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HPN → ORD
Which side of the plane to sit from Westchester County Airport (White Plains) to Chicago O'Hare International Airport (Chicago)?
Left Side of the Plane
The left side is the preferred choice for this route because it offers a strategic view of the Chicago skyline during the final approach into O'Hare, alongside excellent views of the Appalachian mountain folds.
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Manhattan Horizon
Shortly after takeoff from HPN, look south to see the distant skyline of New York City and the George Washington Bridge.
Appalachian Ridges
Dramatic views of the unique fold-and-thrust belt patterns across central Pennsylvania.
Susquehanna River
A clear view of the wide, winding river as it cuts through the mountain gaps near Harrisburg.
Chicago Skyline
On the typical approach to ORD, the left side provides a stunning panorama of the Willis Tower and the Loop.
Sit on the left for the iconic Chicago skyline view, which usually appears as the plane turns west over Lake Michigan or the southern suburbs. On evening flights, the sun sets to the west, providing a dramatic backlight to the Appalachian ridges during the middle of the journey.
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Hudson River Valley
Beautiful views of the Hudson River and the lush greenery of the Bear Mountain area immediately after departure.
The Poconos
Aerial perspectives of the resort lakes and rolling forested hills of Northeastern Pennsylvania.
Lake Erie Shoreline
Glimpses of the Great Lakes coastline, including the industrial and urban landscapes near Cleveland.
Lake Michigan Expanse
A vast view of the deep blue water and the North Shore suburbs as the flight descends into the Chicago area.
Choose the right side if you prefer a morning flight to avoid the direct glare of the sun. This side offers better views of the Hudson Valley and the Great Lakes shoreline. In winter, the frozen edges of Lake Erie and Lake Michigan are particularly striking from this vantage point.
Book Hotels in ChicagoDistance: 1,185 km (736 miles)
Approximate Flight Time: 1 hr 35 min
Departure: HPN (41.06700134277344, -73.70760345458984)
Arrival: ORD (41.9786, -87.9048)
Route Type: Domestic
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