Sit on the Left side of the plane for the best views on flights from Chicago to Indianapolis. The left side delivers the Chicago lakefront and skyline spectacle on departure, which is the visual highlight of this short flight. The right side wins at landing but the Indy approach is less dramatic. Left overall for the Chicago views.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. Departing O'Hare typically heads east or southeast toward Indiana. The left (north/east) side gives you a clear view back over Chicago's dense urban grid, the lakefront, and downtown skyline as you climb out. The right side faces suburban sprawl with little of interest. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), Lake Michigan shoreline, Chicago River corridor, O'Hare's own massive runway complex receding below.

When landing at Indianapolis International (IND), sit on the Right side for the best views. Indianapolis International sits southwest of downtown Indy. On approach from the northwest, the right side faces northeast toward downtown Indianapolis, giving a clear view of the city center and the White River corridor. The left side looks out over flat farmland with little to distinguish it. Notable sights include: Downtown Indianapolis skyline, White River, Indianapolis Motor Speedway (visible as a large oval track northwest of downtown), suburban Indianapolis grid.

The flight from Chicago Ohare International (ORD) to Indianapolis International (IND) takes Approximately 45-55 minutes.

The flight crosses flat glaciated agricultural land the entire way — northwestern Indiana's Kankakee River valley, the Calumet industrial corridor near the state line, and then central Indiana's perfectly gridded farmland. No significant terrain changes; elevation barely varies from around 600-800 feet above sea level throughout. The Wabash River and its tributaries may be visible as faint dark lines across the fields.