Sit on the Left side of the plane for the best views on flights from Fort Myers to Chicago. Left side wins at both ends of the flight. Over Fort Myers you get the river and harbor system on departure, and on arrival into ORD the left side delivers the full Chicago skyline and Lake Michigan shoreline — the most visually rewarding view of the entire route.

During takeoff from Southwest Florida International (RSW), sit on the Left side for the best views. RSW typically departs on runway 06 (heading northeast) or runway 24 (heading southwest). On a northbound flight to ORD, expect runway 06 departure. Left side gives you views over Fort Myers city, the Caloosahatchee River, and Charlotte Harbor as the aircraft climbs and turns north. Right side faces the Gulf of Mexico but the turn away from it happens quickly. Notable sights include: Caloosahatchee River winding east-west below Fort Myers, Charlotte Harbor estuary to the north, Cape Coral canal grid visible as a geometric pattern, Pine Island Sound barrier islands.

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 wind. On approach from the south, left side gives a clear view of downtown Chicago's skyline, Lake Michigan's shoreline, and the urban grid of the South and West sides. Right side faces suburban sprawl with fewer distinctive features. Notable sights include: Downtown Chicago skyline with Willis Tower and John Hancock Center, Lake Michigan shoreline and lakefront parks, Chicago River corridor, O'Hare airport approach over suburban Cook County grid.

The flight from Southwest Florida International (RSW) to Chicago Ohare International (ORD) takes Approximately 2 hours 45 minutes to 3 hours.

The flight tracks north-northwest over central Florida, crossing the Florida Panhandle or central Georgia depending on routing, then over Tennessee and Kentucky. Over Tennessee you may see the Cumberland Plateau's ridgeline terrain. Crossing into Indiana the landscape flattens into the agricultural grid of the Midwest — large rectangular fields of corn and soy visible from cruise altitude. The Wabash River and Kankakee River are occasionally identifiable as dark meandering lines through the flat terrain before Chicago suburbs appear.