Sit on the Left side of the plane for the best views on flights from Portland to Chicago. Left side delivers the best views at both ends of the flight — Casco Bay's island-studded coastline on departure and Chicago's lakefront skyline on approach. The mid-flight segment over rural New England and upstate New York is scenic but less dramatic on either side.

During takeoff from Portland International Jetport (PWM), sit on the Left side for the best views. PWM's primary departure runway is 29 (heading west-northwest). A left-side seat faces south, giving views over Casco Bay's islands and the Portland peninsula as you climb out. The Atlantic coastline and the outer islands of Casco Bay are clearly visible before the aircraft turns west. Notable sights include: Casco Bay islands (including Peaks Island and Long Island), Portland peninsula and Back Cove, Old Orchard Beach coastline to the south, Sebago Lake visible to the west as altitude increases.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare arrivals from the east typically use runways oriented east-west (runways 10/28 or 9R/27L). On approach from the east, a left-side seat faces south over the Chicago metropolitan area, giving clear views of the downtown Loop skyline, Lake Michigan's shoreline, and the dense urban grid of the south and west sides. Notable sights include: Chicago Loop skyline and lakefront, Lake Michigan shoreline and Grant Park area, O'Hare's distinctive runway complex visible below on final, suburban Cook County grid stretching to the horizon.

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

The flight tracks west-southwest over the White Mountains of New Hampshire (visible as a wrinkled highland mass early in cruise), then over the Adirondacks of upstate New York, Lake Ontario's southern shoreline may be visible to the north, followed by the flat agricultural plains of northern Indiana before descending into the Chicago metro area