While the left side wins a quick Chicago skyline glimpse at takeoff, the right side offers more sustained interest: distant Appalachian foothill terrain in cruise near Tennessee and Georgia, followed by a genuinely distinctive approach over Orlando's lakes and theme park landscape.
Flown MDW to MCO? Did we get it right?
Flight Path
Chicago to Orlando is 991 miles (1,595 km), a flight of about 2 hours 20 minutes.
The route crosses the Ohio River valley, the rolling hills of central Tennessee, and the northern edge of Georgia's Piedmont before descending into flat central Florida.
Great circle distance and headings ›
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Phase by phase
Takeoff from MDW
LEFTDeparting Midway to the southeast, the left side offers a brief but clear view back toward the Chicago skyline and the edge of Lake Michigan before the aircraft turns onto its southbound track. The right side only shows flat suburban grid streets.
Landing at MCO
RIGHTOn approach to MCO's south-flow runways, the aircraft descends from the north, and the right side (facing west) reveals Orlando's chain of lakes and the distinctive man-made contours of the Walt Disney World and Universal theme park complexes before touchdown. The left side shows only flat pine scrub and suburban sprawl.
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About This Route
Which side of the plane should I sit on flying from Chicago Midway International (MDW) to Orlando International (MCO)?
Sit on the Right side of the plane for the best views on flights from Chicago to Orlando. While the left side wins a quick Chicago skyline glimpse at takeoff, the right side offers more sustained interest: distant Appalachian foothill terrain in cruise near Tennessee and Georgia, followed by a genuinely distinctive approach over Orlando's lakes and theme park landscape.
What can I see during takeoff from Chicago Midway International in Chicago?
During takeoff from Chicago Midway International (MDW), sit on the Left side for the best views. Departing Midway to the southeast, the left side offers a brief but clear view back toward the Chicago skyline and the edge of Lake Michigan before the aircraft turns onto its southbound track. The right side only shows flat suburban grid streets. Notable sights include: Chicago skyline (Willis Tower, Loop), Lake Michigan shoreline, Midway's grid of suburban neighborhoods.
What can I see when landing at Orlando International in Orlando?
When landing at Orlando International (MCO), sit on the Right side for the best views. On approach to MCO's south-flow runways, the aircraft descends from the north, and the right side (facing west) reveals Orlando's chain of lakes and the distinctive man-made contours of the Walt Disney World and Universal theme park complexes before touchdown. The left side shows only flat pine scrub and suburban sprawl. Notable sights include: Walt Disney World's Bay Lake and Magic Kingdom area, Universal Orlando's resort lagoons, Orlando's chain of lakes, downtown Orlando skyline in the distance.
How long is the flight from Chicago to Orlando?
The flight from Chicago Midway International (MDW) to Orlando International (MCO) takes about 2 hours 20 minutes. The shortest flight path between them is 991 miles (1,595 km); winds and air traffic control usually add a few percent.
What does the Chicago to Orlando flight path pass over?
The route crosses the Ohio River valley, the rolling hills of central Tennessee, and the northern edge of Georgia's Piedmont before descending into flat central Florida.