While the Disney/Orlando departure view is a nice opener, the right side offers both a glimpse of Appalachian foothills during cruise and a genuinely dramatic Chicago skyline-and-lake view on final approach, giving it more sustained scenic value across the whole flight.
Flown MCO to MDW? Did we get it right?
Flight Path
Orlando to Chicago is 991 miles (1,595 km), a flight of about 2 hours 20 minutes.
Rolling hills and ridgelines of northern Georgia and eastern Tennessee near Chattanooga, the Tennessee River valley, and the transition into the flat farmland of Kentucky, Indiana, and Illinois as the route approaches Chicago.
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Phase by phase
Takeoff from MCO
LEFTDeparting MCO to the north puts Walt Disney World's parks and the Orlando skyline off the left side as the aircraft climbs and banks, giving a brief but very recognizable view before the terrain flattens into farmland and pine scrub.
Landing at MDW
RIGHTOn approach into Midway from the south, the flight path curves near Lake Michigan before turning onto final, putting the Chicago skyline and the lake's shoreline on the right side during descent — a much stronger visual payoff than the flat farmland on the opposite side.
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About This Route
Which side of the plane should I sit on flying from Orlando International (MCO) to Chicago Midway International (MDW)?
Sit on the Right side of the plane for the best views on flights from Orlando to Chicago. While the Disney/Orlando departure view is a nice opener, the right side offers both a glimpse of Appalachian foothills during cruise and a genuinely dramatic Chicago skyline-and-lake view on final approach, giving it more sustained scenic value across the whole flight.
What can I see during takeoff from Orlando International in Orlando?
During takeoff from Orlando International (MCO), sit on the Left side for the best views. Departing MCO to the north puts Walt Disney World's parks and the Orlando skyline off the left side as the aircraft climbs and banks, giving a brief but very recognizable view before the terrain flattens into farmland and pine scrub. Notable sights include: Magic Kingdom and Epcot's geodesic dome, Bay Lake and the Seven Seas Lagoon, downtown Orlando's skyline, Lake Apopka.
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 Midway from the south, the flight path curves near Lake Michigan before turning onto final, putting the Chicago skyline and the lake's shoreline on the right side during descent — a much stronger visual payoff than the flat farmland on the opposite side. Notable sights include: Chicago skyline (Willis Tower, Sears/Willis cluster), Lake Michigan shoreline, Midway's grid-pattern neighborhoods, the Chicago Sanitary and Ship Canal.
How long is the flight from Orlando to Chicago?
The flight from Orlando International (MCO) to Chicago Midway International (MDW) 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 Orlando to Chicago flight path pass over?
Rolling hills and ridgelines of northern Georgia and eastern Tennessee near Chattanooga, the Tennessee River valley, and the transition into the flat farmland of Kentucky, Indiana, and Illinois as the route approaches Chicago.