Flights from San Francisco to Chicago Midway

Our cheapest offers for flights from San Francisco to Chicago Midway

Here you can compare cheap flights from San Francisco (SFO) to Chicago Midway (MDW) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Chicago Midway. Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Best option
San Francisco
Chicago Midway
Outbound
10/18/25
direct
WN0698
04h 05min
Return
10/22/25
direct
WN1193
04h 30min
Southwest Airlines ?
$244
San Francisco
Chicago Midway
Outbound
10/18/25
1 Stopover (ATL)
F91448, F92779
23h 02min
Return
10/22/25
2 Stopovers (ATL, DEN)
F92292, F91449, F91093
16h 22min
Frontier Airlines ?
$494
Prices based on recent searches, subject to last-minute changes
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Tips and tricks to help you find cheap flights from San Francisco to Chicago Midway

Favorite airline: Frontier Airlines
The favorite airline for flights from San Francisco to Chicago Midway is Frontier Airlines.
Frontier Airlines
91 %
Delta
8 %
Alaska Airlines
2 %
Direct flights are the cheapest connection
Direct flights on this route are $52.00 cheaper on average than flights with a stopover.
non stop flight
1 stop
2 stops
04h 13min
10h 49min
09h 58min
$112
$164
$861
The favorite connection is non-stop
Non-stop flights are especially popular on this route. 69 % of travelers will book a direct flight.
Route
bookings
Direct flights
04h 13min, from $112
69 %
1 stopover Las Vegas - McCarran International Airport, NV
10h 49min, from $164
15 %
1 stopover Hartsfield-Jackson Atlanta International Airport, GA
10h 56min, from $174
10 %

Important flight information

Flight information: San Francisco - Chicago Midway

Roundtrip from $243.20
Flight duration min. 04:00 / max. 07:10
Return flight duration min. 04:55/ max. 11:40
Distance 2981 km
Flights per week 17
Departure airport Airport San Francisco International Airport, CA (SFO)
Arrival airport Airport Chicago Midway International Airport, IL (MDW)
Destination country Flights to United States
Alternative routes to United States
Alternative flights to Chicago Midway
Flight destinations with a similar price