Sit on the Right side of the plane for the best views on flights from Chicago to San Jose. The right side delivers the more dramatic single moment of the flight — the volcanic Central Valley approach into SJO is genuinely spectacular. During cruise the right side also faces west over the Gulf of Mexico and eventually the Pacific coast of Central America, offering coastline views. Left side has the better Chicago departure, but the Costa Rica arrival on the right is the highlight of the journey.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare predominantly uses east-facing runways (10L/10R/9L/9R) for departures in westerly winds, meaning a left-side seat faces north toward the Chicago skyline and Lake Michigan shoreline. You get a clear view of the downtown Loop skyline and the lakefront as the aircraft climbs and turns south. Right side faces west into suburban sprawl with little of interest. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Navy Pier, Wrigley Field neighborhood.

When landing at Juan Santamaria International (SJO), sit on the Right side for the best views. Arrivals into SJO typically approach from the northwest on runway 07, meaning the aircraft tracks over the Central Valley from the northwest. The right side faces south toward the Talamanca mountain range and Irazú and Turrialba volcanoes. Left side looks north toward lower terrain and the Caribbean lowlands with less dramatic scenery. Notable sights include: Irazú Volcano, Turrialba Volcano, Central Valley of Costa Rica, San José urban area.

The flight from Chicago Ohare International (ORD) to Juan Santamaria International (SJO) takes Approximately 5 hours 30 minutes to 6 hours.

The flight tracks south-southeast over Illinois and Missouri, then crosses the Gulf of Mexico — a long overwater segment with no landmarks. The Yucatán Peninsula of Mexico appears as a flat green landmass. The aircraft then crosses Belize and Guatemala, where the Sierra de los Cuchumatanes and volcanic highlands of Guatemala become visible, including the chain of Guatemalan volcanoes near the Pacific coast. The flight descends over Nicaragua's Lake Nicaragua before entering Costa Rican airspace.