Both sides score equally at 2.0 due to the short flight duration (approximately 1 hour) over flat Midwestern terrain with minimal dramatic geography. However, left side edges ahead for the landing sequence, which provides views of Chicago's urban sprawl and Lake Michigan shoreline—the only visually distinctive features on this route. The takeoff from Evansville is marginally better on the right, but the landing advantage on the left makes it the overall recommendation.
Flown EVV to ORD? Did we get it right?
Flight Path
Evansville to Chicago is 273 miles (439 km), a flight of about 1 hour 5 minutes.
Flat agricultural plains of southern Illinois, scattered small towns and county roads, minimal elevation change throughout the route. No mountains, significant water bodies, or dramatic terrain features visible from cruise altitude.
Great circle distance and headings ›Phase by phase
Takeoff from EVV
RIGHTRight side offers a brief view of the Ohio River valley and Evansville's urban area during initial climb before the aircraft turns northward. Left side faces open farmland with minimal visual interest during departure.

Landing at ORD
LEFTLeft side provides views of the Chicago metropolitan area, Lake Michigan shoreline, and the approach corridor over the city's western suburbs during descent into ORD. Right side faces open water and lacks urban visual interest during final approach.
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 Evansville Regional Airport (EVV) to Chicago Ohare International (ORD)?
Sit on the Left side of the plane for the best views on flights from Evansville to Chicago. Both sides score equally at 2.0 due to the short flight duration (approximately 1 hour) over flat Midwestern terrain with minimal dramatic geography. However, left side edges ahead for the landing sequence, which provides views of Chicago's urban sprawl and Lake Michigan shoreline—the only visually distinctive features on this route. The takeoff from Evansville is marginally better on the right, but the landing advantage on the left makes it the overall recommendation.
What can I see during takeoff from Evansville Regional Airport in Evansville?
During takeoff from Evansville Regional Airport (EVV), sit on the Right side for the best views. Right side offers a brief view of the Ohio River valley and Evansville's urban area during initial climb before the aircraft turns northward. Left side faces open farmland with minimal visual interest during departure. Notable sights include: Ohio River (south of EVV), Evansville downtown grid, agricultural plains extending north.
What can I see when landing at Chicago Ohare International in Chicago?
When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. Left side provides views of the Chicago metropolitan area, Lake Michigan shoreline, and the approach corridor over the city's western suburbs during descent into ORD. Right side faces open water and lacks urban visual interest during final approach. Notable sights include: Lake Michigan (eastern edge of approach), Chicago skyline (downtown Loop visible from distance), suburban sprawl of western Chicago, Des Plaines River valley.
How long is the flight from Evansville to Chicago?
The flight from Evansville Regional Airport (EVV) to Chicago Ohare International (ORD) takes about 1 hour 5 minutes. The shortest flight path between them is 273 miles (439 km); winds and air traffic control usually add a few percent.
What does the Evansville to Chicago flight path pass over?
Flat agricultural plains of southern Illinois, scattered small towns and county roads, minimal elevation change throughout the route. No mountains, significant water bodies, or dramatic terrain features visible from cruise altitude.