Sit on the Left side of the plane for the best views on flights from Chicago to Key West. Left side wins at both ends of the flight. During the cruise portion heading south-southeast, the left side also faces east, giving views of Florida's Gulf Coast cities like Tampa and Sarasota as the flight descends toward the Keys, while the right side looks out over the Gulf of Mexico. Left is the clear choice for the full journey.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare's most common departure runways (9L/9R heading east, or 10L/10R) put the left side facing north toward downtown Chicago. As the aircraft climbs and turns southward, the left side gets a clear view of the Chicago skyline, Lake Michigan's southern shoreline, and the dense urban grid of the city. Right side faces suburban sprawl with little of note. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), Lake Michigan southern shoreline, Chicago River corridor, Grant Park lakefront.

When landing at Key West International (EYW), sit on the Left side for the best views. Key West International sits on the eastern end of the island, and aircraft typically approach from the northeast on runway 09 heading west. On final approach, the left side faces south over the Atlantic and looks across the full length of Key West island, the historic Old Town district, and the surrounding turquoise shallow-water flats. The right side faces north toward Stock Island and the Gulf of Mexico. Notable sights include: Key West Old Town historic district, Duval Street corridor, Fort Zachary Taylor, surrounding turquoise Atlantic and Gulf shallow flats.

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

The flight tracks southeast over Indiana and Kentucky, then crosses Tennessee and Georgia before entering Florida near Gainesville. Over central Florida the route passes east of Tampa Bay, with the Gulf Coast visible to the right and the Atlantic coast to the left. Approaching South Florida, the Everglades appear as a vast flat mosaic of sawgrass marsh and water below. The Florida Keys then extend southwest as a thin chain of islands connected by the Overseas Highway, visible in the final descent.