Sit on the Left side of the plane for the best views on flights from San Jose to Chicago. Left side wins at both ends of the flight. At departure you get San Francisco Bay and the Diablo Range; at arrival you get the Chicago skyline and Lake Michigan. The mid-flight view over the Sierra Nevada and Rockies is roughly equal on both sides, so the departure and arrival advantages make left the clear overall choice.

During takeoff from Norman Y Mineta San Jose International (SJC), sit on the Left side for the best views. SJC departures on runway 30R/30L head northwest, then aircraft typically turn eastward. Left side gives you a clear view south over the Santa Clara Valley floor and the southern end of San Francisco Bay, with the Diablo Range rising behind it. You get the bay's salt evaporation ponds — vivid geometric patches of pink, orange, and green — before the aircraft climbs out over the hills. Notable sights include: San Francisco Bay salt evaporation ponds, Diablo Range foothills, Santa Clara Valley urban grid, Mount Hamilton (4,265 ft) to the southeast.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. ORD arrivals from the west typically use runways oriented east-west (runway 10 series), meaning the aircraft approaches from the west over the Chicago suburbs. Left side gives you the best view of the Chicago skyline to the south as you descend, with Lake Michigan's western shoreline and the downtown towers clearly visible on approach. The right side faces north toward less distinctive suburban sprawl. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), Lake Michigan western shoreline, suburban Cook County grid, O'Hare airport layout visible just before touchdown.

The flight from Norman Y Mineta San Jose International (SJC) to Chicago Ohare International (ORD) takes Approximately 4 hours to 4 hours 30 minutes.

After climbing out of the Bay Area, the route crosses the Sierra Nevada (visible as a major snow-capped range in winter/spring), then the Great Basin desert of Nevada and Utah — flat, arid, with salt flats visible near the Utah border. The Wasatch Range near Salt Lake City is a notable landmark. The route then crosses the Rocky Mountains over Colorado or Wyoming depending on routing, followed by the high plains of Nebraska and Iowa — flat agricultural grid with the Platte River valley visible — before descending into the Chicago metro area.