Sit on the Left side of the plane for the best views on flights from Orlando to Chicago. While takeoff favors the right for local Orlando views, the landing approach to Chicago from the northeast provides superior geography on the left side, including Lake Michigan and the city's distinctive shoreline. The left seat wins the overall flight.

During takeoff from Orlando International (MCO), sit on the Right side for the best views. Right side captures the Atlantic coastal approach and the immediate Orlando metro area as you climb northwestward. MCO typically departs runways 17L/R or 18L/R heading north-northwest, so the right wing shows the city's sprawl and the transition from developed areas to central Florida's lakes and wetlands. Notable sights include: Orlando downtown skyline (small but visible), Lake Apopka to the northwest, Shingle Creek watershed and chain of lakes extending north, Atlantic coastal plain terrain.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. Left side provides the best views during approach to MDW. Chicago Midway typically uses runways 31L/R or 04L/R depending on wind. On descent from the northeast, the left wing shows Lake Michigan's shoreline, downtown Chicago's skyline, and the Illinois prairie landscape. Even on westerly approaches, the left side captures more of the city's distinctive geography. Notable sights include: Lake Michigan shoreline and harbor areas, Chicago downtown skyline (Willis Tower and clustered high-rises visible as a distinct cluster), the Illinois prairie and suburban grid extending westward, Des Plaines River valley.

The flight from Orlando International (MCO) to Chicago Midway International (MDW) takes Approximately 3 hours 15 minutes.

The flight path crosses central Georgia (Chattahoochee River valley visible around 1 hour out), then Tennessee's Cumberland Plateau region, followed by Kentucky's Bluegrass region and Ohio River valley. Around the 2-hour mark, the Ohio River becomes visible as a distinct meandering line. The flight then crosses Indiana's agricultural landscape—a patchwork of rectangular crop fields—before approaching the Chicago metropolitan area. No major mountain ranges are visible; the Appalachian foothills remain too far east. The terrain is predominantly rolling to flat throughout, with rivers and lakes providing the most distinctive linear features.