San Francisco (SFO) to Chicago (MDW) flight deal in economy from $257

Delta Air LinesDLDelta Air Lines
Round Trip•Economy
United StatesSFO

San Francisco International Airport

San Francisco, United States
United StatesMDW

Midway International Airport

Chicago, United States
$450 USD
-43%$257 USD
Verified about 8 hours ago
Limited Availability
14% of dates checked are available within 10% of the lowest price

Wednesday, December 9th, 2026

7 round-trip options

Returning
Mon, Dec 14, 2026•5 Day Trip
$273 USD
Google Flights
Returning
Tue, Dec 15, 2026•6 Day Trip
$257 USD
Google Flights
Returning
Wed, Dec 16, 2026•7 Day Trip
$257 USD
Google Flights
Returning
Fri, Dec 18, 2026•9 Day Trip
$338 USD
Google Flights
Returning
Sun, Dec 20, 2026•11 Day Trip
$478 USD
Google Flights
Returning
Mon, Dec 21, 2026•12 Day Trip
$468 USD
Google Flights
Returning
Wed, Dec 23, 2026•14 Day Trip
$488 USD
Google Flights