Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 321,000 hotels worldwide and 400 airlines worldwide.

Secure incredible value with Expedia's Price Guarantee.

No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheap SAT to MDW Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Chicago

$223.00

Cheap SAT to MDW Flights

Question : What day has the most flight time options?
Answer : Saturday has the greatest variety of flight times for San Antonio to Chicago with seven. Thursday currently offers the fewest number of flight times with only four options.

Question : How often is the San Antonio International Airport (SAT) to Chicago Midway International Airport (MDW) route delayed?
Answer : This particular route gets passengers to Chicago Midway International Airport on time 80% of the time, which puts it in the top 50% of the world. If a flight is late, though, expect an average of less than half an hour added to your flight time.

Question : What day in the next four weeks has the best fares?
Answer : As of Jan 15th, the best day for deals to Chicago (MDW) is Feb 6th. It costs $210, which is 62% below the average price to book the same route.

Question : What's the likelihood of you being delayed on this route?
Answer : SAT to MDW currently scores 3 out of a possible 5 stars in promptness. This score combines both the number of delayed flights and total delay minutes. With 3 stars, you should feel slightly worried about getting to Chicago on time.

Question : Which airline is struggling to get to Chicago on time?
Answer : If you decide to book your flight with Delta Air Lines, keep an eye on your departure time. 67% of flights from San Antonio International Airport (SAT) to Chicago Midway International Airport (MDW) are late.

Question : Have you considered flying into O'Hare International Airport instead of Chicago Midway International Airport?
Answer : Luckily for you, there is another airport near Chicago. O'Hare International Airport (ORD) is 16 miles away, and over the next two months flights are being booked 34% cheaper than flights to Chicago Midway International Airport.

Question : Do travelers from San Antonio typically stay in Chicago for very long?
Answer : Over the next two months, passengers from SAT to MDW are planning on staying for four days on average.

San Antonio to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from San Antonio to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with SAT to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind San Antonio for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MDW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.