Sit on the Right side of the plane for the best views on flights from Chicago to San Francisco. The right side wins overall. The Chicago departure view of the skyline and Lake Michigan is genuinely spectacular and hard to beat. Across the flight, the right side also faces generally south, giving better views of the Sierra Nevada as you cross into California, with peaks like the central Sierra visible on the horizon before descent.

During takeoff from Chicago Midway International (MDW), sit on the Right side for the best views. MDW typically departs runway 31L/31C heading northwest, which puts the right side facing northeast toward downtown Chicago. You get a clear view of the Loop skyline, Lake Michigan, and the lakefront as the plane banks westward. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Grant Park and Museum Campus, Chicago River corridor.

When landing at San Francisco International (SFO), sit on the Left side for the best views. SFO primarily uses runways 28L/28R for arrivals, with aircraft approaching from the east over the Bay. The left side faces south and gives you the best view of the San Francisco Bay, the San Mateo Bridge, and the Peninsula as you descend over the water. Notable sights include: San Francisco Bay, San Mateo Bridge, Peninsula cities along US-101, Santa Cruz Mountains to the south.

The flight from Chicago Midway International (MDW) to San Francisco International (SFO) takes Approximately 4 hours to 4 hours 30 minutes.

The flight crosses the Mississippi River over Iowa, then the flat agricultural plains of Nebraska and Iowa give way to the Rocky Mountains in Colorado and Wyoming visible to the south. Over Utah, the Great Salt Lake may be visible to the right. The Sierra Nevada range is crossed near the California-Nevada border, with the high peaks of the central Sierra visible before descent into the Bay Area.