Wing your way to the Windy City with a flight on Southwest Airlines. Southwest flies from San Antonio International Airport to Chicago O’Hare International Airport with ticket prices that’ll make choosing to get away simple. If you have flexible travel dates, explore our Low Fare Calendar to find low fares within your travel window. Make the most of your reservation with package deals on flights, hotels, rental cars, and more from Southwest Vacations®.
Start marking off the days until you depart Countdown City with Southwest!
San Antonio, TX to Chicago (O'Hare), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 16 travel days available.
Departing from | San Antonio International Airport (SAT) |
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Arriving at | Chicago O'Hare International Airport (ORD) |
Distance | 1041 miles |
57† | Weekly flights |
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Other popular flights from San Antonio:
View our interactive map†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 4/1/2024 and 4/30/2024. Note: route may not operate every day of the week.
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.
While it may be hard to choose what to do during your visit, getting around is easy when you hop on the CTA. The buses and trains traverse the 77 neighborhoods that make up Chicago, inviting you to explore whatever you wish from Uptown to the Back of the Yards.
One child over 14 days and under two (2) years of age, not occupying a seat, may be carried free of charge when traveling with an adult (12 years of age or older). Learn more.
Customers flying with a pet are subject to a pet fare. To learn more about traveling with your furry friend, explore the Southwest® pet policy.
Minors under the age of 18 are not permitted to fly unaccompanied on international flights or any itinerary that includes an international flight. Learn more.
At Southwest, we know it takes more than great deals on Chicago (O'Hare) airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from San Antonio to Chicago (O'Hare) the best it can be. Learn more about the Southwest® travel experience before you book your flight from San Antonio International Airport to Chicago O'Hare International Airport.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to Chicago (O'Hare), know that you won’t be surprised at checkout. Low fares and no hidden fees. That's Transfarency®. And as always, two bags fly free®1. Want the latest news, information, and promotional offers from Southwest? Sign up to receive email from us. Book your flight today and know that you'll earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
3Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.
4Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.
5Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
6Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
7Internet 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.