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ORD destination photo
HPN destination photo

ORDHPN

Our Recommendation
8.5

Right Side of the Plane

The right side offers the most iconic urban vistas, featuring the full Chicago skyline immediately after departure and a spectacular view of the New York City skyline and Long Island Sound during the descent into Westchester.

Right Side Highlights
8.5
🏙️

Chicago Skyline

Unrivaled views of the Willis Tower, Millennium Park, and the Navy Pier if departing to the east or turning south.

🏭

Industrial Great Lakes

Bird's-eye view of the steel mills in Gary, Indiana, and the shoreline of Cleveland, Ohio.

🌲

Allegheny Plateau

Rugged, ridged terrain of northern Pennsylvania, particularly striking during the autumn foliage season.

🗽

Manhattan Skyline

On the final approach to HPN, look south to see the dense cluster of skyscrapers in Midtown and Lower Manhattan.

🛥️

Long Island Sound

Deep blue waters and the affluent coastal towns of Connecticut and New York just before touchdown.

Request a seat well ahead of the wing to ensure the engine doesn't block the NYC skyline view on approach. Afternoon flights offer the best lighting for photography of the Chicago lakefront and the Manhattan skyline.

Left Side Highlights
7.8
🌊

Lake Michigan Shoreline

Vast views of the lake's northern coast and the suburbs of Chicago's North Shore during the initial climb.

🍷

Finger Lakes Region

Glacial lakes including Seneca and Cayuga are often visible as thin, dark slivers among the New York landscape.

⛰️

Catskill Mountains

Dense forest canopies and rolling peaks of the Catskills as the aircraft begins its descent into the Hudson Valley.

🌉

Hudson River Valley

A beautiful perspective of the wide river as it winds through the Highlands toward the Tappan Zee.

For morning flights, sit on this side to avoid the direct glare of the sun. This side is superior for observing the natural topography and the transition from the Midwest plains to the Appalachian foothills.

Top Activities in White Plains
Route Information

Distance: 1,185 km (736 miles)

Approximate Flight Time: 1 hr 35 min

Departure: ORD (41.9786, -87.9048)

Arrival: HPN (41.06700134277344, -73.70760345458984)

Route Type: Domestic

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