✈️ The 5 Chicago Neighborhoods Where Buyers Are Winning Right Now By Trevor Hughes | Paper Plane Realty | May 2026 Let's be honest — the Chicagoland market right now can feel like a turbulent flight. In some neighborhoods, buyers are getting tossed around in bidding war after bidding war, overpaying just to land somewhere. In others? The runway is clear, conditions are favorable, and smart buyers are closing with room to breathe. At Paper Plane Realty, we track this market ev