Sit on the Right side of the plane for the best views on flights from Sao Paulo to Chicago. While the São Paulo departure offers urban and escarpment scenery (2.5), the Chicago approach to Lake Michigan with the downtown skyline and vast water views scores higher (3.5). The landing sequence dominates the overall experience on this long transatlantic route, and the Lake Michigan approach is significantly more visually dramatic than the flat Illinois farmland on the left side during descent.

During takeoff from Congonhas (CGH), sit on the Left side for the best views. São Paulo's urban sprawl and the Serra da Mantiqueira escarpment to the northwest provide immediate visual interest during climb-out from Congonhas. The right side faces inland plateau with less dramatic terrain. Notable sights include: Serra da Mantiqueira ridge, São Paulo metropolitan sprawl, Pinheiros River valley, Atlantic coastal escarpment edge.

When landing at Chicago Ohare International (ORD), sit on the Right side for the best views. The approach to Chicago from the south-southwest crosses the southern shore of Lake Michigan, revealing the dramatic urban waterfront, downtown skyline, and the lake's vast expanse. The left side would show flat Illinois farmland with minimal visual interest. Notable sights include: Lake Michigan shoreline, Chicago downtown skyline and Willis Tower, Grant Park lakefront, Indiana Dunes to the southeast.

The flight from Congonhas (CGH) to Chicago Ohare International (ORD) takes 9h 15m.

The flight crosses the Caribbean Sea (minimal landmarks), then the Yucatan Peninsula and Gulf of Mexico coast near the Mexico-Texas border, followed by the Mississippi River valley, and finally the Great Lakes region. Most of the cruise is over open water or flat terrain with limited scenic value.