The Chicago skyline and Lake Michigan glimpse during departure offer more visual drama and a genuine urban-coastal contrast than anything on the right side, even though the Nashville approach adds some interest late in the flight.
Flown MDW to BNA? Did we get it right?
Flight Path
Chicago to Nashville is 395 miles (636 km), a flight of about 1 hour 25 minutes.
Flat agricultural plains of northern Illinois and southern Indiana, with the Ohio River valley and rolling hills of western Kentucky visible as the route crosses into Tennessee.
Great circle distance and headings ›Phase by phase

Takeoff from MDW
LEFTDeparting Midway to the south, passengers on the left (east) side get a brief but clear view of the Chicago skyline and Lake Michigan's shoreline as the aircraft climbs out before turning onto its southbound course. This is the only real visual highlight of an otherwise flat-terrain route.

Landing at BNA
RIGHTOn approach into BNA from the north, the aircraft typically lines up for the south-facing runways, putting downtown Nashville and the Cumberland River's bends off to the right side during the final descent. It's a modest but genuine urban view compared to the featureless farmland on the left.
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About This Route
Which side of the plane should I sit on flying from Chicago Midway International (MDW) to Nashville International (BNA)?
Sit on the Left side of the plane for the best views on flights from Chicago to Nashville. The Chicago skyline and Lake Michigan glimpse during departure offer more visual drama and a genuine urban-coastal contrast than anything on the right side, even though the Nashville approach adds some interest late in the flight.
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 Midway to the south, passengers on the left (east) side get a brief but clear view of the Chicago skyline and Lake Michigan's shoreline as the aircraft climbs out before turning onto its southbound course. This is the only real visual highlight of an otherwise flat-terrain route. Notable sights include: Chicago skyline (Willis Tower, Loop), Lake Michigan shoreline, Midway's grid of residential neighborhoods.
What can I see when landing at Nashville International in Nashville?
When landing at Nashville International (BNA), sit on the Right side for the best views. On approach into BNA from the north, the aircraft typically lines up for the south-facing runways, putting downtown Nashville and the Cumberland River's bends off to the right side during the final descent. It's a modest but genuine urban view compared to the featureless farmland on the left. Notable sights include: Downtown Nashville skyline, Cumberland River bends, rolling middle Tennessee farmland.
How long is the flight from Chicago to Nashville?
The flight from Chicago Midway International (MDW) to Nashville International (BNA) takes about 1 hour 25 minutes. The shortest flight path between them is 395 miles (636 km); winds and air traffic control usually add a few percent.
What does the Chicago to Nashville flight path pass over?
Flat agricultural plains of northern Illinois and southern Indiana, with the Ohio River valley and rolling hills of western Kentucky visible as the route crosses into Tennessee.