Left side wins at both ends of the flight. Departing MDW you get the Chicago lakefront and skyline; arriving EWR you get Manhattan, the bay, and the Statue of Liberty. The right seat offers little of comparable interest at either airport.
Flown MDW to EWR? Did we get it right?
Flight Path
Chicago to Newark is 709 miles (1,141 km), a flight of about 1 hour 55 minutes.
The route tracks northeast across northern Indiana and Ohio, passing near South Bend and Toledo. You cross Lake Erie — visible as a broad gray-blue expanse — roughly over the Ohio-Pennsylvania border. The flight then crosses northwestern Pennsylvania and the Pocono Plateau before descending into the New York metro area. The Appalachian ridges of Pennsylvania are visible as parallel forested folds running northeast-southwest, most prominent around the Allegheny Front and the Ridge and Valley province of central Pennsylvania.
Great circle distance and headings ›Phase by phase

Takeoff from MDW
LEFTMDW's most common departures head east or northeast. A left (north) seat gives you a clear view back over the Chicago lakefront, Grant Park, and the downtown skyline as you climb out over the south side. The right seat faces south toward suburban sprawl with little of interest.

Landing at EWR
LEFTEWR's most common approaches from the west come in on runway 22L/22R heading southwest, or runway 29 heading west. On final from the west, the left seat faces south and southeast, giving you Manhattan's skyline, Upper New York Bay, and the Statue of Liberty clearly in view. The right seat looks north toward New Jersey suburbs.
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About This Route
Which side of the plane should I sit on flying from Chicago Midway International (MDW) to Newark Liberty International (EWR)?
Sit on the Left side of the plane for the best views on flights from Chicago to Newark. Left side wins at both ends of the flight. Departing MDW you get the Chicago lakefront and skyline; arriving EWR you get Manhattan, the bay, and the Statue of Liberty. The right seat offers little of comparable interest at either airport.
What can I see during takeoff from Chicago Midway International in Chicago?
During takeoff from Chicago Midway International (MDW), sit on the Left side for the best views. MDW's most common departures head east or northeast. A left (north) seat gives you a clear view back over the Chicago lakefront, Grant Park, and the downtown skyline as you climb out over the south side. The right seat faces south toward suburban sprawl with little of interest. Notable sights include: Chicago downtown skyline, Lake Michigan shoreline, Grant Park/Museum Campus, Chicago River corridor.
What can I see when landing at Newark Liberty International in Newark?
When landing at Newark Liberty International (EWR), sit on the Left side for the best views. EWR's most common approaches from the west come in on runway 22L/22R heading southwest, or runway 29 heading west. On final from the west, the left seat faces south and southeast, giving you Manhattan's skyline, Upper New York Bay, and the Statue of Liberty clearly in view. The right seat looks north toward New Jersey suburbs. Notable sights include: Manhattan skyline, Upper New York Bay, Statue of Liberty, Verrazano-Narrows Bridge.
How long is the flight from Chicago to Newark?
The flight from Chicago Midway International (MDW) to Newark Liberty International (EWR) takes about 1 hour 55 minutes. The shortest flight path between them is 709 miles (1,141 km); winds and air traffic control usually add a few percent.
What does the Chicago to Newark flight path pass over?
The route tracks northeast across northern Indiana and Ohio, passing near South Bend and Toledo. You cross Lake Erie — visible as a broad gray-blue expanse — roughly over the Ohio-Pennsylvania border. The flight then crosses northwestern Pennsylvania and the Pocono Plateau before descending into the New York metro area. The Appalachian ridges of Pennsylvania are visible as parallel forested folds running northeast-southwest, most prominent around the Allegheny Front and the Ridge and Valley province of central Pennsylvania.