Cheap Flights from Chicago (ORD) to San Antonio (SAT) start at $55 for one-way and $119 for round trip. Earn your airline miles on top of our rewards!

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Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to San Antonio. Discover the best prices and deals for you by selecting …

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Fly one-way from Chicago (Midway) to San Antonio starting at $174. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

Compare Chicago O'Hare International to San Antonio International flight deals. Find the cheapest month or even day of the year to fly to San Antonio International. Book the best San …

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Cheap Flights from Chicago (CHI) to San Antonio (SAT) start at $60 for one-way and $120 for round trip. Earn your airline miles on top of our rewards!

Fly one-way from Chicago (O'Hare) to San Antonio starting at $184. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.