Southwest® flights from San Antonio to Chicago (O'Hare) from $150
expand_more
1 Passenger
expand_morePromo Code
expand_moretoday
today
Low fares from San Antonio to Chicago (O'Hare)
$
San Antonio (SAT)to
Chicago (Midway) (MDW)
Depart: 01/14/2026
One-way
Basic
From
$73
Seen: 1 hour ago
San Antonio (SAT)to
Chicago (Midway) (MDW)
Depart: 03/03/2026
One-way
Basic
From
$73
Seen: 35 minutes ago
San Antonio (SAT)to
Chicago (Midway) (MDW)
Depart: 01/06/2026
One-way
Basic
From
$77
Seen: 1 hour ago
San Antonio (SAT)to
Chicago (Midway) (MDW)
Depart: 01/27/2026
One-way
Basic
From
$87
Seen: 18 minutes ago
San Antonio (SAT)to
Chicago (Midway) (MDW)
Depart: 01/08/2026
One-way
Basic
From
$91
Seen: 43 minutes ago
San Antonio (SAT)to
Chicago (Midway) (MDW)
Depart: 03/03/2026
One-way
Choice
From
$93
Seen: 35 minutes ago
Explore flights from San Antonio to Chicago (O'Hare)
location_on
location_on
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 Antonio International Airport
Arriving at:
O'Hare International Airport
Distance:
1041 miles
Route Information
140† 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)
No matter when you choose to visit Chicago, you’re in for weather quite unlike anything back home in Texas. Thanks to being on the shore of Lake Michigan, the Windy City has humid summers and snowy winters—sometimes exceptionally so. Don’t fret: Chicago has plenty of indoor activities if you need to get out of the elements, and the City in the Garden is full of parks that are picture perfect examples of municipal parkland all year long.
Whether you’re packing snow boots or swimsuits, plan to partake in at least one slice of Chicago-style pizza while you’re in town. And, no: Chicago-style pizza is not the deep dish tomato sauce-topped pie you’ve seen comedians poke fun at. Thin crust, tavern cut pizza is what locals will lead you to. Rather take down a couple of hotdogs? Try one Chicago-style: covered in mustard, relish, onion, tomato, celery salt, sport peppers, and a pickle spear. If “dragged through the garden” doesn’t sound good, just make sure not to garnish your dog with ketchup.
Questions we hear the most
There are 140 weekly flights from San Antonio to Chicago (O'Hare) on Southwest Airlines.
To find the lowest fares by day and time to fly San Antonio 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 Antonio 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 Antonio
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.