Sit on the Right side of the plane for the best views on flights from Chicago to Chicago. This is an extremely short flight — under 20 minutes — and the aircraft rarely climbs above 10,000 feet. The right side captures the Chicago Loop skyline and Lake Michigan during the climb out of ORD, which is the most visually dramatic moment of this brief hop. The landing view from the left is good but the takeoff right-side view of the city skyline is the highlight.

During takeoff from Chicago Ohare International (ORD), sit on the Right side for the best views. Departing ORD, aircraft typically use runways oriented east-west or northwest-southeast. On an eastbound or southeastbound departure toward MDW, the right side faces south toward the Chicago skyline. The Loop's skyscrapers, Lake Michigan's shoreline, and the dense urban grid of Chicago's North Side are clearly visible on the right. Notable sights include: Chicago Loop skyline, Lake Michigan western shoreline, O'Hare suburban grid of Schiller Park and Rosemont, I-294 Tri-State Tollway corridor.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. MDW is typically approached from the northeast or east, meaning the aircraft tracks southwest over the city. On final approach, the left side faces southeast toward the Chicago Loop and the lakefront, giving a direct view of the dense South Side neighborhoods, Midway's surrounding bungalow belt, and the downtown skyline receding behind. The right side faces northwest into featureless southwest suburban sprawl. Notable sights include: Chicago Loop skyline to the northeast, South Side bungalow belt grid, Midway Airport runway layout visible below, Dan Ryan Expressway corridor.

The flight from Chicago Ohare International (ORD) to Chicago Midway International (MDW) takes 15 to 20 minutes.

The entire flight crosses the continuous urban grid of Chicago. At cruise altitude of roughly 8,000 to 12,000 feet, you pass over the Northwest Side neighborhoods of Jefferson Park and Portage Park, then the West Side grid around Humboldt Park and Garfield Park. The flat Illinois prairie topography means no terrain features — the visual interest is entirely the urban fabric, expressway corridors like I-290, and the elevated rail lines of the CTA system.