The Tampa Bay departure offers a more sustained and clearer scenic sequence than the brief skyline glimpse on arrival, and the cruise portion over Georgia, Tennessee, and Kentucky is largely flat with little to distinguish either side.
Flown TPA to MDW? Did we get it right?
Flight Path
Tampa to Chicago is 998 miles (1,607 km), a flight of about 2 hours 20 minutes.
Rolling terrain of northern Georgia and Tennessee, the Cumberland Plateau foothills, and the flat agricultural plains of southern Illinois as the route approaches Chicago.
Great circle distance and headings ›Phase by phase

Takeoff from TPA
LEFTDeparting TPA northbound, the aircraft banks over Tampa Bay before settling on course toward Chicago, giving left-side passengers a clear view of the bay, the Courtney Campbell Causeway, and the Pinellas peninsula shoreline. The right side mostly shows flat inland Florida suburbs.

Landing at MDW
RIGHTOn approach into MDW from the southwest, the flight path passes close enough to Chicago's southwest side that the downtown skyline and a sliver of Lake Michigan become visible on the right side of the aircraft just before landing. The left side shows flat suburban grids with little variation.
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About This Route
Which side of the plane should I sit on flying from Tampa International (TPA) to Chicago Midway International (MDW)?
Sit on the Left side of the plane for the best views on flights from Tampa to Chicago. The Tampa Bay departure offers a more sustained and clearer scenic sequence than the brief skyline glimpse on arrival, and the cruise portion over Georgia, Tennessee, and Kentucky is largely flat with little to distinguish either side.
What can I see during takeoff from Tampa International in Tampa?
During takeoff from Tampa International (TPA), sit on the Left side for the best views. Departing TPA northbound, the aircraft banks over Tampa Bay before settling on course toward Chicago, giving left-side passengers a clear view of the bay, the Courtney Campbell Causeway, and the Pinellas peninsula shoreline. The right side mostly shows flat inland Florida suburbs. Notable sights include: Tampa Bay, Davis Islands, Courtney Campbell Causeway, Pinellas peninsula coastline.
What can I see when landing at Chicago Midway International in Chicago?
When landing at Chicago Midway International (MDW), sit on the Right side for the best views. On approach into MDW from the southwest, the flight path passes close enough to Chicago's southwest side that the downtown skyline and a sliver of Lake Michigan become visible on the right side of the aircraft just before landing. The left side shows flat suburban grids with little variation. Notable sights include: Chicago skyline (Willis Tower, Sears/Willis area), Lake Michigan shoreline, Midway's surrounding grid neighborhoods.
How long is the flight from Tampa to Chicago?
The flight from Tampa International (TPA) to Chicago Midway International (MDW) takes about 2 hours 20 minutes. The shortest flight path between them is 998 miles (1,607 km); winds and air traffic control usually add a few percent.
What does the Tampa to Chicago flight path pass over?
Rolling terrain of northern Georgia and Tennessee, the Cumberland Plateau foothills, and the flat agricultural plains of southern Illinois as the route approaches Chicago.