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
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Limited Availability
14% of dates checked are available within 10% of the lowest price
Saturday, October 3rd, 2026
8 round-trip options
Returning
Thu, Oct 8, 2026•5 Day Trip
$378 USD
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Fri, Oct 9, 2026•6 Day Trip
$338 USD
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Sat, Oct 10, 2026•7 Day Trip
$257 USD
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Sun, Oct 11, 2026•8 Day Trip
$448 USD
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Mon, Oct 12, 2026•9 Day Trip
$618 USD
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Wed, Oct 14, 2026•11 Day Trip
$257 USD
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Thu, Oct 15, 2026•12 Day Trip
$273 USD
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Fri, Oct 16, 2026•13 Day Trip
$315 USD