Sit on the Left side of the plane for the best views on flights from Detroit to Chicago. Left side delivers the best views at both ends of this short flight — Detroit River and skyline on departure, Chicago lakefront and skyline on approach. The right side sees mostly flat Indiana and Illinois farmland throughout.

During takeoff from Detroit City (DET), sit on the Left side for the best views. Detroit City Airport typically departs runway 33 (heading northwest), putting the left side facing southwest toward downtown Detroit and the Detroit River. You get a clear view of the Detroit skyline, the river, and Windsor, Ontario across the border. Notable sights include: Downtown Detroit skyline, Detroit River, Windsor Ontario waterfront, Belle Isle Park in the river.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare arrivals on runway 10L/10R (heading east) or 28L/28R vary, but the dominant westerly approach puts the left side facing south toward the Chicago skyline along Lake Michigan. The left seat gets the iconic lakefront view as you descend over the northern suburbs. Notable sights include: Chicago downtown skyline along Lake Michigan, Lake Michigan shoreline, Evanston and northern suburban grid, O'Hare airport sprawl.

The flight from Detroit City (DET) to Chicago Ohare International (ORD) takes Approximately 45-55 minutes.

The flight crosses southern Michigan farmland, then the Indiana state line near South Bend, passing over flat agricultural terrain of northern Indiana and Illinois. Lake Michigan is not directly on the route but may be visible to the left (north) in the middle portion of the flight as a distant blue horizon. No significant terrain changes — this is uniformly flat Great Lakes lowland throughout.