Both sides are fairly flat and unremarkable for most of the cruise, but the right side wins narrowly due to the more distinct river and skyline views on approach into MSP, giving it a slight edge over the brief Chicago glimpse at takeoff.
Flight Path
Flat agricultural plains of northern Illinois and southern Wisconsin, with the Wisconsin River valley and rolling farmland visible below during cruise.
Great circle distance and headings ›Phase by phase

Takeoff from MDW
LEFTDeparting MDW to the north, the left side offers a brief glimpse of downtown Chicago's skyline and Lake Michigan's shoreline before the route turns inland. It's a short window of urban scenery in an otherwise flat-terrain flight.

Landing at MSP
RIGHTOn approach into MSP, the right side gives a good view of the Mississippi River bends and the Minneapolis-St. Paul urban core, including the confluence area near downtown. This is one of the more scenic urban approach features on this short route.
Landmarks on this routeAll landmarks →
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About This Route
Which side of the plane should I sit on flying from Chicago Midway International (MDW) to Minneapolis St Paul International (MSP)?
Sit on the Right side of the plane for the best views on flights from Chicago to Minneapolis. Both sides are fairly flat and unremarkable for most of the cruise, but the right side wins narrowly due to the more distinct river and skyline views on approach into MSP, giving it a slight edge over the brief Chicago glimpse at takeoff.
What can I see during takeoff from Chicago Midway International in Chicago?
During takeoff from Chicago Midway International (MDW), sit on the Left side for the best views. Departing MDW to the north, the left side offers a brief glimpse of downtown Chicago's skyline and Lake Michigan's shoreline before the route turns inland. It's a short window of urban scenery in an otherwise flat-terrain flight. Notable sights include: Chicago skyline (Willis Tower, Sears Tower area), Lake Michigan shoreline, Midway's surrounding grid neighborhoods.
What can I see when landing at Minneapolis St Paul International in Minneapolis?
When landing at Minneapolis St Paul International (MSP), sit on the Right side for the best views. On approach into MSP, the right side gives a good view of the Mississippi River bends and the Minneapolis-St. Paul urban core, including the confluence area near downtown. This is one of the more scenic urban approach features on this short route. Notable sights include: Mississippi River, downtown Minneapolis skyline, Minnehaha Creek area, Twin Cities lakes.
How long is the flight from Chicago to Minneapolis?
The flight from Chicago Midway International (MDW) to Minneapolis St Paul International (MSP) takes 1h 15m.
What does the Chicago to Minneapolis flight path pass over?
Flat agricultural plains of northern Illinois and southern Wisconsin, with the Wisconsin River valley and rolling farmland visible below during cruise.