Sit on the Left side of the plane for the best views on flights from San Juan to Chicago. Left side wins at both ends of the flight. Departure gives you San Juan's lagoons and Old San Juan, and arrival gives you the Chicago skyline and Lake Michigan on approach. The left seat is the clear choice for this route.

During takeoff from Luis Munoz Marin International (SJU), sit on the Left side for the best views. SJU typically departs runway 8 heading east, then turns northwest. A left seat gives you the view back over San Juan's lagoons, the historic Old San Juan peninsula, and the Atlantic coastline as the aircraft banks north. You'll see the full sweep of the metropolitan area and Condado beach strip clearly. Notable sights include: Old San Juan peninsula, Condado Lagoon, Isla Verde beach strip, San Juan Bay.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. ORD typically lands on runways 10L/10C from the west, meaning the approach comes in from the west heading east. A left seat on final approach gives you the south side view over the Chicago grid, the downtown skyline to the southeast, and Lake Michigan beyond. The city layout is dramatically visible on a clear day. Notable sights include: Chicago downtown skyline, Lake Michigan shoreline, O'Hare suburban grid, Des Plaines River corridor.

The flight from Luis Munoz Marin International (SJU) to Chicago Ohare International (ORD) takes Approximately 3 hours 30 minutes to 4 hours.

After leaving Puerto Rico the route crosses the open Atlantic briefly before passing over Hispaniola and Cuba if routing southwest, or more commonly tracks northwest over the Bahamas chain — low flat islands and vivid shallow-water banks visible on clear days. The flight then crosses the Florida Straits and the Florida peninsula, where the flat green Everglades and Lake Okeechobee are visible. Continuing north over Georgia and Tennessee, the Appalachian ridgelines appear as parallel corrugated folds. Over Kentucky and Indiana the terrain flattens into the agricultural Midwest grid before descending into Chicago.