Sit on the Left side of the plane for the best views on flights from Detroit to Chicago. While takeoff favors the right for Detroit River views, the landing approach on the left side is more visually rewarding and offers sustained views of Chicago's urban geography. Left side captures the approach corridor over the Des Plaines River and Chicago neighborhoods, making it the better overall choice for this route.

During takeoff from Detroit Metro Wayne Co (DTW), sit on the Right side for the best views. Right side captures the Detroit River and Windsor, Ontario immediately after departure. DTW typically departs runways 03L/03R or 21L/21R; westbound departures on 03R give the clearest view of the river corridor and Lake St. Clair to the northeast before the aircraft turns southwest toward Chicago. Notable sights include: Detroit River (flowing north-south between Detroit and Windsor), Lake St. Clair (large freshwater lake northeast of Detroit), Windsor skyline across the international border, suburban Detroit sprawl extending west.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. Left side provides the best approach views into Midway. Typical landing runways are 04L/04R or 22L/22R; eastbound approaches on 04L/04R descend over the Chicago Lawn and Marquette neighborhoods, giving left-seat passengers clear views of the city grid, the Des Plaines River, and industrial areas immediately west of the airport. Notable sights include: Des Plaines River (flowing south through Chicago's southwest side), Chicago street grid and residential neighborhoods (Chicago Lawn, Marquette districts), industrial and rail yards west of Midway, Midway Airport runways and taxiways.

The flight from Detroit Metro Wayne Co (DTW) to Chicago Midway International (MDW) takes Approximately 45-50 minutes.

The flight path crosses southwestern Michigan and northwestern Indiana. Notable features include the Kalamazoo River valley (visible around 20 minutes into flight), scattered lakes in southern Michigan, and the transition from agricultural land to suburban sprawl as the aircraft approaches the Chicago metropolitan area. Lake Michigan remains visible to the north throughout much of the flight but is not directly on the westbound routing.