Sit on the Right side of the plane for the best views on flights from Chicago to Montreal. The right side delivers the most dramatic single moment of the flight — the Chicago lakefront and skyline on departure — and also captures Lake Erie and Lake Ontario as the route tracks northeast. The left side has the better Montreal landing view, but the Chicago departure on the right is the highlight of this route.

During takeoff from Chicago Ohare International (ORD), sit on the Right side for the best views. ORD's most common eastbound departures (runways 10L/10R) head east-southeast, putting the Chicago skyline and Lake Michigan on the right side. You get a clear view of the downtown Loop, Grant Park, and the lakefront as the aircraft climbs out over the suburbs. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Grant Park/Museum Campus, Wrigley Field area in the north lakefront.

When landing at Montreal International Dorval (YUL), sit on the Left side for the best views. YUL's most common approach from the west uses runway 24L/24R, bringing aircraft in from the southwest. The left side gives views over the St. Lawrence River, the Montreal island, and the city's downtown core including Mont Royal as you descend. Notable sights include: Mont Royal (the hill at the city's center), St. Lawrence River, Montreal downtown skyline, Île de Montréal urban grid.

The flight from Chicago Ohare International (ORD) to Montreal International Dorval (YUL) takes Approximately 1 hour 45 minutes to 2 hours.

The route tracks northeast over southern Michigan, crossing Lake Erie near the Ontario border, then over southwestern Ontario farmland, Lake Ontario near Kingston, and the St. Lawrence River valley before descending into Montreal. Lake Erie and Lake Ontario are both potentially visible from altitude as large dark water bodies flanking the route.