Sit on the Left side of the plane for the best views on flights from London to Chicago. The right side wins at takeoff with Windsor and the Thames, but the left side delivers the more dramatic payoff: the southern Lake Michigan coastline, the full Chicago skyline on approach, and during the transatlantic cruise, left-side seats get better views of southern Greenland's ice sheet and Labrador's fjord coastline on the great circle route.

During takeoff from Heathrow (LHR), sit on the Right side for the best views. Heathrow departures on the westbound runways (09L/09R departing eastward then turning west, or 27L/27R departing westward) typically route aircraft over or near central London when departing east, or over Windsor and the Thames Valley heading west. Right-side seats on a westbound departure get Windsor Castle, the Thames bends, and the Berkshire countryside. Left side faces north toward Slough and suburban sprawl. Notable sights include: Windsor Castle and Windsor Great Park, Thames River bends near Staines and Runnymede, Heathrow's terminal complex receding behind, Berkshire/Chiltern Hills rolling into the distance.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. Midway sits on Chicago's South Side, and aircraft typically approach from the east or northeast on runway 31C/31L heading northwest, or from the south on runway 04R heading northeast. A northeast approach brings the left side over Lake Michigan's southern tip, the Chicago lakefront skyline, and Grant Park before crossing the South Side grid into Midway. Right side faces inland suburban sprawl. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock) seen from the south, southern tip of Lake Michigan, the dense street grid of Chicago's South Side, Midway Airport's distinctive compact layout.

The flight from Heathrow (LHR) to Chicago Midway International (MDW) takes Approximately 8 to 9 hours westbound.

The great circle route from LHR to MDW tracks northwest over Ireland, then across the North Atlantic passing south of Iceland, over the southern tip of Greenland with its ice sheet and coastal fjords visible, then across Labrador and Quebec's boreal forest and lake-studded Canadian Shield, clipping the northern Great Lakes region before descending into Chicago. Hudson Bay may be visible to the north at cruise altitude. The route avoids the worst of the jet stream by tracking a higher latitude arc.