Portland to Chicago is 898 miles (1,444 km), a flight of about 2 hours 45 minutes.
The right side captures the only real scenic anchors of this route: the Maine coastline near Portland at departure and the Lake Michigan/Chicago skyline view on arrival, whereas the left side offers mostly featureless New England and Midwest terrain throughout cruise.
Flight Path
Rolling hills of central New York, the Finger Lakes region, and the flat farmland of northern Ohio and Indiana beneath the cruise track
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Phase by phase
Takeoff from PWM
RIGHTDeparting PWM on runway 29, the climb-out gives a brief glimpse of Casco Bay and Portland's harbor islands off the right side before the aircraft turns west, while the left side shows only inland Maine forest with no distinguishing features.
Landing at ORD
RIGHTOn approach into ORD from the east, the right side offers views across the southern tip of Lake Michigan and the Chicago skyline before the final turn onto the east-west runways, while the left side shows only flat Illinois farmland.
Landmarks on this routeAll landmarks →
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About This Route
Which side of the plane should I sit on flying from Portland International Jetport (PWM) to Chicago Ohare International (ORD)?
Sit on the Right side of the plane for the best views on flights from Portland to Chicago. The right side captures the only real scenic anchors of this route: the Maine coastline near Portland at departure and the Lake Michigan/Chicago skyline view on arrival, whereas the left side offers mostly featureless New England and Midwest terrain throughout cruise.
What can I see during takeoff from Portland International Jetport in Portland?
During takeoff from Portland International Jetport (PWM), sit on the Right side for the best views. Departing PWM on runway 29, the climb-out gives a brief glimpse of Casco Bay and Portland's harbor islands off the right side before the aircraft turns west, while the left side shows only inland Maine forest with no distinguishing features. Notable sights include: Casco Bay, Portland Harbor islands, Maine coastline.
What can I see when landing at Chicago Ohare International in Chicago?
When landing at Chicago Ohare International (ORD), sit on the Right side for the best views. On approach into ORD from the east, the right side offers views across the southern tip of Lake Michigan and the Chicago skyline before the final turn onto the east-west runways, while the left side shows only flat Illinois farmland. Notable sights include: Lake Michigan shoreline, Chicago skyline, Willis Tower.
How long is the flight from Portland to Chicago?
The flight from Portland International Jetport (PWM) to Chicago Ohare International (ORD) takes about 2 hours 45 minutes. The shortest flight path between them is 898 miles (1,444 km); winds and air traffic control usually add a few percent.
What does the Portland to Chicago flight path pass over?
Rolling hills of central New York, the Finger Lakes region, and the flat farmland of northern Ohio and Indiana beneath the cruise track