$139+ Cheap flights from San Antonio (SAT) to Midway (MDW)
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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — MDW
Jun 19 — Jun 261
Round-trip
1 adult, Economy
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Find cheap flights from San Antonio to Midway 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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Best
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Cheapest flights from San Antonio to MidwayExplore the most affordable flight options available from San Antonio to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 20, 2026.
Explore the most affordable flight options available from San Antonio to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 20, 2026.
This Southwest deal was found by Cheapflights users on 5/15. 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 6/92:00 pm
SAT
- MDW
Nonstop2h 40m
Southwest
Tue 6/169:00 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/15![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 5/18. 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 6/99:20 am
SAT
- MDW
Nonstop2h 35m
Southwest
Wed 6/109:00 am
MDW
- SAT
1 stop6h 20m
Southwest
Deal found 5/18![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 5/17. 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 7/282:00 pm
SAT
- MDW
Nonstop2h 40m
Southwest
Thu 8/611:05 am
MDW
- SAT
Nonstop2h 35m
Southwest
Deal found 5/17![Southwest logo]()
$318
This Delta deal was found by Cheapflights users on 5/18. 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.
Wed 6/245:15 am
SAT
- MDW
1 stop7h 31m
Delta
Wed 7/156:00 am
MDW
- SAT
1 stop7h 32m
Delta
Deal found 5/18![Delta logo]()
$325
This Southwest deal was found by Cheapflights users on 5/17. 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 8/812:55 pm
SAT
- MDW
1 stop6h 15m
Southwest
Tue 8/1110:10 am
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/17![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 5/15. 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 11/77:00 am
SAT
- MDW
Nonstop2h 35m
Southwest
Mon 11/99:30 pm
MDW
- SAT
Nonstop2h 50m
Southwest
Deal found 5/15![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 5/15. 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 6/305:30 am
SAT
- MDW
2 stops6h 40m
Southwest
Wed 7/87:45 am
MDW
- SAT
2 stops6h 50m
Southwest
Deal found 5/15![Southwest logo]()
$335
This Southwest deal was found by Cheapflights users on 5/18. 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 7/96:25 am
SAT
- MDW
Nonstop2h 35m
Southwest
Wed 7/159:00 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/18![Southwest logo]()
$336
This Delta deal was found by Cheapflights users on 5/15. 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.
Wed 8/1911:29 am
SAT
- MDW
1 stop7h 04m
Delta
Mon 8/246:05 am
MDW
- SAT
1 stop5h 05m
Delta
Deal found 5/15![Delta logo]()
$338
Best flights from San Antonio to MidwayDiscover carefully curated flight deals from San Antonio to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 20, 2026.
Discover carefully curated flight deals from San Antonio to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 20, 2026.
This Southwest deal was found by Cheapflights users on 5/18. 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 7/96:25 am
SAT
- MDW
Nonstop2h 35m
Southwest
Wed 7/159:00 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/18![Southwest logo]()
$336
This Delta deal was found by Cheapflights users on 5/17. 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.
Mon 9/216:30 am
SAT
- MDW
1 stop6h 41m
Delta
Thu 9/246:00 am
MDW
- SAT
1 stop5h 10m
Delta
Deal found 5/17![Delta logo]()
$351
This Southwest deal was found by Cheapflights users on 5/19. 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 6/103:15 pm
SAT
- MDW
1 stop6h 20m
Southwest
Sat 7/188:30 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/19![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 5/17. 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 6/254:15 pm
SAT
- MDW
1 stop6h 02m
Delta
Tue 6/306:00 am
MDW
- SAT
1 stop7h 35m
Delta
Deal found 5/17![Delta logo]()
$356
This Southwest deal was found by Cheapflights users on 5/19. 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 7/292:00 pm
SAT
- MDW
Nonstop2h 40m
Southwest
Wed 7/299:00 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/19![Southwest logo]()
$350
This Delta deal was found by Cheapflights users on 5/19. 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 7/75:15 am
SAT
- MDW
1 stop7h 23m
Delta
Fri 7/109:49 am
MDW
- SAT
1 stop7h 22m
Delta
Deal found 5/19![Delta logo]()
$376
This Southwest deal was found by Cheapflights users on 5/19. 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 7/203:20 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Thu 7/239:25 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/19![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 5/17. 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 7/165:15 am
SAT
- MDW
1 stop7h 23m
Delta
Thu 7/239:19 am
MDW
- SAT
1 stop6h 29m
Delta
Deal found 5/17![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 5/16. 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 10/176:45 am
SAT
- MDW
2 stops8h 40m
Southwest
Mon 10/1910:15 am
MDW
- SAT
2 stops5h 50m
Southwest
Deal found 5/16![Southwest logo]()
$379
This Southwest deal was found by Cheapflights users on 5/19. 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 7/47:00 am
SAT
- MDW
Nonstop2h 35m
Southwest
Sat 7/117:40 am
MDW
- SAT
2 stops8h 20m
Southwest
Deal found 5/19![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 5/16. 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 8/157:35 am
SAT
- MDW
1 stop4h 15m
Southwest
Sat 8/152:25 pm
MDW
- SAT
1 stop5h 55m
Southwest
Deal found 5/16![Southwest logo]()
$389
Last-minute flights from San Antonio to MidwayDiscover last-minute flight deals from San Antonio to Midway. Data last updated May 20, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Midway. Data last updated May 20, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/18. 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 6/99:20 am
SAT
- MDW
Nonstop2h 35m
Southwest
Wed 6/109:00 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/18![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 5/18. 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 6/92:00 pm
SAT
- MDW
Nonstop2h 40m
Southwest
Tue 6/165:30 am
MDW
- SAT
1 stop5h 50m
Southwest
Deal found 5/18![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 5/19. 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 6/103:15 pm
SAT
- MDW
1 stop6h 20m
Southwest
Sat 7/188:30 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/19![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 5/17. 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 6/172:00 pm
SAT
- MDW
Nonstop2h 40m
Southwest
Wed 6/249:00 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/17![Southwest logo]()
$336
This Delta deal was found by Cheapflights users on 5/18. 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 6/235:25 am
SAT
- MDW
1 stop6h 40m
Delta
Mon 7/69:17 am
MDW
- SAT
1 stop6h 32m
Delta
Deal found 5/18![Delta logo]()
$356
This Delta deal was found by Cheapflights users on 5/18. 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.
Wed 6/245:15 am
SAT
- MDW
1 stop7h 31m
Delta
Wed 7/156:00 am
MDW
- SAT
1 stop7h 32m
Delta
Deal found 5/18![Delta logo]()
$325
This Southwest deal was found by Cheapflights users on 5/16. 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 6/305:30 am
SAT
- MDW
2 stops6h 40m
Southwest
Tue 7/77:45 am
MDW
- SAT
2 stops6h 50m
Southwest
Deal found 5/16![Southwest logo]()
$335
One-way flights from San Antonio to MidwaySearch for one-way flight options from San Antonio to Midway. Find affordable one-way fares based on user searches. Data last updated May 20, 2026.
Search for one-way flight options from San Antonio to Midway. Find affordable one-way fares based on user searches. Data last updated May 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 8/179:51 am
SAT
- MDW
2 stops25h 21m
Frontier
Deal found 5/20![Frontier logo]()
$139
This Southwest deal was found by Cheapflights users on 5/17. 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 7/142:00 pm
SAT
- MDW
Nonstop2h 40m
Southwest
Deal found 5/17![Southwest logo]()
$153
This Delta deal was found by Cheapflights users on 5/17. 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 7/145:20 am
SAT
- MDW
1 stop6h 36m
Delta
Deal found 5/17![Delta logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 8/104:26 pm
SAT
- MDW
2 stops29h 42m
Frontier
Deal found 5/17![Frontier logo]()
$164
This Southwest deal was found by Cheapflights users on 5/17. 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 8/135:00 am
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 5/17![Southwest logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 5/17. 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.
Sun 8/29:55 am
SAT
- MDW
2 stops25h 12m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 5/17. 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.
Sun 8/169:55 am
SAT
- MDW
2 stops49h 17m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 5/15. 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.
Fri 8/1411:30 am
SAT
- MDW
3 stops34h 38m
Multiple Airlines
Deal found 5/15![Multiple Airlines logo]()
$175
This Delta deal was found by Cheapflights users on 5/15. 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 8/1311:29 am
SAT
- MDW
1 stop7h 04m
Delta
Deal found 5/15![Delta logo]()
$176
This Southwest deal was found by Cheapflights users on 5/20. 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 8/158:35 am
SAT
- MDW
2 stops5h 40m
Southwest
Deal found 5/20![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 5/15. 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 6/296:25 am
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 5/15![Southwest logo]()
$184
Find flight deals from San Antonio to Midway
Discover tips and strategies to find the most affordable flight options for your journey from San Antonio (SAT) to Midway (MDW). 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 May 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $305 (Southwest) |
One-way from | $139 (Kiwi.com) |
Popular in | March |
Cheapest in | February |
Average price | $376 |
Good round-trip deal | $336 or less |
Good one-way deal | $208 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Antonio to Midway 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 May 20, 2026.
Use the filters below to find and compare flights from San Antonio to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Thu 7/9
6:25 am-9:00 am
Nonstop2h 35m
Chicago Midway
Wed 7/15
9:00 pm-11:40 pm
Nonstop2h 40m
$336
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Wed 6/10
3:15 pm-9:35 pm
1 stop6h 20m
Chicago Midway
Sat 7/18
8:30 pm-11:10 pm
Nonstop2h 40m
$346
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Wed 7/29
2:00 pm-4:40 pm
Nonstop2h 40m
Chicago Midway
Wed 7/29
9:00 pm-11:40 pm
Nonstop2h 40m
$350
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Mon 9/21
6:30 am-1:11 pm
1 stop6h 41m
Chicago Midway
Thu 9/24
6:00 am-11:10 am
1 stop5h 10m
$351
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Thu 6/25
4:15 pm-10:17 pm
1 stop6h 02m
Chicago Midway
Tue 6/30
6:00 am-1:35 pm
1 stop7h 35m
$356
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Mon 7/20
3:20 pm-5:55 pm
Nonstop2h 35m
Chicago Midway
Thu 7/23
9:25 pm-12:05 am
Nonstop2h 40m
$367
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Tue 7/7
5:15 am-12:38 pm
1 stop7h 23m
Chicago Midway
Fri 7/10
9:49 am-5:11 pm
1 stop7h 22m
$376
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Sat 10/17
6:45 am-3:25 pm
2 stops8h 40m
Chicago Midway
Mon 10/19
10:15 am-4:05 pm
2 stops5h 50m
$379
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Sat 7/4
7:00 am-9:35 am
Nonstop2h 35m
Chicago Midway
Sat 7/11
7:40 am-4:00 pm
2 stops8h 20m
$382
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Thu 7/16
5:15 am-12:38 pm
1 stop7h 23m
Chicago Midway
Thu 7/23
9:19 am-3:48 pm
1 stop6h 29m
$387
Showing 1-10 of 22 resultsSorted by cheapest first
Compare providers for flights from San Antonio to Midway
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 San Antonio to Midway in May.
| 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 | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on San Antonio-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Antonio-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Antonio-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Antonio-Chicago Midway Airport 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 San Antonio-Chicago Midway Airport 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 San Antonio to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from San Antonio with our price prediction graph.
SAT-MDW
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 San Antonio to Chicago Midway Airport
What is the cheapest time of day to fly from SAT to MDW?
Find hourly flight availability from San Antonio to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 20, 2026.
When flying from San Antonio to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How much does it cost to fly round-trip from San Antonio to Chicago Midway Airport?
The best insider tips for San Antonio to Chicago Midway Airport 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 San Antonio to Chicago Midway Airport trip
Our travel experts
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated May 20, 2026.
Read reviews from past customers who have flown Southwest and Frontier from San Antonio to Chicago Midway Airport. 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.
Boarding
8.1
Entertainment
7.5
Overall
7.9
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Entertainment
7.5
Overall
7.9
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Entertainment
7.5
Overall
7.9
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$222 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$256 | Average$406 | FlexibilityNo cancel fee | On-time63% |