New Orleans to Chicago is 838 miles (1,349 km), a flight of about 2 hours 15 minutes.
The right side bookends the flight with two strong scenic moments — Lake Pontchartrain and New Orleans at takeoff, Lake Michigan and the Chicago skyline at landing — while the cruise phase over Mississippi and Illinois farmland is largely flat regardless of side. The left side does catch stretches of the Mississippi River, but it's intermittent and less striking than the two urban/water bookends on the right.
Flight Path
The route crosses the Mississippi River valley near the Arkansas-Tennessee border, passing close to Memphis, then continues over flat farmland in the Missouri Bootheel and southern Illinois before approaching Chicago.
Great circle distance and headings ›Phase by phase

Takeoff from MSY
RIGHTDeparting MSY northbound, the initial turn passes over Lake Pontchartrain with New Orleans' downtown skyline and the Mississippi River's bend through the city visible off the right side. It's one of the few genuinely photogenic departure sequences on this route.

Landing at ORD
RIGHTArrivals into ORD from the south typically swing over the northern Chicago suburbs before lining up on the east-west runways, giving a clear view of Lake Michigan and the Chicago skyline off the right side during the turn onto final.
Landmarks on this routeAll landmarks →
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About This Route
Which side of the plane should I sit on flying from Louis Armstrong New Orleans International (MSY) to Chicago Ohare International (ORD)?
Sit on the Right side of the plane for the best views on flights from New Orleans to Chicago. The right side bookends the flight with two strong scenic moments — Lake Pontchartrain and New Orleans at takeoff, Lake Michigan and the Chicago skyline at landing — while the cruise phase over Mississippi and Illinois farmland is largely flat regardless of side. The left side does catch stretches of the Mississippi River, but it's intermittent and less striking than the two urban/water bookends on the right.
What can I see during takeoff from Louis Armstrong New Orleans International in New Orleans?
During takeoff from Louis Armstrong New Orleans International (MSY), sit on the Right side for the best views. Departing MSY northbound, the initial turn passes over Lake Pontchartrain with New Orleans' downtown skyline and the Mississippi River's bend through the city visible off the right side. It's one of the few genuinely photogenic departure sequences on this route. Notable sights include: Lake Pontchartrain, New Orleans downtown skyline, Mississippi River bend, Lake Pontchartrain Causeway.
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. Arrivals into ORD from the south typically swing over the northern Chicago suburbs before lining up on the east-west runways, giving a clear view of Lake Michigan and the Chicago skyline off the right side during the turn onto final. Notable sights include: Chicago skyline, Lake Michigan shoreline, Chicago suburbs, O'Hare approach corridor.
How long is the flight from New Orleans to Chicago?
The flight from Louis Armstrong New Orleans International (MSY) to Chicago Ohare International (ORD) takes about 2 hours 15 minutes. The shortest flight path between them is 838 miles (1,349 km); winds and air traffic control usually add a few percent.
What does the New Orleans to Chicago flight path pass over?
The route crosses the Mississippi River valley near the Arkansas-Tennessee border, passing close to Memphis, then continues over flat farmland in the Missouri Bootheel and southern Illinois before approaching Chicago.