Sit on the Left side of the plane for the best views on flights from Kahului to Chicago. Left side wins both ends of the flight. At takeoff you get the dramatic Maui volcanic landscape and inter-island channel views, and at landing you get the full Chicago lakefront and skyline panorama. The right side offers ocean on departure and suburban sprawl on arrival — neither as visually compelling.

During takeoff from Kahului (OGG), sit on the Left side for the best views. Departing Kahului on runway 02 (northward), the left/west side gives you a clear look at the West Maui Mountains and the isthmus connecting them to Haleakala. As the plane banks northeast toward the mainland, the left side also captures the channel views toward Molokai and Lanai. Notable sights include: Haleakala volcano (east Maui), West Maui Mountains, Maalaea Bay, Molokai across the Pailolo Channel.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. Approaching O'Hare typically from the east or southeast on runways oriented roughly east-west, the left/south side gives views over the Chicago lakefront, Grant Park, the Loop skyline, and Lake Michigan's shoreline. The right side faces northwest toward suburban sprawl with fewer distinctive features. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Grant Park and Museum Campus, Wrigley Field area in Lincoln Park.

The flight from Kahului (OGG) to Chicago Ohare International (ORD) takes Approximately 8 to 8.5 hours.

The flight tracks northeast over the open Pacific for the first few hours with no land visible. The California coast appears roughly over the Central Valley or Sierra Nevada foothills depending on routing. The route then crosses the Great Basin desert, the Rocky Mountains (visible as a broad corrugated range), the Colorado Plateau, and the flat agricultural plains of Iowa and Illinois before descending into Chicago.