Sit on the Left side of the plane for the best views on flights from Chicago to San Jose Del Cabo. Left-side seats win overall because the approach into Midway offers more sustained visual interest than the departure. While the takeoff over Lake Michigan is brief, the landing descent provides extended views of the Chicago shoreline, industrial corridor, and the airport itself. The outbound flight over the Gulf of Mexico offers little distinctive geography for either side.

During takeoff from Chicago Midway International (MDW), sit on the Right side for the best views. Right-side seats capture the initial climb-out over Lake Michigan and the Chicago shoreline. Midway typically departs runways 4L/4R or 13L/13R; runway 4 departures head northeast over the lake, giving right-seat passengers a direct view of the water and downtown Chicago skyline receding behind. Notable sights include: Lake Michigan (immediate right, extending to horizon), Chicago downtown skyline (left-rear, receding), Calumet River industrial area (below, left side), Indiana shoreline (right-rear, distant).

When landing at Los Cabos International (SJD), sit on the Left side for the best views. Left-seat passengers get the best approach view into Midway. Typical landing runways are 4L/4R or 13L/13R; runway 4 approaches from the northeast over Lake Michigan, and left-side seats face the water and Chicago's south lakefront during descent. The approach path offers extended views of the shoreline and the city's southwest neighborhoods. Notable sights include: Lake Michigan (left side, extending to horizon during approach), Chicago shoreline and beaches (left-center, growing larger), Calumet River and industrial corridor (left-forward, below), Midway Airport grounds (forward, final approach).

The flight from Chicago Midway International (MDW) to Los Cabos International (SJD) takes Approximately 4 hours 15 minutes.

After climbing out over Lake Michigan and crossing Illinois, the flight path heads south-southwest over Missouri (Mississippi River visible near St. Louis area if at lower cruise altitudes), then continues over Arkansas and into the Gulf of Mexico. The Gulf crossing occupies roughly 2 hours of flight time with minimal landmarks—open water and occasional weather systems. As the aircraft approaches the Baja California Peninsula, the Sierra de la Laguna mountain range becomes visible on the left (east) side during descent, appearing as a north-south trending ridge. The peninsula's arid terrain and sparse vegetation become increasingly apparent in the final 30 minutes of flight.