Right-side seats offer superior views on both legs: Lake Michigan shoreline during departure and the approach to Milwaukee. The 85-mile flight path runs roughly north-northwest, keeping Lake Michigan visible on the right throughout most of the journey.
Flown MDW to MKE? Did we get it right?
Flight Path
Chicago to Milwaukee is 81 miles (130 km), a flight of about 25 minutes.
Lake Michigan dominates the entire flight path; the aircraft maintains visual contact with the lake's eastern shoreline throughout. Racine, Wisconsin appears on the shoreline midway through the flight. The flight corridor passes over or near the lake for the entire journey, with suburban and industrial areas visible inland to the west.
Great circle distance and headings ›Phase by phase

Takeoff from MDW
RIGHTRight-side seats offer views of Lake Michigan's shoreline immediately after departure. The aircraft climbs northwestward from Midway, and right-side windows capture the lake's eastern edge and the Chicago lakefront as it recedes below.
Landing at MKE
LEFTLeft-side seats provide views of Lake Michigan and the Milwaukee shoreline during final approach. The aircraft descends from the southeast toward General Mitchell, and left windows capture the lake's western shore and Milwaukee's downtown area against the water.
Will your flight be in sunlight?
Pick a date and time in the Sun Map to watch the sun move across your whole flight.
About This Route
Which side of the plane should I sit on flying from Chicago Midway International (MDW) to General Mitchell International (MKE)?
Sit on the Right side of the plane for the best views on flights from Chicago to Milwaukee. Right-side seats offer superior views on both legs: Lake Michigan shoreline during departure and the approach to Milwaukee. The 85-mile flight path runs roughly north-northwest, keeping Lake Michigan visible on the right throughout most of the journey.
What can I see during takeoff from Chicago Midway International in Chicago?
During takeoff from Chicago Midway International (MDW), sit on the Right side for the best views. Right-side seats offer views of Lake Michigan's shoreline immediately after departure. The aircraft climbs northwestward from Midway, and right-side windows capture the lake's eastern edge and the Chicago lakefront as it recedes below. Notable sights include: Lake Michigan (eastern shoreline), Chicago downtown skyline (south and southeast during initial climb), Calumet River and industrial areas (southwest), residential neighborhoods of Chicago's south side.
What can I see when landing at General Mitchell International in Milwaukee?
When landing at General Mitchell International (MKE), sit on the Left side for the best views. Left-side seats provide views of Lake Michigan and the Milwaukee shoreline during final approach. The aircraft descends from the southeast toward General Mitchell, and left windows capture the lake's western shore and Milwaukee's downtown area against the water. Notable sights include: Lake Michigan (western shoreline and open water), Milwaukee downtown and harbor area, Kinnickinnic River mouth, residential neighborhoods north of downtown Milwaukee.
How long is the flight from Chicago to Milwaukee?
The flight from Chicago Midway International (MDW) to General Mitchell International (MKE) takes about 25 minutes. The shortest flight path between them is 81 miles (130 km); winds and air traffic control usually add a few percent.
What does the Chicago to Milwaukee flight path pass over?
Lake Michigan dominates the entire flight path; the aircraft maintains visual contact with the lake's eastern shoreline throughout. Racine, Wisconsin appears on the shoreline midway through the flight. The flight corridor passes over or near the lake for the entire journey, with suburban and industrial areas visible inland to the west.