Sit on the Left side of the plane for the best views on flights from New Orleans to Chicago. The left side wins both the departure over Lake Pontchartrain and the arrival over Chicago's skyline and Lake Michigan. During the cruise portion heading north-northeast, the left side also keeps you oriented toward the Mississippi River valley as it passes to the west over Tennessee and Kentucky.

During takeoff from Louis Armstrong New Orleans International (MSY), sit on the Left side for the best views. MSY typically departs east on runway 10R/10L, so the left (north) side gives you a clear view back over Lake Pontchartrain as you climb out. The lake's massive expanse and the causeway bridge stretching across it are unmistakable from altitude. Notable sights include: Lake Pontchartrain, Lake Pontchartrain Causeway, the Mississippi River bend through New Orleans, the French Quarter grid pattern.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. ORD predominantly lands from the east on runways 10L/10C/10R, meaning the aircraft approaches from over the western Chicago suburbs heading west. The left (south) side gives you the best view of the Chicago skyline, Lake Michigan shoreline, and the dense urban grid of the city proper as you descend. Notable sights include: Chicago downtown skyline, Lake Michigan shoreline, the Chicago River, the dense urban grid of the South Side.

The flight from Louis Armstrong New Orleans International (MSY) to Chicago Ohare International (ORD) takes Approximately 2 hours 15 minutes to 2 hours 30 minutes.

The flight tracks north-northeast over central Mississippi and Tennessee, crossing the Tennessee River system and the rolling terrain of western Tennessee. Over Kentucky and southern Illinois the land flattens into the Ohio River valley, with the Ohio River itself potentially visible as a wide brown ribbon. The route then crosses the flat agricultural plains of central Illinois before descending into Chicago.