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

Friday, October 16th, 2026

6 round-trip options

Returning
Wed, Oct 21, 2026•5 Day Trip
$418 USD
Google Flights
Returning
Thu, Oct 22, 2026•6 Day Trip
$317 USD
Google Flights
Returning
Fri, Oct 23, 2026•7 Day Trip
$357 USD
Google Flights
Returning
Mon, Oct 26, 2026•10 Day Trip
$361 USD
Google Flights
Returning
Wed, Oct 28, 2026•12 Day Trip
$317 USD
Google Flights
Returning
Fri, Oct 30, 2026•14 Day Trip
$307 USD
Google Flights