Sit on the Right side of the plane for the best views on flights from Chicago to Montego Bay. The right side wins overall due to the spectacular Chicago departure view — the skyline and Lake Michigan together make for one of the best urban departures in North America. The landing advantage on the left is real but the approach view is relatively brief. Right side also tracks closer to the Gulf of Mexico coastline mid-flight.

During takeoff from Chicago Ohare International (ORD), sit on the Right side for the best views. O'Hare's primary departure runways (9L/9R eastbound or 10L/10R) send aircraft climbing southeast over the Chicago metro. The right side gives you the downtown Chicago skyline and Lake Michigan shoreline as you gain altitude. Left side faces northwest toward suburban sprawl with little of interest. Notable sights include: Downtown Chicago skyline (Willis Tower, John Hancock), Lake Michigan shoreline, Chicago River corridor, Grant Park and Museum Campus.

When landing at Sangster International (MBJ), sit on the Left side for the best views. Sangster International's primary runway (07/25) has aircraft typically approaching from the west over the Caribbean Sea, landing eastbound on runway 07. On left side you get the Blue Mountains of Jamaica on the horizon and the lush green Jamaican coastline. Right side faces north over open water. Notable sights include: Montego Bay harbor and city waterfront, Doctor's Cave Beach area, the Blue Mountains visible to the east, lush green limestone karst hills of St. James parish.

The flight from Chicago Ohare International (ORD) to Sangster International (MBJ) takes Approximately 3 hours 45 minutes to 4 hours 15 minutes.

The flight tracks southeast from Chicago over Indiana and Kentucky, then across Tennessee and Georgia before crossing the Florida peninsula near Orlando. You cross the Florida Straits — the narrow stretch of water between Florida and Cuba — at cruise altitude where Cuba's northern coast is faintly visible on clear days. The route then crosses the open Caribbean Sea before the Jamaican north coast comes into view. The Mississippi River is visible early in the flight, and the Gulf of Mexico coastline of Florida is visible from the right side during the Florida crossing.