Sit on the Right side of the plane for the best views on flights from Tampa to Chicago. The right side wins overall because the Tampa Bay and Sunshine Skyway departure view is one of the most visually striking moments of the flight. The landing view of Chicago is excellent on the left, but the right side also gets reasonable views of the Chicago suburbs on approach, making it competitive throughout. The Tampa departure spectacle tips the balance to the right.

During takeoff from Tampa International (TPA), sit on the Right side for the best views. TPA typically departs on runway 19L/19R heading south before turning north, or departs runway 1L/1R heading north. On a northbound departure, the right side gives you Tampa Bay sprawling to the east and southeast, with the Sunshine Skyway Bridge clearly visible as a dominant structure crossing the bay mouth. Downtown Tampa's skyline also appears to the right as you climb out. Notable sights include: Tampa Bay, Sunshine Skyway Bridge, Downtown Tampa skyline, Hillsborough Bay.

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. On approach from the south, the left side faces east toward downtown Chicago, giving a clear view of the Lake Michigan shoreline and the Chicago skyline including the Loop. The lakefront parks and the distinctive grid of the city are easily readable from altitude. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Chicago River grid, Grant Park and lakefront.

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

The flight tracks north-northwest over central Florida's flat lake-dotted interior, then crosses Georgia and Tennessee before entering the Ohio Valley. Over Kentucky and Indiana the terrain is rolling agricultural land with the Ohio River visible as a broad winding boundary. The flight crosses the flat corn and soybean fields of central Indiana before descending into the Chicago metro area. No significant mountain ranges are crossed on this route.