Sit on the Right side of the plane for the best views on flights from Chicago to Liberia. While left side wins at takeoff for the Chicago skyline, the right side delivers more sustained geographic interest over the Gulf of Mexico crossing and the dramatic Costa Rican volcanic landscape on arrival. The Guanacaste volcanoes on approach are genuinely spectacular and right side captures them on the most common landing configuration.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare's primary departure runways (10L/10R heading east, or 28L/28R heading west) mean left-side seats get Chicago's downtown skyline. Departing eastbound on 10s, the left side faces north toward the city grid and Lake Michigan's shoreline. Departing westbound on 28s, left side looks south over the dense suburban sprawl toward the city center. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), Lake Michigan shoreline, Chicago River corridor, O'Hare's distinctive runway complex below.

When landing at Daniel Oduber Quiros International (LIR), sit on the Right side for the best views. LIR's primary runway is 07/25. Landing on runway 07 (heading northeast), right-side seats face southeast toward the Guanacaste volcanic range including Volcán Rincón de la Vieja and Volcán Miravalles on approach. Landing on runway 25 (heading southwest), right side faces northwest over the Gulf of Papagayo and Pacific coastline of Guanacaste. Notable sights include: Volcán Rincón de la Vieja (1,916m), Volcán Miravalles, Gulf of Papagayo coastline, Guanacaste dry forest lowlands.

The flight from Chicago Ohare International (ORD) to Daniel Oduber Quiros International (LIR) takes Approximately 5 hours 15 minutes to 5 hours 45 minutes.

The flight tracks south-southwest over Missouri and Arkansas, then crosses the Gulf of Mexico — a long overwater segment with little to see. The Yucatan Peninsula of Mexico appears as a flat, jungle-covered landmass. The flight then crosses over Belize and Guatemala before entering Costa Rican airspace, where the Central American cordillera becomes visible with volcanic peaks along the spine of the isthmus.