Sit on the Right side of the plane for the best views on flights from Chicago to Lisbon. The Lisbon arrival on the right side is the more spectacular and unique view of the two. Chicago's lakefront is impressive but familiar; the Tagus estuary with the 25 de Abril Bridge and Lisbon's hillside cityscape on approach is genuinely striking and less commonly seen. The right side also captures the Atlantic coastline of Portugal during descent.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare's primary eastbound departures on runways 10L/10R put the left side facing north toward downtown Chicago. You get a clear view of the lakefront, Grant Park, and the Loop skyline as the aircraft climbs and banks eastward over Lake Michigan. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Grant Park and Museum Campus, Navy Pier.

When landing at Lisboa (LIS), sit on the Right side for the best views. Lisbon's primary landing approach on runway 03 comes in from the south over the Tagus estuary. The right side faces west and southwest, giving you a direct view of the Tagus River mouth, the 25 de Abril Bridge, and the city of Lisbon spread across its hills before touchdown. Notable sights include: Tagus River (Tejo) estuary, 25 de Abril Bridge, Lisbon city hills and waterfront, Cristo Rei statue on the south bank.

The flight from Chicago Ohare International (ORD) to Lisboa (LIS) takes Approximately 8 to 9 hours.

The route tracks northeast over the Great Lakes region, then crosses southern Canada and Newfoundland before heading out over the North Atlantic. The midpoint falls over the open North Atlantic Ocean roughly south of Greenland and Iceland. As the flight approaches Europe, the west coast of Ireland and Cornwall in southwest England may be visible depending on routing, followed by the Bay of Biscay and the northern coast of the Iberian Peninsula before descending toward Lisbon.