Right-side seats offer the most consistent scenic value: excellent coastal views during takeoff from Portland, and during the westbound cruise across New England and New York, right-side passengers see the Appalachian terrain, valleys, and ridgelines. While left-side has the advantage on landing into Chicago, the takeoff scenery from Portland is more distinctive and memorable.
Flight Path
The flight path crosses the Appalachian Mountains (visible as ridgelines and valleys in upstate New York and Pennsylvania), the Hudson River valley near New York City, the Finger Lakes region of New York, and eventually transitions to the flatter terrain of Ohio and Indiana as the aircraft approaches the Midwest. Lake Erie may be visible to the north depending on exact routing. The Great Lakes region becomes increasingly prominent in the final hour of flight.
Phase by phase
Takeoff from
Landing at
Landmarks on this routeAll landmarks →
.jpeg?width=600)
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 Portland International Jetport (PWM) to Chicago Midway International (MDW)?
Sit on the Right side of the plane for the best views on flights from Portland to Chicago. Right-side seats offer the most consistent scenic value: excellent coastal views during takeoff from Portland, and during the westbound cruise across New England and New York, right-side passengers see the Appalachian terrain, valleys, and ridgelines. While left-side has the advantage on landing into Chicago, the takeoff scenery from Portland is more distinctive and memorable.
What can I see during takeoff from Portland International Jetport in Portland?
During takeoff from Portland International Jetport (PWM), sit on the Right side for the best views. Right-side seats offer views of Casco Bay and the Maine coastline during the initial climb-out. The aircraft typically departs to the northeast or east, and right-side passengers will see the rocky Atlantic coast, islands, and the transition from coastal Maine to inland terrain. Notable sights include: Casco Bay with its scattered islands, the Maine coastline and rocky shores, Sebago Lake visible inland to the west, White Mountains of New Hampshire appearing on the distant horizon to the northwest.
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. Left-side seats provide excellent views during the approach to Midway. The aircraft descends from the northeast, and left-side passengers see Lake Michigan, downtown Chicago's skyline, and the urban grid of the city. The approach path brings the lake into clear view on the left side. Notable sights include: Lake Michigan's shoreline and blue water, downtown Chicago skyline with Willis Tower and clustered high-rises, the Chicago River visible as it cuts through the downtown area, residential neighborhoods and industrial areas of the South Side spreading inland.
How long is the flight from Portland to Chicago?
The flight from Portland International Jetport (PWM) to Chicago Midway International (MDW) takes Approximately 4 hours 15 minutes.
What does the Portland to Chicago flight path pass over?
The flight path crosses the Appalachian Mountains (visible as ridgelines and valleys in upstate New York and Pennsylvania), the Hudson River valley near New York City, the Finger Lakes region of New York, and eventually transitions to the flatter terrain of Ohio and Indiana as the aircraft approaches the Midwest. Lake Erie may be visible to the north depending on exact routing. The Great Lakes region becomes increasingly prominent in the final hour of flight.