Sit on the Left side of the plane for the best views on flights from Houston to Chicago. Left side wins at both ends of the flight. Houston's skyline and Ship Channel on departure, and the Chicago Loop with Lake Michigan on approach, are both on the left. The mid-flight view over flat Arkansas and Illinois farmland is similar on both sides, so the landmark advantage is decisively left.

During takeoff from William P Hobby (HOU), sit on the Left side for the best views. Hobby Airport's most common departure is runway 04 (northeast), which puts the left side facing northwest toward downtown Houston. You get a clear view of the Houston skyline, the Ship Channel, and the sprawling urban grid as you climb out. Right side faces southeast toward open suburban sprawl and Galveston Bay's far edge. Notable sights include: Downtown Houston skyline, Houston Ship Channel, Galveston Bay (distant, southeast), Buffalo Bayou corridor.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare's primary arrival runways from the south typically bring aircraft in on headings around 270-280 (westward) or 320 (northwest), and on final approach from the south the left side faces south and east toward downtown Chicago and Lake Michigan. The Chicago skyline and the lakefront are clearly visible on the left during descent. Right side faces west into flat suburban sprawl. Notable sights include: Chicago downtown skyline (Loop), Lake Michigan shoreline, Grant Park and Museum Campus, O'Hare suburban grid of Schaumburg and Rosemont.

The flight from William P Hobby (HOU) to Chicago Ohare International (ORD) takes Approximately 2 hours 30 minutes.

The flight tracks northeast over the flat Gulf Coastal Plain of east Texas, then crosses the Arkansas River valley near Little Rock, followed by the flat agricultural plains of central Arkansas and Missouri. The Mississippi River is a notable crossing point roughly 90 minutes in, visible as a wide brown meandering river near Memphis or the Missouri bootheel. Northern Illinois farmland dominates the final 45 minutes before Chicago's suburban sprawl appears.