The left side captures both scenic bookends of the flight — Boston Harbor on departure and Lake Michigan with the Chicago skyline on arrival — while the cruise portion over the flat Northeast and Midwest offers little differentiation between sides.
Flown BOS to MDW? Did we get it right?
Flight Path
Boston to Chicago is 858 miles (1,381 km), a flight of about 2 hours 10 minutes.
Rolling hills of upstate New York and the flat farmland of Ohio and Indiana, with occasional glimpses of the Mohawk Valley and the southern shore of Lake Erie depending on routing.
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Phase by phase
Takeoff from BOS
LEFTNoise-abatement departures from BOS climb out over Boston Harbor before banking to head west toward Chicago, putting the harbor islands and downtown Boston skyline on the left side during the turn.
Landing at MDW
LEFTArrivals into MDW commonly set up on runway 13C, descending from the northwest and turning onto final over the northern lakefront, which puts Lake Michigan and the Chicago skyline on the left side of the aircraft.
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About This Route
Which side of the plane should I sit on flying from General Edward Lawrence Logan International (BOS) to Chicago Midway International (MDW)?
Sit on the Left side of the plane for the best views on flights from Boston to Chicago. The left side captures both scenic bookends of the flight — Boston Harbor on departure and Lake Michigan with the Chicago skyline on arrival — while the cruise portion over the flat Northeast and Midwest offers little differentiation between sides.
What can I see during takeoff from General Edward Lawrence Logan International in Boston?
During takeoff from General Edward Lawrence Logan International (BOS), sit on the Left side for the best views. Noise-abatement departures from BOS climb out over Boston Harbor before banking to head west toward Chicago, putting the harbor islands and downtown Boston skyline on the left side during the turn. Notable sights include: Boston Harbor Islands, Downtown Boston skyline, Logan Airport's harbor-side runways.
What can I see when landing at Chicago Midway International in Chicago?
When landing at Chicago Midway International (MDW), sit on the Left side for the best views. Arrivals into MDW commonly set up on runway 13C, descending from the northwest and turning onto final over the northern lakefront, which puts Lake Michigan and the Chicago skyline on the left side of the aircraft. Notable sights include: Lake Michigan shoreline, Chicago skyline (Willis Tower, Loop), Navy Pier, Midway's residential grid.
How long is the flight from Boston to Chicago?
The flight from General Edward Lawrence Logan International (BOS) to Chicago Midway International (MDW) takes about 2 hours 10 minutes. The shortest flight path between them is 858 miles (1,381 km); winds and air traffic control usually add a few percent.
What does the Boston to Chicago flight path pass over?
Rolling hills of upstate New York and the flat farmland of Ohio and Indiana, with occasional glimpses of the Mohawk Valley and the southern shore of Lake Erie depending on routing.