Most people who end up in Oak Park didn’t plan on it. They were looking at places in Andersonville or Logan Square, started doing the math, and someone suggested they take the train out to see a house on Humphrey. They stood on the porch of a 1920s brick two-flat and something clicked.
It’s a common story. Oak Park has long pulled in Chicago buyers who hit a wall in the city, whether that’s budget, space, schools, or just a feeling that they want a yard without moving somewhere they’d never go to dinner. A lot of people right now are trying to figure out if 2026 is the year to actually do it.
The two markets are moving in fairly different directions, which makes that question more interesting than it used to be…