The right side offers the only real visual interest on this short, flat-terrain hop — a glimpse of Madison's lakes on departure and a distant look at Chicago's skyline and Lake Michigan on arrival, whereas the left side stays over featureless farmland and suburbs the whole way.
Flight Path
Flat agricultural plains of southern Wisconsin and northern Illinois, dotted with small towns, rivers, and grain silos; no major terrain features at cruise altitude.
Great circle distance and headings ›Phase by phase
Takeoff from MSN
RIGHTDeparting MSN to the south, the right (west-facing) side gives a brief but clear view of Lake Mendota's shoreline and Madison's isthmus skyline just after liftoff, before the flat farmland of southern Wisconsin takes over. The left side mostly shows open fields with little to distinguish it.

Landing at ORD
RIGHTOn approach into ORD from the northwest, the right side can catch a distant glimpse of the Chicago skyline and a sliver of Lake Michigan before the turn onto final, while the left side faces featureless suburban sprawl and flat Illinois terrain.
Landmarks on this routeAll landmarks →
Will your flight be in sunlight?
See exactly which side of the plane gets sun and shade at your departure time.
About This Route
Which side of the plane should I sit on flying from Dane Co Rgnl Truax Fld (MSN) to Chicago Ohare International (ORD)?
Sit on the Right side of the plane for the best views on flights from Madison to Chicago. The right side offers the only real visual interest on this short, flat-terrain hop — a glimpse of Madison's lakes on departure and a distant look at Chicago's skyline and Lake Michigan on arrival, whereas the left side stays over featureless farmland and suburbs the whole way.
What can I see during takeoff from Dane Co Rgnl Truax Fld in Madison?
During takeoff from Dane Co Rgnl Truax Fld (MSN), sit on the Right side for the best views. Departing MSN to the south, the right (west-facing) side gives a brief but clear view of Lake Mendota's shoreline and Madison's isthmus skyline just after liftoff, before the flat farmland of southern Wisconsin takes over. The left side mostly shows open fields with little to distinguish it. Notable sights include: Lake Mendota, Madison isthmus skyline, University of Wisconsin campus area.
What can I see when landing at Chicago Ohare International in Chicago?
When landing at Chicago Ohare International (ORD), sit on the Right side for the best views. On approach into ORD from the northwest, the right side can catch a distant glimpse of the Chicago skyline and a sliver of Lake Michigan before the turn onto final, while the left side faces featureless suburban sprawl and flat Illinois terrain. Notable sights include: Distant Chicago skyline, Lake Michigan shoreline, O'Hare's runway complex.
How long is the flight from Madison to Chicago?
The flight from Dane Co Rgnl Truax Fld (MSN) to Chicago Ohare International (ORD) takes 0h 45m.
What does the Madison to Chicago flight path pass over?
Flat agricultural plains of southern Wisconsin and northern Illinois, dotted with small towns, rivers, and grain silos; no major terrain features at cruise altitude.