The left side wins on both ends of the flight: San Diego's bay-and-skyline departure and Chicago's skyline-and-lake arrival both favor that side, while the right side mostly faces open ocean at takeoff and flat suburban sprawl at landing, with the featureless plains in between offering no advantage to either side.
Flown SAN to MDW? Did we get it right?
Flight Path
San Diego to Chicago is 1,725 miles (2,776 km), a flight of about 3 hours 55 minutes.
Sonoran Desert and mountain ranges of southern Arizona, the Rio Grande valley near Albuquerque, the high plains of the Texas and Oklahoma panhandles, and the flat farmland of Kansas, Missouri, and Illinois as the route flattens out toward Chicago
Great circle distance and headings ›
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Phase by phase
Takeoff from SAN
LEFTSAN's Runway 27 departure sends the aircraft west over San Diego Bay before it banks to head east toward Chicago, and that turn puts downtown San Diego, the bay, and Coronado on the left side of the cabin. It's one of the most scenic standard departures in the US before the route settles into desert and plains.
Landing at MDW
LEFTOn the common northwest approach to Runway 13C, the flight path curls over Chicago's south side before final descent, giving left-side passengers a clear look at the Loop skyline and a sliver of Lake Michigan just before landing at Midway's compact, urban airfield.
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About This Route
Which side of the plane should I sit on flying from San Diego International Lindbergh Fld (SAN) to Chicago Midway International (MDW)?
Sit on the Left side of the plane for the best views on flights from San Diego to Chicago. The left side wins on both ends of the flight: San Diego's bay-and-skyline departure and Chicago's skyline-and-lake arrival both favor that side, while the right side mostly faces open ocean at takeoff and flat suburban sprawl at landing, with the featureless plains in between offering no advantage to either side.
What can I see during takeoff from San Diego International Lindbergh Fld in San Diego?
During takeoff from San Diego International Lindbergh Fld (SAN), sit on the Left side for the best views. SAN's Runway 27 departure sends the aircraft west over San Diego Bay before it banks to head east toward Chicago, and that turn puts downtown San Diego, the bay, and Coronado on the left side of the cabin. It's one of the most scenic standard departures in the US before the route settles into desert and plains. Notable sights include: San Diego Bay, Coronado Bridge, Downtown San Diego skyline, Point Loma peninsula.
What can I see when landing at Chicago Midway International in Chicago?
When landing at Chicago Midway International (MDW), sit on the Left side for the best views. On the common northwest approach to Runway 13C, the flight path curls over Chicago's south side before final descent, giving left-side passengers a clear look at the Loop skyline and a sliver of Lake Michigan just before landing at Midway's compact, urban airfield. Notable sights include: Chicago Loop skyline, Willis Tower, Lake Michigan shoreline, south side Chicago neighborhoods.
How long is the flight from San Diego to Chicago?
The flight from San Diego International Lindbergh Fld (SAN) to Chicago Midway International (MDW) takes about 3 hours 55 minutes. The shortest flight path between them is 1,725 miles (2,776 km); winds and air traffic control usually add a few percent.
What does the San Diego to Chicago flight path pass over?
Sonoran Desert and mountain ranges of southern Arizona, the Rio Grande valley near Albuquerque, the high plains of the Texas and Oklahoma panhandles, and the flat farmland of Kansas, Missouri, and Illinois as the route flattens out toward Chicago