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!

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Flights from San Antonio to Chicago. Use Google Flights to plan your next trip and find cheap one way or round trip flights from San Antonio to Chicago.

Find United Airlines cheap flights from San Antonio to Chicago. Enjoy a San Antonio to Chicago modern flight experience in premium cabins with Wi-Fi.

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.

Find flights to Chicago from $49. Fly from San Antonio on Frontier, Spirit Airlines and more. Search for Chicago flights on KAYAK now to find the best deal.

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

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!

Find flights to Chicago Midway Airport from $50. Fly from San Antonio on Frontier, Southwest, Delta and more. Search for Chicago Midway Airport flights on KAYAK now to find the best deal.

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.