Chicago to Portland is 898 miles (1,444 km), a flight of about 2 hours 15 minutes.
The left side benefits from the Great Lakes crossing near Erie, distant views of the Adirondacks and southern Green/White Mountains during cruise, and a genuinely scenic coastal descent into Portland over Casco Bay, giving it more variety and drama than the flatter farmland visible from the right.
Flight Path
Southern Lake Erie shoreline, upstate New York farmland, foothills of the Adirondacks and Green Mountains, and the rolling hills of southern New Hampshire before descending into coastal Maine
Great circle distance and headings ›
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Phase by phase
Takeoff from ORD
RIGHTO'Hare departures heading east or turning northeast put Chicago's skyline and the Lake Michigan shoreline on the right side of the aircraft, giving a brief but distinctive urban view before the plains take over.
Landing at PWM
LEFTOn approach into Portland, the routing over the Maine coastline puts Casco Bay's islands and the rocky shoreline on the left side as the plane descends toward runway 29, offering a scenic coastal view rare for a short domestic hop.
Landmarks on this routeAll landmarks →
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About This Route
Which side of the plane should I sit on flying from Chicago Ohare International (ORD) to Portland International Jetport (PWM)?
Sit on the Left side of the plane for the best views on flights from Chicago to Portland. The left side benefits from the Great Lakes crossing near Erie, distant views of the Adirondacks and southern Green/White Mountains during cruise, and a genuinely scenic coastal descent into Portland over Casco Bay, giving it more variety and drama than the flatter farmland visible from the right.
What can I see during takeoff from Chicago Ohare International in Chicago?
During takeoff from Chicago Ohare International (ORD), sit on the Right side for the best views. O'Hare departures heading east or turning northeast put Chicago's skyline and the Lake Michigan shoreline on the right side of the aircraft, giving a brief but distinctive urban view before the plains take over. Notable sights include: Chicago skyline, Lake Michigan shoreline, Navy Pier area, O'Hare's runway grid.
What can I see when landing at Portland International Jetport in Portland?
When landing at Portland International Jetport (PWM), sit on the Left side for the best views. On approach into Portland, the routing over the Maine coastline puts Casco Bay's islands and the rocky shoreline on the left side as the plane descends toward runway 29, offering a scenic coastal view rare for a short domestic hop. Notable sights include: Casco Bay islands, Portland Head Light area, Maine coastline, Fore River estuary.
How long is the flight from Chicago to Portland?
The flight from Chicago Ohare International (ORD) to Portland International Jetport (PWM) takes about 2 hours 15 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 Chicago to Portland flight path pass over?
Southern Lake Erie shoreline, upstate New York farmland, foothills of the Adirondacks and Green Mountains, and the rolling hills of southern New Hampshire before descending into coastal Maine