San Francisco (SFO) to Chicago (MDW) flight deal in economy from $257
SFOSan Francisco International Airport
San Francisco, United States
MDWMidway International Airport
Chicago, United States
$450 USD
-43%$257 USD
Verified about 4 hours agoOctober 2026
Mon
Tue
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Limited Availability
14% of dates checked are available within 10% of the lowest price
Sunday, October 4th, 2026
8 round-trip options
Returning
Fri, Oct 9, 2026•5 Day Trip
$459 USD
Returning
Sat, Oct 10, 2026•6 Day Trip
$378 USD
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Sun, Oct 11, 2026•7 Day Trip
$569 USD
Returning
Mon, Oct 12, 2026•8 Day Trip
$703 USD
Returning
Tue, Oct 13, 2026•9 Day Trip
$378 USD
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Thu, Oct 15, 2026•11 Day Trip
$494 USD
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Fri, Oct 16, 2026•12 Day Trip
$536 USD
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Sat, Oct 17, 2026•13 Day Trip
$478 USD