Sit on the Left side of the plane for the best views on flights from Indianapolis to Chicago. Left side wins overall because the landing view—Lake Michigan, downtown Chicago skyline, and the South Side approach—is more visually distinctive than the takeoff view. The landing sequence offers more dramatic geography.

During takeoff from Indianapolis International (IND), sit on the Right side for the best views. Right-side seats capture the White River winding through downtown Indianapolis during initial climb. The river's distinctive curves and the downtown skyline provide clear visual reference as you depart northwestbound. Notable sights include: White River (downtown Indianapolis), Indianapolis Motor Speedway (visible 5 miles west), downtown Indianapolis skyline, suburban sprawl extending north toward Carmel.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. Left-side seats offer the best view during approach to Midway's runways (typically 31L/31R or 22L/22R depending on wind). You'll see the Chicago skyline, Lake Michigan, and the South Side neighborhoods that define the approach corridor. Notable sights include: Lake Michigan (eastern horizon), Chicago downtown skyline, Midway's runways and taxiway system, South Side residential neighborhoods (Ashburn, Evergreen Park).

The flight from Indianapolis International (IND) to Chicago Midway International (MDW) takes Approximately 45 minutes.

The flight path crosses central Indiana farmland and the Kankakee River valley. Around the midpoint (near Kentland, Indiana), you'll pass over flat agricultural terrain with scattered towns. As you approach Illinois, the landscape remains predominantly rural with occasional small towns. The Kankakee River is visible as a meandering waterway in the southern portion of the approach corridor. No major mountain ranges or dramatic terrain features exist along this route—the entire corridor is characterized by flat to gently rolling Midwestern farmland and prairie.