Woodlawn

Woodlawn sits directly south of the Midway and is the neighborhood most changed by what's coming: the Obama Presidential Center rising in Jackson Park on its eastern edge. Investment is following, from new mixed-income developments along 63rd Street to the University of Chicago's steady southward expansion. The bones were always here: broad streets, brick flats, and the lakefront a walk away.

Transit is strong for the South Side: the Green Line's Cottage Grove terminal, the Metra Electric at 63rd, and the lakefront buses. Downtown is 20 minutes. Prices are climbing from a low base, which is exactly the window. Woodlawn suits buyers and renters who want to be near the Obama Center, the lake, and the university before the market finishes repricing all three.

Woodlawn offers strong transit access: a car is optional for many trips. One car typically covers the gap that transit leaves.

With a Walk Score of 75, Woodlawn is "Very Walkable": most errands can be accomplished on foot.

At roughly $12,000/year for 1 car, transportation is a moderate line item in Woodlawn's true cost. The neighborhood is served by the Green line.