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
$456 USD
-44%$257 USD
Verified 13 days ago
Limited Availability
17% of dates checked are available within 10% of the lowest price

Saturday, November 21st, 2026

6 round-trip options

Returning
Thu, Nov 26, 2026•5 Day Trip
$311 USD
Google Flights
Returning
Fri, Nov 27, 2026•6 Day Trip
$682 USD
Google Flights
Returning
Sat, Nov 28, 2026•7 Day Trip
$752 USD
Google Flights
Returning
Tue, Dec 1, 2026•10 Day Trip
$472 USD
Google Flights
Returning
Thu, Dec 3, 2026•12 Day Trip
$321 USD
Google Flights
Returning
Sat, Dec 5, 2026•14 Day Trip
$321 USD
Google Flights