Cheap flights from San Antonio to Chicago from $53
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Antonio to Chicago departing on 8/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Frontier flights from San Antonio to Chicago Midway Airport
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Southwest flights from San Antonio to Chicago Midway Airport
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How to get the cheapest flight ticket from San Antonio to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago Midway Airport?
The month of October is, on average, the cheapest month to fly to Chicago Midway Airport from San Antonio, with most prices found around $347. If you are unable to visit Chicago Midway Airport during the month of October, then departing from San Antonio during the month May is also very affordable. Most momondo users find prices during this month for around $367.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from San Antonio. The lowest ticket price found for a Wednesday departure recently was $406. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from San Antonio because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $436.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from San Antonio in the evening is the least expensive time of day to depart. momondo users have found prices as low as $237 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $434. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest San Antonio to Chicago Midway flight route?
Fly from San Antonio to Chicago Midway for the best San Antonio - Chicago Midway flight prices
What cabin class options are available on San Antonio to Chicago Midway flights?
There are 1 cabin classes available to choose from on San Antonio to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on San Antonio to Chicago Midway Airport flights?
You could potentially save up to 24% on your flight if you consider stops on a San Antonio to Chicago Midway Airport flight.
What is the cheapest airline that flies from San Antonio to Chicago Midway?
Frontier, Southwest, and Delta are the most popular carriers operating from San Antonio to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from San Antonio according to our data. Southwest is the first choice among our users, with 83% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from San Antonio to Chicago Midway Airport on average per day?
As of June 2025, there are 2 flights per day flying from San Antonio to Chicago Midway Airport. The most common time of day flights depart is 5:00AM, with 36% of flights taking off in the morning.
How many flights depart from San Antonio to Chicago Midway Airport on average per week?
14 flights are operational weekly from San Antonio to Chicago Midway Airport as of June 2025. The most popular departure day for this route is Mon, with 21% of flights per week taking off on this day.
When to book flights from San Antonio to Chicago Midway Airport
Cheap San Antonio to Chicago Midway Airport (SAT to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from San Antonio to Chicago Midway Airport
How far is San Antonio to Chicago Midway by plane?
The straight-line distance from San Antonio to Chicago Midway is 1043.4 mi. By plane, this route typically takes 2h 35m.
When did momondo last update prices for flights from San Antonio Airport to Chicago Midway Airport?
Prices for flights from San Antonio Airport to Chicago Midway Airport refresh daily.
How many operators does momondo search for flights from San Antonio Airport to Chicago Midway Airport?
As of June 2025, there are 3 operators available to choose from for flights from San Antonio Airport to Chicago Midway Airport.
How old do you have to be to fly from San Antonio Airport to Chicago Midway Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Antonio Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from San Antonio to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from San Antonio to Chicago Midway Airport is Boeing 737-800, representing 16.23% of all bookings. The subsequent popular models are Airbus A319 at 13.25%, Boeing 737-700 Passenger/BBJ1 (winglets) at 12.87%, and Boeing 737 MAX 8 at 11.19%.
What is the most popular airline from San Antonio to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from San Antonio to Chicago Midway Airport is Southwest (82% of total bookings). The next most popular airlines are Delta (9%) and Frontier (9%).
Best airlines flying from San Antonio to Chicago Midway Airport
Compare and see reviews for airlines that fly from San Antonio to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $147 | Free Cancellation | Rating 5.9 3,290 reviews | |||
| PriceFrom $235 | Free Cancellation | Rating 8.0 4,278 reviews | |||
| PriceFrom $241 | Free Cancellation | Rating 8.0 7,973 reviews |
Southwest Flights From San Antonio to Chicago Midway Airport
Southwest flies from San Antonio to Chicago Midway Airport around 14 times per week, with 4,278 momondo users rating the airline 8.0/10. The cheapest Southwest deal from San Antonio to Chicago Midway Airport in the last 72 hours was $235 (round-trip), much lower than the average airfare cost of $427 for Southwest flights on this route.
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Why should I use momondo to find a flight deal from San Antonio to Chicago?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from San Antonio to Chicago. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from San Antonio to Chicago with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for San Antonio to Chicago flights to just show those with flexible booking policies.
How can momondo help me find flights from San Antonio to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from San Antonio.
I’m not ready to book a flight from San Antonio to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for San Antonio to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.