Sit on the Right side of the plane for the best views on flights from Chicago to Portland. The right side captures the dramatic Chicago lakefront departure, and during the flight over Lake Erie's southern shore and upstate New York, the right side also picks up views of the Finger Lakes region and the Connecticut River valley on descent. The left side has the edge only at landing, but the takeoff and en-route views favor right overall.

During takeoff from Chicago Ohare International (ORD), sit on the Right side for the best views. ORD's most common eastbound departures use runways 10R/10L heading east, putting the Chicago skyline and Lake Michigan on the right side. You'll get a clear view of the downtown lakefront as the aircraft climbs and turns northeast toward Michigan. Notable sights include: Chicago downtown skyline, Lake Michigan shoreline, Navy Pier area, Indiana Dunes coastline to the southeast.

When landing at Portland International Jetport (PWM), sit on the Left side for the best views. PWM typically uses runway 29 for westerly approaches or runway 11 for easterly arrivals. On the common approach from the west, the left side gives you views over Casco Bay's islands and the Portland peninsula as you descend. The right side faces inland toward forest. Notable sights include: Casco Bay and its island chain, Portland peninsula and harbor, Sebago Lake to the northwest, White Mountains on the distant western horizon.

The flight from Chicago Ohare International (ORD) to Portland International Jetport (PWM) takes Approximately 2 hours 15 minutes to 2 hours 30 minutes.

The flight tracks northeast over southern Michigan, crosses Lake Erie near its eastern end or over northern Ohio, then passes over upstate New York including the Finger Lakes region, the Adirondack foothills, and the Green Mountains of Vermont before descending over coastal New Hampshire and southern Maine toward Casco Bay