Cheap Flights from San Antonio (SAT) to Chicago (ORD) start at $61 for one-way and $115 for round trip. Earn your airline miles on top of our rewards!

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

Cheap Flights from Chicago (ORD) to San Antonio (SAT) start at $55 for one-way and $110 for round trip. Earn your airline miles on top of our rewards!

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Find the best deals on flights from San Antonio International (SAT) to Chicago O'Hare International (ORD). Compare prices from hundreds of major travel agents and airlines, all in one search.

Cheap Flights from San Antonio (SAT) to Chicago (MDW) start at $55 for one-way and $110 for round trip. Earn your airline miles on top of our rewards!