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, August 14th, 2026

6 round-trip options

Returning
Wed, Aug 19, 2026•5 Day Trip
$556 USD
Google Flights
Returning
Fri, Aug 21, 2026•7 Day Trip
$590 USD
Google Flights
Returning
Sat, Aug 22, 2026•8 Day Trip
$448 USD
Google Flights
Returning
Mon, Aug 24, 2026•10 Day Trip
$448 USD
Google Flights
Returning
Wed, Aug 26, 2026•12 Day Trip
$448 USD
Google Flights
Returning
Fri, Aug 28, 2026•14 Day Trip
$488 USD
Google Flights