$140+ Cheap flights from Midway (MDW) to San Antonio (SAT)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAT
Oct 6 — Oct 131
Round-trip
1 adult, Economy
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Find cheap flights from Midway to San Antonio with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to San Antonio
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Best
Last-minute
One-way
Cheapest flights from Midway to San AntonioExplore the most affordable flight options available from Midway to San Antonio. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 6, 2026.
Explore the most affordable flight options available from Midway to San Antonio. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 6, 2026.
This CheapOair deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:42 pm -
1 stop14h 29m
Fri 11/2712:06 pm -
1 stop7h 41m
Deal found 9/4![Frontier logo]()
$359
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:20 pm -
Nonstop2h 50m
Mon 10/192:35 pm -
Nonstop2h 40m
Deal found 9/3![Southwest logo]()
$365
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/301:55 pm -
1 stop4h 00m
Wed 10/78:55 am -
Nonstop2h 40m
Deal found 9/2![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1011:35 am -
Nonstop2h 45m
Sat 10/2410:05 am -
2 stops5h 10m
Deal found 9/1![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:30 am -
2 stops6h 40m
Wed 11/49:50 am -
Nonstop2h 30m
Deal found 9/2![Southwest logo]()
$380
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:30 pm -
Nonstop2h 55m
Tue 12/19:50 am -
Nonstop2h 30m
Deal found 9/3![Southwest logo]()
$381
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:35 pm -
Nonstop2h 45m
Mon 9/283:30 pm -
1 stop3h 50m
Deal found 9/3![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/242:20 pm -
2 stops6h 20m
Mon 10/2612:20 pm -
1 stop5h 15m
Deal found 9/2![Southwest logo]()
$390
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:10 am -
2 stops5h 40m
Tue 10/1312:55 pm -
2 stops6h 30m
Deal found 9/2![Southwest logo]()
$395
Best flights from Midway to San AntonioDiscover carefully curated flight deals from Midway to San Antonio that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 6, 2026.
Discover carefully curated flight deals from Midway to San Antonio that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 6, 2026.
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 pm -
1 stop5h 40m
Mon 10/2612:20 pm -
1 stop5h 15m
Deal found 9/2![Southwest logo]()
$385
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:29 am -
1 stop6h 24m
Mon 10/54:21 pm -
1 stop6h 23m
Deal found 9/1![Delta logo]()
$400
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:30 pm -
Nonstop2h 55m
Tue 12/13:30 pm -
1 stop7h 10m
Deal found 9/5![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:30 am -
1 stop5h 30m
Tue 10/138:55 am -
Nonstop2h 40m
Deal found 9/5![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:20 pm -
Nonstop2h 50m
Tue 10/2711:25 am -
2 stops5h 45m
Deal found 9/4![Southwest logo]()
$412
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:30 pm -
Nonstop2h 55m
Fri 11/279:15 am -
Nonstop2h 40m
Deal found 9/4![Southwest logo]()
$415
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/119:25 pm -
Nonstop2h 50m
Wed 10/142:25 pm -
Nonstop2h 40m
Deal found 9/2![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:20 pm -
Nonstop2h 50m
Mon 10/2611:40 am -
1 stop3h 50m
Deal found 9/4![Southwest logo]()
$425
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:20 am -
1 stop7h 00m
Sun 11/229:15 am -
Nonstop2h 40m
Deal found 9/3![Southwest logo]()
$429
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:45 am -
Nonstop2h 45m
Sun 10/49:20 am -
Nonstop2h 40m
Deal found 9/3![Southwest logo]()
$434
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:45 pm -
Nonstop2h 50m
Thu 10/152:35 pm -
Nonstop2h 40m
Deal found 9/3![Southwest logo]()
$445
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/191:50 pm -
Nonstop2h 45m
Sat 9/2612:20 pm -
1 stop7h 00m
Deal found 9/1![Southwest logo]()
$460
Last-minute flights from Midway to San AntonioDiscover last-minute flight deals from Midway to San Antonio. Data last updated September 6, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Antonio. Data last updated September 6, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:35 pm -
Nonstop2h 45m
Mon 9/283:30 pm -
1 stop3h 50m
Deal found 9/3![Southwest logo]()
$386
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:05 am -
1 stop6h 44m
Wed 9/305:30 am -
1 stop6h 24m
Deal found 9/2![Delta logo]()
$385
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/301:55 pm -
1 stop4h 00m
Wed 10/78:55 am -
Nonstop2h 40m
Deal found 9/2![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/89:20 pm -
Nonstop2h 50m
Mon 10/124:45 pm -
1 stop6h 30m
Deal found 9/2![Southwest logo]()
$375
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/134:30 pm -
1 stop6h 35m
Fri 10/163:20 pm -
1 stop6h 05m
Deal found 9/3![Southwest logo]()
$400
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:20 pm -
Nonstop2h 50m
Mon 10/192:35 pm -
Nonstop2h 40m
Deal found 9/3![Southwest logo]()
$365
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:20 pm -
Nonstop2h 50m
Sat 10/2410:05 am -
2 stops5h 10m
Deal found 9/2![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:20 pm -
Nonstop2h 50m
Tue 10/278:55 am -
Nonstop2h 40m
Deal found 9/6![Southwest logo]()
$397
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:55 am -
2 stops5h 20m
Tue 11/39:50 am -
Nonstop2h 30m
Deal found 9/1![Southwest logo]()
$395
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:30 am -
2 stops6h 40m
Wed 11/49:50 am -
Nonstop2h 30m
Deal found 9/2![Southwest logo]()
$380
One-way flights from Midway to San AntonioSearch for one-way flight options from Midway to San Antonio. Find affordable one-way fares based on user searches. Data last updated September 6, 2026.
Search for one-way flight options from Midway to San Antonio. Find affordable one-way fares based on user searches. Data last updated September 6, 2026.
This CheapOair deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:07 pm -
1 stop24h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$140
This CheapOair deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:42 pm -
1 stop14h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$160
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:20 pm -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Southwest logo]()
$183
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/301:55 pm -
1 stop4h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Southwest logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:25 am -
2 stops26h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Frontier logo]()
$189
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1312:05 pm -
1 stop6h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Southwest logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2812:54 pm -
2 stops30h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$197
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/48:50 pm -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Southwest logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:25 am -
2 stops26h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:21 am -
2 stops26h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Multiple Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:15 am -
1 stop4h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Southwest logo]()
$208
Find flight deals from Midway to San Antonio
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Antonio (SAT). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $359 (CheapOair) |
One-way from | $140 (CheapOair) |
Popular in | July |
Cheapest in | October |
Average price | $431 |
Good round-trip deal | $357 or less |
Good one-way deal | $148 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to San Antonio that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 6, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San Antonio that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Mon 11/23
9:30 pm-12:20 am
Nonstop2h 50m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$183
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Sat 10/24
6:20 pm-9:10 pm
Nonstop2h 50m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$183
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Wed 10/14
6:04 am-12:35 pm
1 stop6h 31m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$193
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Tue 10/13
5:40 am-10:45 am
1 stop5h 05m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$193
Quickest round-trip
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Fri 10/30
9:45 am-12:30 pm
Nonstop2h 45m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$198
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Fri 11/6
4:19 pm-11:26 pm
1 stop7h 07m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$208
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Fri 12/4
12:39 pm-5:48 pm
1 stop5h 09m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$208
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Thu 11/5
6:25 pm-11:25 pm
1 stop5h 00m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$209
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Thu 10/22
6:00 pm-11:40 pm
1 stop5h 40m
San Antonio
Mon 10/26
12:20 pm-5:35 pm
1 stop5h 15m
$385
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Fri 10/2
9:29 am-3:53 pm
1 stop6h 24m
San Antonio
Mon 10/5
4:21 pm-10:44 pm
1 stop6h 23m
$400
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from Midway to San Antonio
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to San Antonio in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-San Antonio flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-San Antonio flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San Antonio flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-San Antonio flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-San Antonio flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to San Antonio
Have a flexible travel schedule? Discover the best time to fly to San Antonio from Midway with our price prediction graph.
MDW-SAT
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to San Antonio
What is the cheapest month to book a flight from Chicago Midway Airport to San Antonio?
Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to San Antonio (average of $257). Flying from Chicago Midway Airport to San Antonio in July is currently the most expensive (average of $764). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to SAT?
Find hourly flight availability from Midway to San Antonio. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 6, 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 15% on flights from Chicago Midway Airport to San Antonio by exploring options for tickets in the evening.
The best insider tips for Chicago Midway Airport to San Antonio flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to San Antonio trip
Our travel experts
Reviews of airlines servicing San Antonio
Get insights into the airlines that provide service to San Antonio. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Antonio. Reviews last updated September 6, 2026.
Read reviews from past customers who have flown Southwest and Frontier from Chicago Midway Airport to San Antonio. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
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Top 2 airlines flying from Midway to San Antonio
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$200 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$297 | Average$443 | FlexibilityNo cancel fee | On-time63% |