Sit on the Right side of the plane for the best views on flights from Chicago to Detroit. The right side delivers the more dramatic and iconic view at takeoff — the Chicago skyline and Lake Michigan shoreline are genuinely spectacular. The landing left-side view over the Detroit River is good but the city is smaller and less visually striking. Right side wins overall for the Chicago departure alone.

During takeoff from Chicago Ohare International (ORD), sit on the Right side for the best views. ORD's most common eastbound departures use runways 10R/10L or 9R/9L, heading roughly east. The right side faces south, giving views over the Chicago metropolitan grid, the lakefront, and downtown Chicago's skyline as the aircraft climbs and turns east. The left side faces north toward suburban sprawl with fewer distinctive features. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), Lake Michigan shoreline, Chicago River grid pattern, O'Hare suburban sprawl contrast.

When landing at Detroit Metro Wayne Co (DTW), sit on the Left side for the best views. DTW sits southwest of Detroit, and aircraft typically approach from the west on runways 21L/21R or from the northwest on 27L/27R. On a westerly approach, the left side faces south and southeast, giving views over the Detroit River, Windsor Ontario across the border, and the Detroit downtown skyline. The right side faces north toward flat Michigan farmland. Notable sights include: Detroit River and US-Canada border, Windsor Ontario across the river, Detroit downtown skyline, Lake St. Clair to the northeast.

The flight from Chicago Ohare International (ORD) to Detroit Metro Wayne Co (DTW) takes Approximately 45 to 55 minutes.

The flight crosses flat northern Indiana and southern Michigan — largely agricultural land with small lakes scattered across glacially-formed terrain. The Kalamazoo and Battle Creek areas pass to the south. Lake Michigan is briefly visible to the north early in the flight. The terrain is uniformly flat with no significant elevation changes, typical of the Great Lakes glacial plain.