The left side delivers a more complete scenic arc: San Francisco Bay and skyline at takeoff, glimpses of the Sierra Nevada near Lake Tahoe and the Great Salt Lake basin during cruise, and Chicago's skyline with Lake Michigan on arrival, while the right side offers mostly flat, featureless terrain throughout.
Flown SFO to MDW? Did we get it right?
Flight Path
San Francisco to Chicago is 1,850 miles (2,977 km), a flight of about 4 hours 15 minutes.
Sierra Nevada near Lake Tahoe, Great Salt Lake basin, Rocky Mountain foothills of southern Wyoming/northern Colorado, and the flat farmland of Nebraska and Iowa
Great circle distance and headings ›Phase by phase

Takeoff from SFO
LEFTDeparting SFO to the east-southeast, the aircraft climbs away from the peninsula with San Francisco's skyline, the Bay Bridge, and the Oakland/Berkeley hills receding on the left side. The right side mostly shows the flatter San Mateo/Silicon Valley corridor.

Landing at MDW
LEFTOn approach into Midway from the northwest, the descent path puts Lake Michigan and the downtown Chicago skyline on the left side of the aircraft, while the right side faces flat suburban terrain with little visual interest.
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About This Route
Which side of the plane should I sit on flying from San Francisco International (SFO) to Chicago Midway International (MDW)?
Sit on the Left side of the plane for the best views on flights from San Francisco to Chicago. The left side delivers a more complete scenic arc: San Francisco Bay and skyline at takeoff, glimpses of the Sierra Nevada near Lake Tahoe and the Great Salt Lake basin during cruise, and Chicago's skyline with Lake Michigan on arrival, while the right side offers mostly flat, featureless terrain throughout.
What can I see during takeoff from San Francisco International in San Francisco?
During takeoff from San Francisco International (SFO), sit on the Left side for the best views. Departing SFO to the east-southeast, the aircraft climbs away from the peninsula with San Francisco's skyline, the Bay Bridge, and the Oakland/Berkeley hills receding on the left side. The right side mostly shows the flatter San Mateo/Silicon Valley corridor. Notable sights include: San Francisco skyline, San Francisco Bay, Bay Bridge, Oakland-Berkeley hills.
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 approach into Midway from the northwest, the descent path puts Lake Michigan and the downtown Chicago skyline on the left side of the aircraft, while the right side faces flat suburban terrain with little visual interest. Notable sights include: Lake Michigan shoreline, Chicago downtown skyline, Willis Tower, Chicago suburbs grid.
How long is the flight from San Francisco to Chicago?
The flight from San Francisco International (SFO) to Chicago Midway International (MDW) takes about 4 hours 15 minutes. The shortest flight path between them is 1,850 miles (2,977 km); winds and air traffic control usually add a few percent.
What does the San Francisco to Chicago flight path pass over?
Sierra Nevada near Lake Tahoe, Great Salt Lake basin, Rocky Mountain foothills of southern Wyoming/northern Colorado, and the flat farmland of Nebraska and Iowa