While the Boston harbor departure gives the left side a strong opening scene, the right side accumulates more total scenery: a glimpse of Lake Erie's south shore during cruise plus Lake Michigan and the Chicago skyline on arrival, making it the more consistently rewarding side for this route.
Flight Path
Berkshire foothills of western Massachusetts, the Finger Lakes region of upstate New York, the south shore of Lake Erie near Erie, PA and Cleveland, and the flat farmland of northern Ohio and Indiana as the route levels out toward Chicago
Great circle distance and headings ›Phase by phase

Takeoff from BOS
LEFTBOS noise-abatement departures climb north over Boston Harbor before banking west toward Chicago, and that turn puts the harbor islands and downtown Boston skyline squarely on the left side of the aircraft. The right side mostly sees open water and the South Shore during the same maneuver.

Landing at ORD
RIGHTArrivals into ORD from the east typically track just south of Lake Michigan before turning onto the east-west runways, putting the lake and the Chicago skyline on the right side of the cabin during the descent. The left side instead just shows flat western suburbs and highway grids.
Landmarks on this routeAll landmarks →
Will your flight be in sunlight?
See exactly which side of the plane gets sun and shade at your departure time.
About This Route
Which side of the plane should I sit on flying from General Edward Lawrence Logan International (BOS) to Chicago Ohare International (ORD)?
Sit on the Right side of the plane for the best views on flights from Boston to Chicago. While the Boston harbor departure gives the left side a strong opening scene, the right side accumulates more total scenery: a glimpse of Lake Erie's south shore during cruise plus Lake Michigan and the Chicago skyline on arrival, making it the more consistently rewarding side for this route.
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. BOS noise-abatement departures climb north over Boston Harbor before banking west toward Chicago, and that turn puts the harbor islands and downtown Boston skyline squarely on the left side of the aircraft. The right side mostly sees open water and the South Shore during the same maneuver. Notable sights include: Boston Harbor Islands, Downtown Boston skyline, South Boston waterfront, Logan Airport runways receding below.
What can I see when landing at Chicago Ohare International in Chicago?
When landing at Chicago Ohare International (ORD), sit on the Right side for the best views. Arrivals into ORD from the east typically track just south of Lake Michigan before turning onto the east-west runways, putting the lake and the Chicago skyline on the right side of the cabin during the descent. The left side instead just shows flat western suburbs and highway grids. Notable sights include: Lake Michigan shoreline, Chicago downtown skyline (Willis Tower, Loop), Navy Pier, O'Hare's runway complex ahead.
How long is the flight from Boston to Chicago?
The flight from General Edward Lawrence Logan International (BOS) to Chicago Ohare International (ORD) takes 3h15m.
What does the Boston to Chicago flight path pass over?
Berkshire foothills of western Massachusetts, the Finger Lakes region of upstate New York, the south shore of Lake Erie near Erie, PA and Cleveland, and the flat farmland of northern Ohio and Indiana as the route levels out toward Chicago