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
$450 USD
-43%$257 USD
Verified about 4 hours ago
Limited Availability
14% of dates checked are available within 10% of the lowest price

Friday, October 2nd, 2026

8 round-trip options

Returning
Wed, Oct 7, 2026•5 Day Trip
$338 USD
Google Flights
Returning
Thu, Oct 8, 2026•6 Day Trip
$459 USD
Google Flights
Returning
Fri, Oct 9, 2026•7 Day Trip
$419 USD
Google Flights
Returning
Sat, Oct 10, 2026•8 Day Trip
$338 USD
Google Flights
Returning
Sun, Oct 11, 2026•9 Day Trip
$529 USD
Google Flights
Returning
Tue, Oct 13, 2026•11 Day Trip
$338 USD
Google Flights
Returning
Wed, Oct 14, 2026•12 Day Trip
$338 USD
Google Flights
Returning
Thu, Oct 15, 2026•13 Day Trip
$354 USD
Google Flights