Sit on the Right side of the plane for the best views on flights from Chicago to Milwaukee. This is an extremely short flight — barely 10 minutes of cruise at altitude. The landing approach into MKE on the right side delivers the most concentrated and visually rewarding single view: Lake Michigan up close with Milwaukee's harbor and downtown in one frame. The takeoff left-side view is good but the Chicago skyline is distant and partially obscured by haze at this angle.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. Departing ORD, aircraft typically use runways oriented east-west or northwest-southeast. On a northbound departure toward MKE, the left (west) side gives you a clear view back over the Chicago suburbs and the beginning of Lake Michigan's shoreline curving northward. The right side faces inland toward flat Illinois farmland with little of interest. Notable sights include: Lake Michigan shoreline curving north, Chicago's dense suburban grid of O'Hare area, Des Plaines River corridor, and the distant downtown Chicago skyline to the southeast.

When landing at General Mitchell International (MKE), sit on the Right side for the best views. MKE's primary runways run roughly north-south. On approach from the south, aircraft typically come in from over the lake or parallel to the shoreline. The right (east) side gives a direct view of Lake Michigan and Milwaukee's lakefront, including the harbor and downtown waterfront. The left side faces inland over flat Wisconsin suburbs. Notable sights include: Lake Michigan's western shoreline, Milwaukee's downtown lakefront and harbor, Milwaukee River mouth at the lake, and the visible grid of Milwaukee's downtown street pattern.

The flight from Chicago Ohare International (ORD) to General Mitchell International (MKE) takes Approximately 25-35 minutes gate to gate, with only 8-12 minutes at cruise altitude.

The flight tracks almost due north along the Illinois-Wisconsin border corridor. The dominant feature throughout is Lake Michigan to the east, visible as a vast dark blue expanse. Below, the landscape is flat glaciated terrain with the suburban sprawl of Kenosha and Racine visible along the lakeshore midway through the route. Interstate 94 is traceable as a straight corridor running parallel to the flight path.