Sit on the Right side of the plane for the best views on flights from Chicago to Fort Myers. The right side wins overall because the Gulf Coast arrival into RSW on the right is genuinely spectacular — Sanibel, Estero Bay, and the Cape Coral canal grid are among the most visually distinctive features in Florida from the air. The Chicago departure view on the left is excellent but brief; the coastal arrival scenery on the right lasts longer and is more varied.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. ORD's most common southbound departures (runways 10L/10C heading east then turning south) put the left side facing the Chicago skyline and Lake Michigan shoreline. You get a clear view of the downtown Loop, Grant Park, and the lakefront as the aircraft banks south. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Grant Park and Museum Campus, Midway Airport to the south.

When landing at Southwest Florida International (RSW), sit on the Right side for the best views. RSW's primary approach is from the north or northeast on runway 06/24. A northeast approach puts the right side facing the Gulf of Mexico coastline, Estero Bay, and the barrier islands including Fort Myers Beach and Sanibel Island as you descend over the coastal flats. Notable sights include: Sanibel Island and Captiva Island, Estero Bay and Pine Island Sound, Fort Myers Beach barrier island, Cape Coral canal grid.

The flight from Chicago Ohare International (ORD) to Southwest Florida International (RSW) takes Approximately 2 hours 30 minutes to 2 hours 45 minutes.

The flight tracks southeast over Indiana farmland, then crosses Kentucky and Tennessee, passing west of the Appalachian foothills. Over Georgia and northern Florida the terrain flattens into pine forest and wetlands. The route crosses the Florida peninsula roughly over the Orlando area before descending toward the Gulf Coast, with the Everglades visible to the southeast in the final descent.