Sit on the Right side of the plane for the best views on flights from Lisbon to Chicago. The right side delivers the most dramatic single moment of the flight — the Tagus estuary and Lisbon cityscape on departure — and also captures the Atlantic crossing's northern light. The Chicago approach views on the left are excellent but shorter in duration. Right side wins on total scenic value.

During takeoff from Lisboa (LIS), sit on the Right side for the best views. Lisbon's main departure runway 21 sends aircraft southwest over the Tagus estuary before turning northwest. Right side seats get the broad Tagus estuary, the 25 de Abril suspension bridge, and the city's historic hilltop districts as the aircraft banks north. Left side faces inland toward flat suburban sprawl. Notable sights include: Tagus River estuary, 25 de Abril Bridge, Belém Tower area along the riverfront, Cristo Rei statue on the south bank.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare predominantly uses runways oriented east-west or northwest-southeast. Approaches from the east on runway 10 or from the northeast bring aircraft over the Chicago lakefront. Left side seats get Lake Michigan, the downtown Chicago skyline including Willis Tower and the lakefront, and the dense urban grid of the North Side. Notable sights include: Lake Michigan shoreline, Chicago downtown skyline (Willis Tower, John Hancock Center), Chicago River mouth at the lakefront, dense urban grid of the North Side.

The flight from Lisboa (LIS) to Chicago Ohare International (ORD) takes Approximately 9 to 10 hours.

The flight tracks northwest from Lisbon across the Atlantic on a great circle route, passing south of the Azores archipelago (visible as small volcanic islands if routing passes close), then over the open North Atlantic for the majority of the flight. The route crosses Newfoundland or southern Labrador, where the rugged Canadian Shield, boreal forest, and coastal fjords of the Labrador coast may be visible. The flight then crosses the Great Lakes region, with Lake Erie and Lake Michigan visible on descent into Chicago.