Sit on the Left side of the plane for the best views on flights from Oranjestad to Chicago. Left side wins both the departure over Aruba's leeward coast and Oranjestad, and the arrival with the Chicago skyline and Lake Michigan. Over the Caribbean and Gulf of Mexico the views are largely ocean on both sides, but the left side bookends the flight with the two most visually rewarding moments.

During takeoff from Reina Beatrix International (AUA), sit on the Left side for the best views. Aruba's main runway 11/29 means departures heading northwest toward the US will initially climb out over the island's western end and the Caribbean. Left side gives you the best view of Oranjestad harbor, the salt flats near Bubali, and the turquoise waters of the leeward coast. Right side faces the open Atlantic and is largely featureless ocean. Notable sights include: Oranjestad harbor and downtown, Bubali salt ponds and flamingo sanctuary, the leeward coastline and reef line visible through shallow water color changes, Eagle Beach and Palm Beach hotel strip.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare's primary arrival runways from the south and southeast (runways 10L/10R or 28L/28R depending on wind) typically bring aircraft over the southern Chicago suburbs and then the city grid. Left side on approach from the southeast gives a clear view of the Chicago downtown skyline, Lake Michigan shoreline, and the lakefront parks. Right side faces the flat western suburbs with little of visual interest. Notable sights include: Chicago downtown skyline including Willis Tower and the Loop, Lake Michigan shoreline and lakefront, Grant Park and the Museum Campus peninsula, the dense grid of Chicago's South and West Side neighborhoods.

The flight from Reina Beatrix International (AUA) to Chicago Ohare International (ORD) takes Approximately 4 hours 45 minutes to 5 hours 15 minutes.

After leaving Aruba the route crosses the southern Caribbean Sea, then passes over the Yucatan Channel between Cuba and Mexico's Yucatan Peninsula. The flight then crosses the Gulf of Mexico — largely featureless open water for roughly an hour — before making landfall near the Louisiana or Mississippi coast. From there the route tracks northeast over the Mississippi River valley, crossing the Ohio River valley and the flat agricultural plains of Indiana before descending into Chicago.