Sit on the Left side of the plane for the best views on flights from Georgetown to Chicago. Left side wins at both ends of the flight. Takeoff gives you Grand Cayman's most photogenic geography — Seven Mile Beach and North Sound — and landing delivers the Chicago skyline and Lake Michigan on approach. The left side is the clear choice for the full journey.

During takeoff from Owen Roberts International (GCM), sit on the Left side for the best views. Owen Roberts typically departs runway 08 (eastbound) or 26 (westbound). On a northbound routing to ORD, aircraft often depart runway 08 heading east then turn north, putting the left (north) side over the full extent of Grand Cayman's Seven Mile Beach and the shallow turquoise waters of the North Sound. The right side gets the open Caribbean to the south. Notable sights include: Seven Mile Beach (long white sand strip along the northwest coast), North Sound (vast shallow lagoon), George Town harbor and cruise ship anchorage, the reef line visible as a color change from turquoise to deep blue.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. Arriving at O'Hare from the south, aircraft typically approach on runways 10L/10R or 28L/28R depending on wind. On a southerly approach heading northwest, the left side faces south toward the Chicago skyline, Lake Michigan's southern shoreline, and the dense urban grid of the city. The right side looks northwest over suburban sprawl with far less visual interest. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock, Tribune Tower visible as a cluster), Lake Michigan's southern tip and shoreline, the dense urban street grid of Chicago's North Side, O'Hare's distinctive multi-runway complex visible just before touchdown.

The flight from Owen Roberts International (GCM) to Chicago Ohare International (ORD) takes Approximately 3 hours 30 minutes to 4 hours.

After leaving the Cayman Islands the route tracks north-northwest over the western Caribbean, crossing Cuba's western provinces near Havana, then the Straits of Florida into the Gulf of Mexico. The flight crosses the Gulf and makes landfall somewhere along the Louisiana or Mississippi Gulf Coast. From there it tracks north over the Mississippi River valley through Arkansas, Missouri, and Illinois. The Mississippi River itself may be visible as a wide meandering ribbon on clear days. The flat agricultural patchwork of the Midwest dominates the middle and later portions of the flight.