Sit on the Left side of the plane for the best views on flights from London to Chicago. Left side wins at both ends of the flight. Over the North Atlantic the views are largely ocean with occasional Greenland ice sheet glimpses on the left side as the great circle route arcs north, and on descent into Chicago the left side delivers the Lake Michigan and skyline approach. Left is the clear choice for the full journey.

During takeoff from Heathrow (LHR), sit on the Left side for the best views. Heathrow departures heading west on runways 27L/27R give the left (south) side a view back over central London as the aircraft banks. You get the Thames snaking eastward through the city, with the urban sprawl of west London spread out clearly below. The right side faces north toward the relatively featureless suburbs of Slough and Uxbridge. Notable sights include: River Thames curving through west London, Windsor Castle and Windsor Great Park to the southwest, Wembley Stadium arch visible to the north-northeast, the M25 orbital motorway cutting across the landscape.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. Flights from London typically approach O'Hare from the northeast on runways 10L/10R or 9L/9R, meaning the left (north) side looks out over Lake Michigan's southern shoreline and the Chicago lakefront. You get a clear view of the downtown skyline, Grant Park, and the lakefront as the aircraft descends. The right side faces southwest toward flat suburban sprawl with no comparable features. Notable sights include: Lake Michigan southern shoreline, Chicago downtown skyline including Willis Tower and the Loop, Grant Park and Millennium Park green strip along the lakefront, the distinctive grid of Chicago's street layout.

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

The great circle route arcs well north, passing over Ireland's west coast, then the North Atlantic with possible views of southern Greenland's ice sheet and glaciated coastline, then the Labrador coast of Canada, Hudson Bay to the north, Quebec and Ontario boreal forest, and the Great Lakes region before descending into Chicago. The most visually dramatic midpoint feature is the southern Greenland ice sheet if cloud cover permits, visible as a vast white expanse from cruising altitude.