Sit on the Right side of the plane for the best views on flights from Chicago to Mexico City. The right side wins overall due to the spectacular Popocatépetl and Iztaccíhuatl approach on landing, which is one of the most dramatic volcanic views available on any commercial route. The takeoff views from either side are relatively similar — flat Midwest terrain — so the landing experience tips the balance decisively to the right.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare's primary departure runways (9L/9R heading east, or 10L/10R) send aircraft climbing over the western Chicago suburbs before turning south. A left/south-facing seat gives you the Chicago skyline in the distance as you climb out, with Lake Michigan visible to the east. Departures heading southwest on runways 28L/28R put the city and lake on the left side during the initial climb. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), southern Lake Michigan shoreline, Illinois flatlands grid pattern, Chicago's dense suburban street grid.

When landing at Licenciado Benito Juarez International (MEX), sit on the Right side for the best views. Mexico City's airport sits on the eastern side of the city, and aircraft typically approach from the northeast or east on runway 05R/05L heading southwest. A right-side seat on approach gives you the snow-capped volcanoes Popocatépetl and Iztaccíhuatl to the southeast, which are among the most dramatic visible landmarks on any approach in the Americas. Left side faces the city center and mountains to the west. Notable sights include: Popocatépetl volcano (active, 17,802 ft), Iztaccíhuatl volcano (17,159 ft), Valley of Mexico urban sprawl, Sierra Nevada mountain range flanking the valley.

The flight from Chicago Ohare International (ORD) to Licenciado Benito Juarez International (MEX) takes Approximately 3 hours 45 minutes to 4 hours 15 minutes.

The route tracks southwest over central Illinois farmland, then crosses the Mississippi River near St. Louis, continues over the Ozark Plateau in Missouri and Arkansas, crosses the Rio Grande into Mexico near Laredo or Monterrey, then passes over the Sierra Madre Oriental before descending into the high-altitude Valley of Mexico. The Sierra Madre Oriental ridgelines are visible from both sides over northeastern Mexico, and the transition from the dry scrubland of northern Mexico to the greener central highlands is noticeable around Monterrey.