Sit on the Left side of the plane for the best views on flights from Jacksonville to Chicago. Left side wins both ends of the flight. During the cruise over Georgia, Tennessee, and Kentucky, the left side also offers slightly better angles on the Cumberland Plateau terrain and the Ohio River crossing. It is the clear choice for the full journey.

During takeoff from Jacksonville International (JAX), sit on the Left side for the best views. JAX typically departs northwest on runway 7/25 or north on runway 14/32. A left-side seat during a northwesterly departure gives you a clear look back over the St. Johns River as it winds through Jacksonville and out toward the Atlantic. You'll also catch the sprawl of downtown Jacksonville and the river's distinctive S-curves before climbing out over Georgia. Notable sights include: St. Johns River and its S-curves through Jacksonville, downtown Jacksonville skyline, Jacksonville Beach coastline to the east, Blount Island marine terminal.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare predominantly uses runways oriented east-west and northwest-southeast. Arriving from the southeast, a left-side seat gives you the best view of Lake Michigan's southern shoreline, the Chicago downtown skyline, and the dense urban grid of the city as you descend over the western suburbs. The right side faces away from the lake toward flat exurban terrain. Notable sights include: Lake Michigan southern shoreline, Chicago downtown skyline including Willis Tower, the dense urban grid of Chicago's North Side, O'Hare's distinctive runway complex visible on final approach.

The flight from Jacksonville International (JAX) to Chicago Ohare International (ORD) takes Approximately 2 hours 30 minutes to 2 hours 50 minutes.

The flight tracks northwest over Georgia's coastal plain, crosses the Appalachian foothills near Atlanta, passes over the Cumberland Plateau in Tennessee, crosses the Ohio River near Louisville or Evansville, then traverses the flat agricultural plains of central Indiana and Illinois before descending into Chicago. The Ohio River crossing is the most visually distinctive midpoint feature, a wide silver ribbon cutting through forested bottomland.