New York to Chicago flight path: LGA to MDW

Sit on the Right side of the plane for the best views on flights from New York to Chicago. The right side bookends the short flight with two genuine skyline views — Manhattan on departure and Chicago's Loop with Lake Michigan on arrival — while the cruise portion over Pennsylvania and Ohio is flat and unremarkable on either side.

During takeoff from La Guardia (LGA), sit on the Right side for the best views. LaGuardia departures heading toward Chicago typically climb out and bank over the East River, putting the Manhattan skyline and Hudson River on the right side of the aircraft. The left side mostly shows the flat suburban sprawl of Queens and Long Island with little to distinguish it. Notable sights include: Manhattan skyline, East River, Central Park, Hudson River mouth.

When landing at Chicago Midway International (MDW), sit on the Right side for the best views. Arrivals into Midway from the east often get vectored north of the field before turning onto final, briefly putting the Chicago Loop skyline and Lake Michigan shoreline on the right side of the plane. The left side during descent mostly overlooks flat Indiana and southwest Chicago suburbs with no major landmarks. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Willis Tower, Midway's grid of southwest-side neighborhoods.

The flight from La Guardia (LGA) to Chicago Midway International (MDW) takes 2h 10m.

The route crosses the rolling Allegheny Plateau of northern Pennsylvania, then flattens into farmland across Ohio and Indiana, with the southern shoreline of Lake Erie sometimes visible in the distance to the north.