The current home of former Smashing Pumpkins frontman Billy Corgan (and the former home of Bulls legend Michael Jordan, if he could just unload that ginormous mansion), Highland Park may seem out of reach to many. But the thickets of million-dollar spreads along zigzagging ravines are interspersed with much smaller, cheaper colonials and Georgians.
Frank Lloyd Wright and his protégés saw fit to build here; the master architect’s Adams and Millard Houses lie along Lake Street. For the most affordable single-family houses, check out the Highlands district, says Coldwell Banker broker Pam Devendorf: “Homes run 2,000 to 3,200 square feet and sell for $350,000 to $600,000.”
Highland Parkers are blessed with easy access to Lake Michigan, to dozens of restaurants, beauty salons, and stores (including Anthropologie and Williams-Sonoma), and to the county’s best high school, Deerfield. Not to mention the suburb’s crowning glory: Ravinia, the former artists’ colony that has served as the summer home of the Chicago Symphony Orchestra for the past 77 years.