Sit on the Left side of the plane for the best views on flights from Orlando to Chicago. Left side wins both ends of the flight. During the cruise northward over the Midwest, the left side also faces west, giving views over the flat agricultural plains of Tennessee, Kentucky, and Indiana — less dramatic than coastal routes but consistent. Right side offers little advantage at any phase.

During takeoff from Executive (ORL), sit on the Left side for the best views. ORL typically departs runway 7 heading east, then turns northbound. A left (north-facing) seat captures the Orlando metro sprawl, the chain of lakes through the city, and Lake Apopka to the northwest as the aircraft climbs and banks north. Notable sights include: Lake Apopka (large lake northwest of Orlando), Orlando's downtown lake chain (Lakes Eola, Ivanhoe, Virginia), Walt Disney World resort complex to the southwest, and the broad flatlands of the Wekiva River basin.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. ORD predominantly uses runways 10L/10C/10R for eastward arrivals or 27L/27R for westward approaches. On a southbound arrival from the north or northwest, the left side faces south and east toward the Chicago skyline, Lake Michigan's southern shoreline, and the dense urban grid of the North Side neighborhoods. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock visible as distinct towers), southern Lake Michigan shoreline, the dense street grid of Chicago's North Side, and the Des Plaines River valley near O'Hare.

The flight from Executive (ORL) to Chicago Ohare International (ORD) takes Approximately 2 hours 15 minutes to 2 hours 30 minutes.

The flight tracks north-northwest over Georgia and Tennessee, crossing the Cumberland Plateau (a low, flat-topped upland visible as a textured ridge system), then over Kentucky's Bluegrass region and the Ohio River valley — a wide, winding river visible as a silver ribbon marking the Kentucky-Indiana border — before crossing the flat agricultural grid of central Indiana and Illinois en route to Chicago