$149+ Cheap flights from Midway (MDW) to San Antonio (SAT)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAT
Aug 12 — Aug 191
Round-trip
1 adult, Economy
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Find cheap flights from Midway to San Antonio with Cheapflights
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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
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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 July 13, 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 July 13, 2026.
This Southwest deal was found by Cheapflights users on 7/10. 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 8/78:35 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Mon 8/103:30 pm
SAT
- MDW
1 stop3h 50m
Southwest
Deal found 7/10![Southwest logo]()
$271
This Southwest deal was found by Cheapflights users on 7/10. 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 9/121:50 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Sat 9/1911:10 am
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 7/10![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 7/10. 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 8/48:30 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Tue 8/111:30 pm
SAT
- MDW
1 stop7h 10m
Southwest
Deal found 7/10![Southwest logo]()
$274
This Southwest deal was found by Cheapflights users on 7/9. 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 10/99:20 pm
MDW
- SAT
Nonstop2h 45m
Southwest
Mon 10/124:45 pm
SAT
- MDW
1 stop6h 25m
Southwest
Deal found 7/9![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 7/8. 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
MDW
- SAT
Nonstop2h 40m
Southwest
Thu 10/15:00 pm
SAT
- MDW
1 stop6h 05m
Southwest
Deal found 7/8![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 7/8. 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 8/191:55 pm
MDW
- SAT
1 stop4h 00m
Southwest
Fri 8/213:30 pm
SAT
- MDW
1 stop3h 50m
Southwest
Deal found 7/8![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 7/8. 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 8/64:45 pm
MDW
- SAT
1 stop5h 40m
Southwest
Mon 8/103:30 pm
SAT
- MDW
1 stop3h 50m
Southwest
Deal found 7/8![Southwest logo]()
$281
This deal was found by Cheapflights users on 7/10. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/239:30 am
MDW
- SAT
1 stop5h 34m
Delta
Tue 12/16:30 am
SAT
- MDW
1 stop5h 21m
Delta
Deal found 7/10![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 7/9. 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 10/2310:58 am
MDW
- SAT
1 stop6h 17m
Delta
Sat 10/315:30 am
SAT
- MDW
1 stop5h 08m
Delta
Deal found 7/9![Delta logo]()
$285
This Southwest deal was found by Cheapflights users on 7/9. 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.
Mon 8/105:25 am
MDW
- SAT
1 stop5h 45m
Southwest
Fri 8/141:00 pm
SAT
- MDW
1 stop5h 15m
Southwest
Deal found 7/9![Southwest logo]()
$286
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 July 13, 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 July 13, 2026.
This Southwest deal was found by Cheapflights users on 7/12. 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 9/88:30 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Tue 9/159:25 am
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 7/12![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 7/12. 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 10/1011:35 am
MDW
- SAT
1 stop5h 40m
Delta
Thu 10/156:45 am
SAT
- MDW
1 stop5h 20m
Delta
Deal found 7/12![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 7/10. 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.
Mon 8/248:35 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Mon 8/315:00 am
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 7/10![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 7/9. 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 8/64:45 pm
MDW
- SAT
1 stop5h 40m
Southwest
Mon 8/1011:10 am
SAT
- MDW
2 stops5h 45m
Southwest
Deal found 7/9![Southwest logo]()
$324
This Delta deal was found by Cheapflights users on 7/8. 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.
Sun 9/139:59 am
MDW
- SAT
1 stop7h 11m
Delta
Wed 9/1610:59 am
SAT
- MDW
1 stop5h 17m
Delta
Deal found 7/8![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 7/10. 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 8/2710:10 am
MDW
- SAT
2 stops6h 50m
Southwest
Mon 8/3111:10 am
SAT
- MDW
2 stops5h 45m
Southwest
Deal found 7/10![Southwest logo]()
$349
This Southwest deal was found by Cheapflights users on 7/12. 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.
Mon 8/108:35 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Fri 8/142:15 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 7/12![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 7/11. 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 9/48:35 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Tue 9/83:35 pm
SAT
- MDW
1 stop4h 35m
Southwest
Deal found 7/11![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 7/9. 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 8/1510:05 am
MDW
- SAT
2 stops5h 55m
Southwest
Sun 8/166:50 am
SAT
- MDW
1 stop7h 15m
Southwest
Deal found 7/9![Southwest logo]()
$363
This Southwest deal was found by Cheapflights users on 7/8. 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 8/81:50 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Sat 8/1511:10 am
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 7/8![Southwest logo]()
$367
Last-minute flights from Midway to San AntonioDiscover last-minute flight deals from Midway to San Antonio. Data last updated July 13, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Antonio. Data last updated July 13, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/10. 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 8/48:30 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Tue 8/111:30 pm
SAT
- MDW
1 stop7h 10m
Southwest
Deal found 7/10![Southwest logo]()
$274
This Delta deal was found by Cheapflights users on 7/10. 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.
Tue 8/49:59 am
MDW
- SAT
1 stop7h 12m
Delta
Fri 8/75:15 am
SAT
- MDW
1 stop7h 24m
Delta
Deal found 7/10![Delta logo]()
$285
This Southwest deal was found by Cheapflights users on 7/8. 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 8/510:30 am
MDW
- SAT
2 stops6h 20m
Southwest
Wed 8/128:10 am
SAT
- MDW
1 stop6h 15m
Southwest
Deal found 7/8![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 7/8. 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 8/64:45 pm
MDW
- SAT
1 stop5h 40m
Southwest
Mon 8/103:30 pm
SAT
- MDW
1 stop3h 50m
Southwest
Deal found 7/8![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 7/9. 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 8/68:35 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Thu 8/135:00 am
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 7/9![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 7/10. 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 8/78:35 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Mon 8/103:30 pm
SAT
- MDW
1 stop3h 50m
Southwest
Deal found 7/10![Southwest logo]()
$271
This Southwest deal was found by Cheapflights users on 7/9. 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.
Mon 8/108:35 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Fri 8/146:10 pm
SAT
- MDW
1 stop5h 35m
Southwest
Deal found 7/9![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 7/8. 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 8/191:55 pm
MDW
- SAT
1 stop4h 00m
Southwest
Fri 8/213:30 pm
SAT
- MDW
1 stop3h 50m
Southwest
Deal found 7/8![Southwest logo]()
$277
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 July 13, 2026.
Search for one-way flight options from Midway to San Antonio. Find affordable one-way fares based on user searches. Data last updated July 13, 2026.
This Southwest deal was found by Cheapflights users on 7/12. 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.
Mon 8/108:35 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 7/12![Southwest logo]()
$149
This Southwest deal was found by Cheapflights users on 7/8. 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 8/1411:05 am
MDW
- SAT
Nonstop2h 35m
Southwest
Deal found 7/8![Southwest logo]()
$150
This Southwest deal was found by Cheapflights users on 7/11. 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 8/191:55 pm
MDW
- SAT
1 stop4h 00m
Southwest
Deal found 7/11![Southwest logo]()
$154
This Delta deal was found by Cheapflights users on 7/11. 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.
Thu 9/105:45 pm
MDW
- SAT
1 stop5h 01m
Delta
Deal found 7/11![Delta logo]()
$159
This Delta deal was found by Cheapflights users on 7/8. 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 8/79:24 am
MDW
- SAT
1 stop6h 30m
Delta
Deal found 7/8![Delta logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 8/1111:06 am
MDW
- SAT
2 stops31h 48m
Frontier
Deal found 7/9![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 8/412:11 pm
MDW
- SAT
2 stops30h 43m
Frontier
Deal found 7/9![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 7/9. 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.
Wed 8/56:05 am
MDW
- SAT
2 stops12h 49m
Frontier
Deal found 7/9![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 9/511:45 am
MDW
- SAT
2 stops21h 30m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 10/106:40 am
MDW
- SAT
2 stops26h 05m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 9/76:05 am
MDW
- SAT
2 stops37h 26m
Frontier
Deal found 7/9![Frontier logo]()
$170
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 July 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $271 (Southwest) |
One-way from | $149 (Southwest) |
Popular in | April |
Cheapest in | October |
Average price | $387 |
Good round-trip deal | $319 or less |
Good one-way deal | $145 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 2,558,603 searches. Data last updated July 13, 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
Quickest round-trip
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Tue 9/8
8:30 pm-11:10 pm
Nonstop2h 40m
San Antonio
Tue 9/15
9:25 am-12:00 pm
Nonstop2h 35m
$297
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Mon 8/24
8:35 pm-11:15 pm
Nonstop2h 40m
San Antonio
Mon 8/31
5:00 am-7:35 am
Nonstop2h 35m
$301
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Sat 10/10
11:35 am-5:15 pm
1 stop5h 40m
San Antonio
Thu 10/15
6:45 am-12:05 pm
1 stop5h 20m
$317
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Thu 8/6
4:45 pm-10:25 pm
1 stop5h 40m
San Antonio
Mon 8/10
11:10 am-4:55 pm
2 stops5h 45m
$324
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Thu 8/27
10:10 am-5:00 pm
2 stops6h 50m
San Antonio
Mon 8/31
11:10 am-4:55 pm
2 stops5h 45m
$349
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Mon 8/10
8:35 pm-11:15 pm
Nonstop2h 40m
San Antonio
Fri 8/14
2:15 pm-4:50 pm
Nonstop2h 35m
$352
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Sun 9/13
9:59 am-5:10 pm
1 stop7h 11m
San Antonio
Wed 9/16
10:59 am-4:16 pm
1 stop5h 17m
$359
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Fri 9/4
8:35 pm-11:15 pm
Nonstop2h 40m
San Antonio
Tue 9/8
3:35 pm-8:10 pm
1 stop4h 35m
$362
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Sat 8/15
10:05 am-4:00 pm
2 stops5h 55m
San Antonio
Sun 8/16
6:50 am-2:05 pm
1 stop7h 15m
$363
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Sat 8/8
1:50 pm-4:30 pm
Nonstop2h 40m
San Antonio
Sat 8/15
11:10 am-1:45 pm
Nonstop2h 35m
$367
Showing 1-10 of 22 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 July.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | 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 $235). Flying from Chicago Midway Airport to San Antonio in April is currently the most expensive (average of $594). 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 July 13, 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 28% 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 July 13, 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.
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Midway to San Antonio. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near San Antonio?
Book flights to San Antonio if you plan to visit one of these locationsNew Braunfels
Kerrville
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Top 2 airlines flying from Midway to San Antonio
Discover the top 2 airlines that operate flights from Midway to San Antonio. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$200 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$437 | FlexibilityNo cancel fee | On-time63% |