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, August 29th, 2026

6 round-trip options

Returning
Thu, Sep 3, 2026•5 Day Trip
$378 USD
Google Flights
Returning
Sat, Sep 5, 2026•7 Day Trip
$267 USD
Google Flights
Returning
Sun, Sep 6, 2026•8 Day Trip
$728 USD
Google Flights
Returning
Tue, Sep 8, 2026•10 Day Trip
$728 USD
Google Flights
Returning
Thu, Sep 10, 2026•12 Day Trip
$321 USD
Google Flights
Returning
Sat, Sep 12, 2026•14 Day Trip
$277 USD
Google Flights