Sit on the Right side of the plane for the best views on flights from Chicago to Montreal. The right side delivers the dramatic Chicago skyline and Lake Michigan on departure, which is the single most visually striking moment of this flight. During cruise the route passes over relatively flat terrain in Ontario and Quebec with limited dramatic features on either side, so the takeoff view is the deciding factor.

During takeoff from Chicago Ohare International (ORD), sit on the Right side for the best views. ORD's most common departures head east or northeast on runways 10/28 or 9R/27L. A right-side seat on a northeast departure gives you a clear view of downtown Chicago's skyline, the lakefront, and Lake Michigan as the aircraft banks right over the city. The Willis Tower and the dense Loop district are unmistakable from this angle. Notable sights include: Downtown Chicago skyline (Willis Tower, John Hancock), Lake Michigan shoreline, Chicago River grid, Grant Park and Museum Campus.

When landing at St Hubert (YHU), sit on the Left side for the best views. YHU sits south of Montreal, and aircraft typically approach from the west or southwest on runway 24L/R. A left-side seat gives you the best view of the St. Lawrence River, the island of Montreal, and the distinctive green dome of Mont Royal as you descend. The broad river and the island's urban density are clearly visible on approach. Notable sights include: St. Lawrence River, Island of Montreal, Mont Royal (233m forested hill), Longueuil and South Shore urban grid.

The flight from Chicago Ohare International (ORD) to St Hubert (YHU) takes Approximately 1 hour 45 minutes to 2 hours.

The flight tracks northeast over southern Ontario, crossing Lake Erie's northern shore near Hamilton, then over the Ontario farmland and forest belt north of Lake Ontario. The route passes near Kingston where Lake Ontario narrows toward the St. Lawrence River, then crosses into Quebec over the Laurentian lowlands before descending toward Montreal. The terrain is predominantly flat agricultural land and boreal forest with few dramatic elevation changes.