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 5 hours ago
Limited Availability
14% of dates checked are available within 10% of the lowest price

Wednesday, October 21st, 2026

8 round-trip options

Returning
Mon, Oct 26, 2026•5 Day Trip
$273 USD
Google Flights
Returning
Tue, Oct 27, 2026•6 Day Trip
$257 USD
Google Flights
Returning
Wed, Oct 28, 2026•7 Day Trip
$257 USD
Google Flights
Returning
Thu, Oct 29, 2026•8 Day Trip
$273 USD
Google Flights
Returning
Fri, Oct 30, 2026•9 Day Trip
$315 USD
Google Flights
Returning
Sun, Nov 1, 2026•11 Day Trip
$342 USD
Google Flights
Returning
Mon, Nov 2, 2026•12 Day Trip
$273 USD
Google Flights
Returning
Tue, Nov 3, 2026•13 Day Trip
$257 USD
Google Flights