Sit on the Right side of the plane for the best views on flights from New Orleans to Chicago. Right-side seats win overall because the takeoff views of the Mississippi River and Lake Pontchartrain are more visually distinctive and geographically dramatic than the landing views. While left-side landing views are solid, the northern route's river geography is the flight's most memorable feature.

During takeoff from Louis Armstrong New Orleans International (MSY), sit on the Right side for the best views. Right-side seats capture the Mississippi River's dramatic meanders and Lake Pontchartrain as the aircraft climbs northward. MSY typically departs to the north or northeast, and right-side views show the river's distinctive curves and the lake's expanse stretching toward the horizon. Notable sights include: Mississippi River (multiple oxbow bends), Lake Pontchartrain, New Orleans urban grid, Cypress swamps to the east.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. Left-side seats offer the best views during approach to MDW. Chicago's downtown skyline and Lake Michigan are positioned on the left as aircraft descend from the northeast or east. The contrast between the urban core and the lake's expanse makes for striking visuals during final approach. Notable sights include: Lake Michigan (western shoreline), Chicago downtown skyline, Illinois prairie to the west, Midway's runway complex.

The flight from Louis Armstrong New Orleans International (MSY) to Chicago Midway International (MDW) takes Approximately 3 hours 15 minutes.

The flight path crosses central Illinois, passing east of St. Louis (visible as a distant urban cluster on the horizon if flying at cruise altitude around 30,000 feet). The Illinois River and its valley are visible during the middle portion of the flight. The terrain transitions from Mississippi Delta wetlands to the relatively flat agricultural plains of Illinois and Indiana, with scattered lakes and reservoirs becoming visible as the aircraft approaches the Chicago area. The Ohio River valley lies to the east of the direct route but may be visible on clear days from cruise altitude.