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 23rd, 2026

7 round-trip options

Returning
Mon, Dec 28, 2026•5 Day Trip
$649 USD
Google Flights
Returning
Tue, Dec 29, 2026•6 Day Trip
$529 USD
Google Flights
Returning
Wed, Dec 30, 2026•7 Day Trip
$609 USD
Google Flights
Returning
Fri, Jan 1, 2027•9 Day Trip
$609 USD
Google Flights
Returning
Sun, Jan 3, 2027•11 Day Trip
$679 USD
Google Flights
Returning
Mon, Jan 4, 2027•12 Day Trip
$387 USD
Google Flights
Returning
Wed, Jan 6, 2027•14 Day Trip
$387 USD
Google Flights