Sit on the Left side of the plane for the best views on flights from Chicago to San Francisco. Left side wins both the departure and arrival. During the flight itself, the left side also faces generally south-southwest, giving better views of the Sierra Nevada as you cross into California, particularly the high peaks of the central Sierra visible on the left horizon.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. ORD departures heading west or southwest on runways 10L/10C/10R put the Chicago skyline and Lake Michigan on the left side during the initial climb and turn. You get a clear view of the downtown Loop, Grant Park, and the lakefront stretching north and south. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Grant Park and Museum Campus, Midway Airport to the south.

When landing at San Francisco International (SFO), sit on the Left side for the best views. SFO sits on the west shore of San Francisco Bay, and most arrivals come in from the east or southeast over the Bay. A left-side seat gives you the best view of the Bay, the San Francisco Peninsula, and the city itself during the approach. Right side faces east toward the East Bay hills. Notable sights include: San Francisco Bay, San Francisco Peninsula and city skyline, Golden Gate Bridge (distant), San Mateo-Hayward Bridge.

The flight from Chicago Ohare International (ORD) to San Francisco International (SFO) takes Approximately 4 hours 15 minutes to 4 hours 45 minutes westbound.

The route crosses the Mississippi River near the Iowa-Illinois border, then the flat agricultural plains of Iowa and Nebraska, the Rocky Mountains of southern Wyoming or northern Colorado (depending on routing), the Great Salt Lake visible to the south in Utah, the Nevada Basin and Range desert, and finally the Sierra Nevada before descending into the Central Valley of California and crossing the Diablo Range into the Bay Area.