Sit on the Left side of the plane for the best views on flights from Los Angeles to Chicago. The left side wins overall because the Chicago arrival view — the lakefront, the Loop skyline, and Lake Michigan all at once on approach — is one of the most dramatic urban arrival scenes in US aviation. The takeoff advantage slightly favors right, but the landing view on the left is the highlight of this route.

During takeoff from Los Angeles International (LAX), sit on the Right side for the best views. LAX departures heading east typically use runways 24L/24R departing westward over the ocean before turning, or runways 06L/06R heading east. On the dominant westward departure (runway 24s), right-side passengers get the Santa Monica Bay and Palos Verdes Peninsula before the turn inland. On eastward departures (runway 06s), right side captures the Hollywood Hills, Griffith Observatory area, and the San Gabriel Mountains as the aircraft climbs northeast toward the route. Notable sights include: Santa Monica Bay coastline, Palos Verdes Peninsula, San Gabriel Mountains, downtown Los Angeles grid.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. Midway typically uses runways 31C/31L for arrivals from the southwest, meaning the aircraft approaches from the south-southwest. Left-side passengers get a clear view of the Chicago lakefront, Grant Park, the Loop skyline, and Lake Michigan as the aircraft descends over the South Side neighborhoods. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Grant Park and Museum Campus, South Side street grid.

The flight from Los Angeles International (LAX) to Chicago Midway International (MDW) takes Approximately 3 hours 30 minutes to 4 hours.

After clearing the San Gabriel and San Bernardino Mountains, the route crosses the Mojave Desert, then the Colorado River into Arizona. Over New Mexico and the Texas Panhandle the terrain is flat high plains. Kansas and Missouri bring the flat agricultural patchwork of the Great Plains — enormous circular center-pivot irrigation fields are visible from cruise altitude. The Mississippi River crossing near St. Louis is a notable landmark before the final descent into Chicago.