Sit on the Right side of the plane for the best views on flights from Chicago to Oakland. While the left side offers good views during Chicago departure, the right side dominates the flight overall. The westbound route crosses the Midwest plains (relatively featureless), but the final descent into Oakland on the right side showcases the San Francisco Bay, Oakland Hills, and surrounding geography. Right-seat passengers get the most dramatic and geographically distinctive scenery during the approach and landing.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. Left side offers views of Lake Michigan immediately after departure, with the Chicago skyline visible to the south. The aircraft climbs westward over the lake before turning toward the Pacific, giving left-seat passengers a clear view of the water and urban landscape during the initial climb. Notable sights include: Lake Michigan, Chicago downtown skyline, Des Plaines River valley, suburban sprawl extending west toward Schaumburg.

When landing at Metropolitan Oakland International (OAK), sit on the Right side for the best views. Right side provides excellent views during the descent into Oakland. The aircraft approaches from the east over the Central Valley, and right-seat passengers see the San Francisco Bay, the Oakland Hills, and the bay shoreline as the plane descends toward the runway. The Sierra Nevada foothills are also visible to the east before the final approach turn. Notable sights include: San Francisco Bay, Oakland Hills, Mount Diablo (distant), Alameda Island and Oakland waterfront.

The flight from Chicago Ohare International (ORD) to Metropolitan Oakland International (OAK) takes Approximately 4 hours 45 minutes to 5 hours 15 minutes.

The flight path crosses Iowa and Nebraska (flat agricultural plains with occasional river valleys), then enters Colorado and Wyoming where the Rocky Mountains appear on the horizon to the north. The Great Basin of Nevada and Utah presents vast, arid terrain with scattered mountain ranges. As the aircraft approaches California, the Sierra Nevada becomes visible to the north and east. The Central Valley of California—a vast agricultural plain—dominates the final 90 minutes before descent into the Bay Area.