Boston to Chicago flight path: BOS to ORD

Sit on the right side of the plane

Which side of the plane?

Pick the window seat with the view. 13,500 routes answered — landmarks, coastlines and cities, wing by wing.

Flight time3h 15m
Distance864
Heading274° → 263°
Best side
RightMostly right
★ 2.5 left·★ 3.0 right

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.

Takeoff · BOSLEFTBoston Harbor Islands, Downtown Boston skyline, South Boston waterfront
Landing · ORDRIGHTLake Michigan shoreline, Chicago downtown skyline (Willis Tower, Loop)

Flight Path

Flight path overview

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

Aerial window seat view during takeoff from Boston (left side) — Boston Harbor Islands, Downtown Boston skyline, South Boston waterfront, Logan Airport runways receding below

Takeoff from BOS

LEFT

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.

Boston Harbor IslandsDowntown Boston skylineSouth Boston waterfrontLogan Airport runways receding below
Aerial window seat view during landing at Chicago (right side) — Lake Michigan shoreline, Chicago downtown skyline (Willis Tower, Loop), Navy Pier, O'Hare's runway complex ahead

Landing at ORD

RIGHT

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.

Lake Michigan shorelineChicago downtown skyline (Willis TowerLoop)Navy Pier

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