The right side wins across all three phases: Chicago's skyline and Lake Michigan at takeoff, the Wyoming Rockies, Great Salt Lake, and Sierra Nevada peaks near Donner Pass during cruise, and San Francisco Bay's bridges and skyline on the descent into SFO. The left side sees mostly flat plains and desert basin with fewer distinct landmarks.
Flown MDW to SFO? Did we get it right?
Flight Path
Chicago to San Francisco is 1,850 miles (2,977 km), a flight of about 4 hours 25 minutes.
The route roughly follows the I-80 corridor, crossing the Rocky Mountains' front range near Laramie, Wyoming, passing close to the Great Salt Lake in Utah, traversing the Great Basin desert of Nevada, and crossing the Sierra Nevada near Donner Pass before descending into the San Francisco Bay Area.
Great circle distance and headings ›Phase by phase

Takeoff from MDW
RIGHTMidway departures typically head southeast or southwest before turning onto a westerly course, which swings the downtown Chicago skyline and Lake Michigan's shoreline into view on the north (right) side during the initial climb. The left side mostly shows Chicago's flat southern suburbs.

Landing at SFO
RIGHTOn the descent into SFO from the east, the approach path crosses the East Bay hills and San Francisco Bay, putting the San Francisco skyline, the Bay Bridge, and Golden Gate Bridge on the north (right) side of the aircraft. The left side instead overlooks the flatter Peninsula and South Bay salt flats.
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About This Route
Which side of the plane should I sit on flying from Chicago Midway International (MDW) to San Francisco International (SFO)?
Sit on the Right side of the plane for the best views on flights from Chicago to San Francisco. The right side wins across all three phases: Chicago's skyline and Lake Michigan at takeoff, the Wyoming Rockies, Great Salt Lake, and Sierra Nevada peaks near Donner Pass during cruise, and San Francisco Bay's bridges and skyline on the descent into SFO. The left side sees mostly flat plains and desert basin with fewer distinct landmarks.
What can I see during takeoff from Chicago Midway International in Chicago?
During takeoff from Chicago Midway International (MDW), sit on the Right side for the best views. Midway departures typically head southeast or southwest before turning onto a westerly course, which swings the downtown Chicago skyline and Lake Michigan's shoreline into view on the north (right) side during the initial climb. The left side mostly shows Chicago's flat southern suburbs. Notable sights include: Downtown Chicago skyline, Lake Michigan shoreline, Chicago's south side street grid.
What can I see when landing at San Francisco International in San Francisco?
When landing at San Francisco International (SFO), sit on the Right side for the best views. On the descent into SFO from the east, the approach path crosses the East Bay hills and San Francisco Bay, putting the San Francisco skyline, the Bay Bridge, and Golden Gate Bridge on the north (right) side of the aircraft. The left side instead overlooks the flatter Peninsula and South Bay salt flats. Notable sights include: San Francisco Bay, Golden Gate Bridge, downtown San Francisco skyline, Bay Bridge.
How long is the flight from Chicago to San Francisco?
The flight from Chicago Midway International (MDW) to San Francisco International (SFO) takes about 4 hours 25 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 Chicago to San Francisco flight path pass over?
The route roughly follows the I-80 corridor, crossing the Rocky Mountains' front range near Laramie, Wyoming, passing close to the Great Salt Lake in Utah, traversing the Great Basin desert of Nevada, and crossing the Sierra Nevada near Donner Pass before descending into the San Francisco Bay Area.