Sit on the Left side of the plane for the best views on flights from Chicago to Sao Paulo. The left side delivers the most dramatic single moment of the flight — the Chicago skyline and Lake Michigan on departure — and also captures the Atlantic coastline of Brazil during the southbound leg as the route passes near the coast. The right side has a good GRU landing view but the left side wins on total scenic value.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. ORD's most common departures head southeast or east on runways 10R/10L, putting the Chicago skyline and Lake Michigan on the left side. You get a clear view of the downtown Loop, Grant Park, and the lakefront as the aircraft banks south. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Grant Park and Museum Campus, Indiana Dunes coastline to the southeast.

When landing at Guarulhos (GRU), sit on the Right side for the best views. GRU sits northeast of São Paulo, and aircraft typically approach from the north or northeast on runways 09R/09L or 27L/27R. A right-side seat gives views over the Serra da Cantareira hills and the sprawling São Paulo metropolitan grid as you descend from the north. Notable sights include: Serra da Cantareira forested ridge, São Paulo metropolitan sprawl, Tietê River snaking through the city, Guarulhos urban area directly below on final approach.

The flight from Chicago Ohare International (ORD) to Guarulhos (GRU) takes Approximately 10 to 11 hours.

The route tracks southeast over the Gulf of Mexico, crosses the Caribbean Sea near Cuba and Hispaniola, then follows the northeastern coast of South America over Venezuela and the Amazon basin. The vast green canopy of the Amazon rainforest is visible for several hours in the mid-flight section, with the broad brown Amazon River and its tributaries occasionally visible through breaks in cloud cover. The route then crosses into central Brazil's cerrado savanna before descending toward São Paulo.