Sit on the Left side of the plane for the best views on flights from Montego Bay to Chicago. Left side wins both ends of the flight. At takeoff you get the Caribbean coastline and Montego Bay, and at landing you get the Chicago skyline and Lake Michigan. During the cruise over the Gulf of Mexico and central US, neither side has a decisive advantage, but the bookend views make left the clear choice for the full journey.

During takeoff from Sangster International (MBJ), sit on the Left side for the best views. MBJ's primary departure runway is 07, heading east, which puts the left (north) side facing the Caribbean Sea and the Jamaican coastline. You get a clear view of the turquoise waters of the Montego Bay marine park and the hotel strip along the coast as the aircraft climbs and turns northward. Notable sights include: Montego Bay harbor and coastline, Doctor's Cave Beach strip, the blue Caribbean waters to the north, the green limestone hills of the Cockpit Country to the south visible on the right.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. ORD typically lands on runways 10L/10C/10R heading east, or 28L/28C/28R heading west depending on winds. On the more common westerly approach (runway 28), the aircraft comes in from the east over the Chicago suburbs, and the left side faces south toward downtown Chicago's skyline, Lake Michigan's southern shoreline, and the dense urban grid of the city. This is the more dramatic and recognizable view. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock visible), southern Lake Michigan shoreline, the dense urban grid of Chicago's North Side, O'Hare's runway complex visible ahead.

The flight from Sangster International (MBJ) to Chicago Ohare International (ORD) takes Approximately 3 hours 30 minutes to 4 hours.

After departing Jamaica the route crosses the western Caribbean Sea, then the Yucatan Channel between Cuba and Mexico, followed by the Gulf of Mexico. Over the US the route crosses the Mississippi Delta region near the Louisiana-Mississippi coast, then tracks north over the Mississippi River valley through Tennessee and Kentucky, before crossing into Illinois and descending toward Chicago. The Mississippi River is the most visually distinctive landmark mid-flight, appearing as a wide silver ribbon cutting through flat agricultural land.