Southwest® flights from Chicago (Midway) to San Francisco from $72
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today
Low fares from Chicago (Midway) to San Francisco
$
Chicago (Midway) (MDW)to
San Francisco (SFO)
Depart: 02/18/2026
One-way
Basic
From
$72
Seen: 1 hour ago
Chicago (Midway) (MDW)to
San Francisco (SFO)
Depart: 01/10/2026
One-way
Basic
From
$81
Seen: 2 hrs ago
Chicago (Midway) (MDW)to
San Francisco (SFO)
Depart: 01/15/2026
One-way
Basic
From
$81
Seen: 1 hour ago
Chicago (Midway) (MDW)to
San Francisco (SFO)
Depart: 01/13/2026
One-way
Basic
From
$83
Seen: 1 hour ago
Chicago (Midway) (MDW)to
San Francisco (SFO)
Depart: 01/14/2026
One-way
Basic
From
$83
Seen: 1 hour ago
Chicago (Midway) (MDW)to
San Francisco (SFO)
Depart: 01/20/2026
One-way
Basic
From
$83
Seen: 8 minutes ago
Explore flights from Chicago (Midway) to San Francisco
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Travel tips for your next Southwest flight
How to board the plane earlier on open seating flights departing on or before January 26, 2026:
Southwest seats are first come, first served based on check-in order. But there are ways to board the plane earlier!
- Purchase EarlyBird Check-In®1 for automatic check-in and a better boarding position.
- Purchase Upgraded Boarding2 to get an A1-A15 boarding position (depending on availability).
- Purchase a Business Select® fare or upgrade to Business Select to get a guaranteed A1-A15 boarding position.
Enjoy movies, sips, and snacks during your flight.
Take advantage of inflight entertainment with free movies4, free live TV5, free texting6, and $8 inflight Internet7.
We also offer free sodas, coffee, and snacks8—learn more about the inflight food and beverage experience.
Make the most of our Rapid Rewards® Program.
Rapid Rewards Members can redeem their points for flights, hotel stays, rental cars, gift cards, and more. And your points never expire!
Flight Details
Departing from:
Chicago Midway International Airport
Arriving at:
San Francisco International Airport
Average flight time:
4 hours 31 minutes
Distance:
1855 miles
Route Information
158† Weekly flights
- 1‡ Nonstop flight per day Monday through Friday
- 1‡ Nonstop flight on Saturday
- 1‡ Nonstop flight on Sunday
† Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.
‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.
Explore San Francisco
Explore one of the United States' most beautiful cities—San Francisco! From the San Francisco Bay Area's beautiful wine country to its sandy beaches, there is plenty to do on foot and in the water to make your trip one to remember. For fun outdoor activities to enjoy with your friends or the whole family, make sure to check out Fisherman's Wharf, the premiere San Francisco location for great seafood and beautiful views of the ocean. Go to the beach, have some delicious clam chowder, and shop some of San Francisco's best souvenir shops. You'll enjoy the great energy and the natural beauty of this bustling attraction.
If you enjoy learning about U.S. history, San Francisco is a perfect city for you to visit. Rich with historical sites like the infamous Alcatraz Island, you'll get to enjoy taking a ferry ride to one of the West Coast's first lighthouses and forts. Of course, you might be more familiar with Alcatraz for the famous criminals it housed, such as Al Capone. Learn about the federal penitentiary's history and explore the island's wildlife. There is plenty of lush greenery to observe both on and off the island when you visit.
Questions we hear the most
The average flight time from Chicago (Midway) to San Francisco is 4 hours 31 minutes.
There are 158 weekly flights from Chicago (Midway) to San Francisco on Southwest Airlines.
Yes, Southwest flies nonstop from Chicago (Midway) to San Francisco once per day from Monday through Friday.
Yes, Southwest flies nonstop from Chicago (Midway) to San Francisco once per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Chicago (Midway) to San Francisco with Southwest, check out our Low Fare Calendar.
You can rent a car at San Francisco International Airport book yours with your flight.
Yes! Flights from Chicago (Midway) to San Francisco—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight.
Check out the Southwest Airlines® Help Center for answers about everything Southwest.
Explore Flights from Other Popular Origins
Popular Flights from Chicago (Midway)
1EarlyBird Check-In® pricing starts at $15 one-way, and is subject to availability. Pricing may vary based on the popularity and length of each (one-way) flight. Please see optional travel charges for more details.
2Upgraded boarding prices and benefits are per eligible segment. Flights must be within 24 hours of departure to be eligible for upgraded boarding.
3Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
4Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
5Texting only allows access to iMessage and WhatsApp (which must be downloaded and activated before connecting to SouthwestWiFi).
6Internet access for $8 per device from takeoff to landing. Price is subject to change. May not be available for the full duration of flight. In order to provide a top-notch Internet experience, we prohibit access to certain high-bandwidth applications and websites. We also prohibit access to certain obscene or offensive content.
7Flights traveling 175 miles or less will have only water available. Complimentary snacks are served on flights over 175 miles. If you’re flying between Hawaii and the continental U.S., you’ll have even more snacks to choose from.