Southwest® flights from San Francisco to Chicago (O'Hare) from $83
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Low fares from San Francisco to Chicago (O'Hare)
$
San Francisco (SFO)to
Chicago (Midway) (MDW)
Depart: 02/03/2026
One-way
Basic
From
$72
Seen: 1 hour ago
San Francisco (SFO)to
Chicago (Midway) (MDW)
Depart: 02/04/2026
One-way
Basic
From
$72
Seen: 1 hour ago
San Francisco (SFO)to
Chicago (Midway) (MDW)
Depart: 02/26/2026
One-way
Basic
From
$81
Seen: 4 hrs ago
San Francisco (SFO)to
Chicago (Midway) (MDW)
Depart: 02/28/2026
One-way
Basic
From
$81
Seen: 3 hrs ago
San Francisco (SFO)to
Chicago (Midway) (MDW)
Depart: 01/31/2026
One-way
Basic
From
$81
Seen: 1 hour ago
San Francisco (SFO)to
Chicago (Midway) (MDW)
Depart: 01/20/2026
One-way
Basic
From
$83
Seen: 4 hrs ago
Explore flights from San Francisco to Chicago (O'Hare)
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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:
San Francisco International Airport
Arriving at:
O'Hare International Airport
Distance:
1846 miles
Route Information
84† Weekly flights
† 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 Chicago (O'Hare)
Towering over Lake Michigan, Chicago combines big-city energy with Midwestern hospitality. A day there really is whatever you choose to make of it. Millennium Park has plenty of attractions to explore. Take in a symphony at the unique Jay Pritzker Pavilion bandshell. Grab a selfie at Crown Fountain, a video sculpture and interactive piece of art. While your camera is out, be sure to head over to the Cloud Gate. Affectionally called “The Bean” due to its shape, this sculpture's shiny surface reflects and alters the view of the surrounding skyline. And you can walk under its 12-foot-high arch. If you have a hankering for ballet, modern dance, or opera, head to the Harris Theater for Music and Dance, which is also located on the grounds of this stunning downtown park.
Chicago is home to some of the most beautiful architecture in the country. A good example is the historic Water Tower, located along a stretch of Michigan Avenue aptly known as the Magnificent Mile. A former water pump building that withstood the Great Chicago Fire, it’s now home to the City Gallery, which features the works of local filmmakers, artists, and photographers. As you stroll down Michigan Avenue, famous for its shopping and busy sidewalks, you also take in other Chicago landmarks and architectural marvels like the Tribune Tower, Michigan Avenue Bridge and Esplanade, and the John Hancock Center.
Questions we hear the most
There are 84 weekly flights from San Francisco to Chicago (O'Hare) on Southwest Airlines.
To find the lowest fares by day and time to fly San Francisco to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
You can rent a car at O'Hare International Airport book yours with your flight.
Yes! Flights from San Francisco to Chicago (O'Hare)—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 San Francisco
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.