Sit on the Left side of the plane for the best views on flights from Montreal to Chicago. Left side wins both ends of this flight. You get the St. Lawrence River and Montreal cityscape on departure, and the Lake Michigan shoreline with the Chicago skyline on approach. The right side sees mostly flat Ontario and Indiana farmland throughout, which is considerably less interesting.

During takeoff from Montreal International Dorval (YUL), sit on the Left side for the best views. Departing Montreal, aircraft typically use runways oriented northeast-southwest. A left (south-facing) seat gives you a clear view over the St. Lawrence River and the Montreal island cityscape including downtown and Mount Royal as you climb out westbound. The river is a dominant, unmistakable feature from this side. Notable sights include: St. Lawrence River, Mount Royal and downtown Montreal skyline, Île de Montréal shoreline, Lac Saint-Louis to the southwest.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. Approaching O'Hare from the east-northeast, aircraft typically land on runways oriented east-west or northwest-southeast. A left (south-facing) seat gives you the best view of Lake Michigan's southern shoreline, the Chicago downtown skyline, and the dense urban grid of the city as you descend. The lakefront is the defining visual feature of this approach. Notable sights include: Lake Michigan southern shoreline, Chicago downtown skyline (Willis Tower, John Hancock), Chicago River grid visible from altitude, suburban Cook County grid stretching west.

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

The flight tracks southwest over flat southern Ontario farmland, crossing Lake Erie's northern shore near the Ontario-Michigan border region, then over northern Indiana's agricultural plains before descending into Chicago. Lake Erie may be briefly visible from either side depending on exact routing, but the terrain is predominantly flat and agricultural through Ontario and Indiana with few dramatic features at cruising altitude.