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

Thursday, October 1st, 2026

6 round-trip options

Returning
Tue, Oct 6, 2026•5 Day Trip
$277 USD
Google Flights
Returning
Wed, Oct 7, 2026•6 Day Trip
$277 USD
Google Flights
Returning
Thu, Oct 8, 2026•7 Day Trip
$321 USD
Google Flights
Returning
Sun, Oct 11, 2026•10 Day Trip
$428 USD
Google Flights
Returning
Tue, Oct 13, 2026•12 Day Trip
$277 USD
Google Flights
Returning
Thu, Oct 15, 2026•14 Day Trip
$321 USD
Google Flights