Sit on the Left side of the plane for the best views on flights from Key West to Chicago. The left seat delivers the best views at both ends of this flight — the Keys archipelago on departure and the Chicago skyline and Lake Michigan on approach. Over the mid-flight cruise at 35,000 feet above Florida and the Midwest, neither side has a dramatic advantage, but the left side tracks closer to the Gulf Coast and later the western shore of Lake Michigan, offering more geographic context throughout.

During takeoff from Key West International (EYW), sit on the Left side for the best views. Key West International's primary departure runway (Runway 9) heads east, putting the left (north) side over the Gulf of Mexico shallows and the right side over the Atlantic. However, Runway 27 departures heading west put the left side over the lower Keys chain stretching toward Key Largo, which is the more visually rewarding view. On either departure, the left seat captures the full arc of the Keys archipelago as the aircraft banks north toward the Florida mainland. Notable sights include: The Lower Keys chain (Stock Island, Boca Chica, Big Pine Key), the shallow turquoise waters of the Gulf of Mexico, the Seven Mile Bridge connecting Marathon to the lower Keys, Florida Bay's tidal flats.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare primarily uses runways oriented east-west (9L/27R, 10/28) and north-south (4R/22L, 14R/32L). On the most common westerly approach (Runway 10/28 family), the left side faces south over the Chicago metropolitan grid, giving a clear view of the downtown skyline, Lake Michigan's shoreline, and the urban fabric of the city. The right side on this approach faces north over suburban sprawl with fewer distinctive features. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock Center visible as a cluster), Lake Michigan's western shoreline, the grid of Chicago's street network, the Des Plaines River valley.

The flight from Key West International (EYW) to Chicago Ohare International (ORD) takes Approximately 3 hours 15 minutes to 3 hours 45 minutes.

After departing the Keys, the flight crosses the Florida Peninsula over the Everglades and Lake Okeechobee (visible as a large circular inland lake), then tracks north over central Florida and Georgia. Over Tennessee and Kentucky, the Cumberland Plateau's ridgelines are faintly visible. Crossing into the Midwest, the flat agricultural grid of Indiana and Illinois dominates, with the Wabash and Illinois River valleys occasionally breaking the pattern before the Chicago metro comes into view.