and feel like small towns used to feel.
Low crime, low taxes. Lots to like if you can handle some cold weather and a little snow.