Sit on the Left side of the plane for the best views on flights from Milwaukee to Chicago. The left side wins both ends of this short flight. At takeoff you get Lake Michigan and the Milwaukee lakefront, and on descent you get the best angle toward the Chicago metro. The flight is so brief — roughly 20-25 minutes — that there is almost no cruise phase, so takeoff and landing views are essentially the entire experience.

During takeoff from General Mitchell International (MKE), sit on the Left side for the best views. MKE's primary departure runway 01R sends aircraft northward before turning south toward Chicago, but the dominant departure for southbound flights is runway 19L heading south. On a southbound departure, the left (east) side gives you Lake Michigan immediately off the wing — a massive, flat expanse of blue-gray water that fills the view. The Milwaukee lakefront, downtown skyline, and harbor are clearly visible before the aircraft turns toward Chicago. Notable sights include: Lake Michigan shoreline, Milwaukee downtown skyline and lakefront, Milwaukee Harbor and Jones Island water treatment facility, Calatrava-winged Milwaukee Art Museum (visible as a white structure on the lakefront).

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. ORD arrivals from the north typically use runways 10L/10C/10R (heading east) or 27L/27R (heading west). On a northbound arrival from Milwaukee, aircraft often approach from the north on runways oriented east-west. The left (south) side on a westbound approach gives you Chicago's northern suburbs and a distant view of the downtown skyline to the southeast. On an eastbound approach, the left side faces north toward the suburbs. Either way, the left seat catches the city more consistently as the aircraft descends over the northwest Chicago metro. Notable sights include: Chicago O'Hare airport complex and runways visible below on final, northwest Chicago suburban grid, distant Chicago downtown skyline (Willis Tower and John Hancock visible on clear days to the southeast), Interstate 90/94 corridor cutting through the suburban landscape.

The flight from General Mitchell International (MKE) to Chicago Ohare International (ORD) takes Approximately 20-30 minutes gate to gate, with very little level cruise time.

The flight path runs almost due south along the Illinois-Wisconsin border corridor. Lake Michigan is visible to the left (east) for much of the flight at low altitude. The terrain is entirely flat glaciated farmland and suburban sprawl. Waukegan and North Chicago are visible below as the aircraft passes over Lake County, Illinois. No significant topographic features — this is one of the flattest flight corridors in the continental US.