Sit on the Right side of the plane for the best views on flights from Chicago to Indianapolis. Right-side seats dominate both segments: Chicago's lakefront and skyline on departure, and Indianapolis's downtown and White River valley on arrival. The route itself trends slightly south-southwest, so right-side passengers see the most distinctive urban and water features throughout.

During takeoff from Chicago Midway International (MDW), sit on the Right side for the best views. Right-side seats capture the Chicago skyline and Lake Michigan as you climb out. Midway typically departs runways 31L/31R or 22L/22R; either direction gives right-side passengers a view of downtown Chicago's high-rises and the lake's shoreline during the initial climb. Notable sights include: Lake Michigan (immediate east), Chicago downtown skyline (northeast), Bridgeport neighborhood industrial area (north), Des Plaines River valley (west).

When landing at Indianapolis International (IND), sit on the Right side for the best views. Right-side seats offer the best approach view into Indianapolis. Typical landing runways are 31L/31R or 05L/05R; a right-hand approach to either runway gives right-seat passengers a clear view of downtown Indianapolis and the White River valley as you descend. Notable sights include: White River (prominent serpentine feature), downtown Indianapolis skyline (modest but visible), Fountain Square district, suburban sprawl to the south and west.

The flight from Chicago Midway International (MDW) to Indianapolis International (IND) takes Approximately 1 hour 15 minutes.

The flight path crosses central Illinois farmland and scattered small towns. Around the midpoint (near Champaign-Urbana area, roughly 40 miles south-southwest of Chicago), you'll see flat agricultural terrain with geometric field patterns, sparse tree lines, and occasional small lakes. The Kankakee River valley may be visible to the south. No significant mountains or dramatic topography—this entire route is across the glaciated Midwest plain with elevations between 600–800 feet. The landscape remains predominantly rural and agricultural until the approach to Indianapolis.