Sit on the Right side of the plane for the best views on flights from Houston to Chicago. While left gives the better Houston departure view, right wins overall because the Chicago arrival view of the lakefront and Loop skyline is one of the most dramatic urban approaches in the US. Over the flight path through Arkansas and Illinois, the right side also picks up the Mississippi River crossing near Memphis or St. Louis depending on routing, which is a genuinely striking geographic feature.

During takeoff from George Bush Intcntl Houston (IAH), sit on the Left side for the best views. IAH typically departs northbound on runways 26L/26R or 15L/15R. On a northbound departure climbing out, the left (west) side gives a clear view back over downtown Houston's skyline and the Ship Channel industrial complex. The right side faces east toward open suburban sprawl with little of interest. Notable sights include: Downtown Houston skyline, Houston Ship Channel and port facilities, Lake Houston to the northeast, Buffalo Bayou corridor.

When landing at Chicago Midway International (MDW), sit on the Right side for the best views. MDW sits on Chicago's southwest side and typically lands on runway 31C/31L heading northwest, or runway 13C heading southeast. On approach from the south, the right (north/east) side gives a sweeping view of the Chicago lakefront, Grant Park, and the downtown Loop skyline along Lake Michigan. The left side faces southwest toward flat suburban Cook County with little visual interest. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Grant Park and Museum Campus, Midway Airport runways visible below on final approach.

The flight from George Bush Intcntl Houston (IAH) to Chicago Midway International (MDW) takes Approximately 2 hours 15 minutes to 2 hours 30 minutes.

The flight tracks north-northeast over the Piney Woods of East Texas, crosses into Arkansas over the Ouachita lowlands, then traverses the flat Mississippi Alluvial Plain. The Mississippi River crossing is the most visually striking midpoint feature — wide, brown, and unmistakable with its oxbow lakes and agricultural floodplain. The route then crosses southern Illinois farmland before descending into Chicago.