Sit on the Left side of the plane for the best views on flights from San Francisco to Chicago. The left seat wins at both ends of the flight. Departure gives you San Francisco Bay and the city skyline, and arrival gives you the Chicago lakefront and downtown. Over the Rockies and Great Plains the views are similar on both sides, so the left seat's advantage at departure and landing makes it the clear overall choice.

During takeoff from San Francisco International (SFO), sit on the Left side for the best views. SFO typically departs westward over the Bay on runways 28L/28R, then turns northeast toward Chicago. A left/north-facing seat captures San Francisco Bay, the city skyline, and the Bay Bridge as you climb out. The right side faces south toward the Peninsula with less dramatic scenery. Notable sights include: San Francisco Bay, Bay Bridge, San Francisco skyline, Marin Headlands.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. ORD typically lands from the east on runways 10L/10R or from the northwest on 27L/27R depending on winds. On the common eastward approach, a left seat faces south over the Chicago lakefront, giving clear views of Lake Michigan shoreline, Grant Park, and the downtown skyline. The right seat faces north toward suburban sprawl with fewer landmarks. Notable sights include: Lake Michigan shoreline, Chicago downtown skyline, Grant Park, Wrigley Building area.

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

The flight crosses the Sierra Nevada (visible as a snow-capped range climbing out of California), then the Great Basin desert of Nevada and Utah with its dry lake beds and basin-and-range topography, the Wasatch Front near Salt Lake City, the Rocky Mountains of Colorado and Wyoming visible as a broad elevated mass, then the flat agricultural checkerboard of Nebraska, Iowa, and Illinois all the way into Chicago