$133+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — MDW
Aug 3 — Aug 101
Round-trip
1 adult, Economy
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Find cheap flights from San Antonio to Midway 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
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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 July 4, 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 July 4, 2026.
This Southwest deal was found by Cheapflights users on 7/2. 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 8/183:35 pm
SAT
- MDW
1 stop4h 35m
Southwest
Tue 8/2510:30 am
MDW
- SAT
2 stops6h 20m
Southwest
Deal found 7/2![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 7/3. 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 8/189:25 am
SAT
- MDW
Nonstop2h 35m
Southwest
Wed 8/261:55 pm
MDW
- SAT
1 stop4h 00m
Southwest
Deal found 7/3![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 6/29. 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 8/103:30 pm
SAT
- MDW
1 stop3h 50m
Southwest
Sat 8/1510:05 am
MDW
- SAT
2 stops5h 55m
Southwest
Deal found 6/29![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 7/3. 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 8/81:10 pm
SAT
- MDW
1 stop7h 35m
Southwest
Sat 8/151:50 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 7/3![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 7/2. 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.
Mon 8/103:30 pm
SAT
- MDW
1 stop3h 50m
Southwest
Wed 8/1210:30 am
MDW
- SAT
2 stops6h 20m
Southwest
Deal found 7/2![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 7/2. 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 8/86:10 am
SAT
- MDW
2 stops8h 05m
Southwest
Tue 8/114:40 pm
MDW
- SAT
1 stop6h 15m
Southwest
Deal found 7/2![Southwest logo]()
$306
This Delta deal was found by Cheapflights users on 7/2. 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.
Mon 9/214:21 pm
SAT
- MDW
1 stop6h 24m
Delta
Thu 9/2410:48 am
MDW
- SAT
1 stop6h 15m
Delta
Deal found 7/2![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 7/2. 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 8/86:10 am
SAT
- MDW
2 stops8h 05m
Southwest
Mon 8/105:25 am
MDW
- SAT
1 stop5h 45m
Southwest
Deal found 7/2![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 7/2. 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 10/82:35 pm
SAT
- MDW
Nonstop2h 40m
Southwest
Tue 10/138:45 pm
MDW
- SAT
Nonstop2h 45m
Southwest
Deal found 7/2![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 6/29. 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 8/12:15 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Mon 8/108:35 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 6/29![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 6/29. 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 8/58:10 am
SAT
- MDW
1 stop6h 15m
Southwest
Sat 8/810:05 am
MDW
- SAT
2 stops5h 55m
Southwest
Deal found 6/29![Southwest logo]()
$330
This Southwest deal was found by Cheapflights users on 6/29. 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 8/14:40 pm
SAT
- MDW
1 stop6h 40m
Southwest
Sat 8/810:05 am
MDW
- SAT
2 stops5h 55m
Southwest
Deal found 6/29![Southwest logo]()
$333
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 July 4, 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 July 4, 2026.
This Southwest deal was found by Cheapflights users on 7/3. 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 8/189:25 am
SAT
- MDW
Nonstop2h 35m
Southwest
Wed 8/261:55 pm
MDW
- SAT
1 stop4h 00m
Southwest
Deal found 7/3![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 7/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/42:43 pm
SAT
- MDW
1 stop7h 53m
Delta
Tue 9/85:45 pm
MDW
- SAT
1 stop5h 01m
Delta
Deal found 7/3![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 7/3. 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.
Wed 8/199:20 am
SAT
- MDW
1 stop6h 00m
Southwest
Wed 8/2610:10 am
MDW
- SAT
2 stops5h 30m
Southwest
Deal found 7/3![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 6/30. 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 9/242:15 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Thu 9/248:35 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 6/30![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 7/1. 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.
Thu 9/33:25 pm
SAT
- MDW
1 stop4h 45m
Southwest
Mon 9/75:30 am
MDW
- SAT
1 stop5h 05m
Southwest
Deal found 7/1![Southwest logo]()
$349
This Southwest deal was found by Cheapflights users on 7/3. 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 9/33:30 pm
SAT
- MDW
1 stop3h 50m
Southwest
Sun 9/68:40 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 7/3![Southwest logo]()
$354
This Southwest deal was found by Cheapflights users on 7/2. 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 11/56:35 am
SAT
- MDW
1 stop5h 40m
Southwest
Sun 11/810:00 am
MDW
- SAT
Nonstop2h 50m
Southwest
Deal found 7/2![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 6/30. 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 8/203:30 pm
SAT
- MDW
1 stop3h 50m
Southwest
Sun 8/238:40 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 6/30![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 7/1. 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 7/255:20 pm
SAT
- MDW
1 stop5h 55m
Southwest
Mon 7/276:00 pm
MDW
- SAT
1 stop6h 25m
Southwest
Deal found 7/1![Southwest logo]()
$414
This Southwest deal was found by Cheapflights users on 6/29. 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 7/304:50 pm
SAT
- MDW
1 stop6h 15m
Southwest
Sun 8/25:25 am
MDW
- SAT
1 stop6h 30m
Southwest
Deal found 6/29![Southwest logo]()
$425
Last-minute flights from San Antonio to MidwayDiscover last-minute flight deals from San Antonio to Midway. Data last updated July 4, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Midway. Data last updated July 4, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/30. 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
Tue 8/48:30 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 6/30![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 6/29. 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 8/12:15 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Mon 8/108:35 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 6/29![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 6/29. 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 8/14:40 pm
SAT
- MDW
1 stop6h 40m
Southwest
Sat 8/810:05 am
MDW
- SAT
2 stops5h 55m
Southwest
Deal found 6/29![Southwest logo]()
$333
This Delta deal was found by Cheapflights users on 7/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/611:29 am
SAT
- MDW
1 stop7h 04m
Delta
Mon 8/101:51 pm
MDW
- SAT
1 stop7h 38m
Delta
Deal found 7/3![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 7/3. 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 8/81:10 pm
SAT
- MDW
1 stop7h 35m
Southwest
Sat 8/151:50 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 7/3![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 7/2. 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 8/86:10 am
SAT
- MDW
2 stops8h 05m
Southwest
Tue 8/114:40 pm
MDW
- SAT
1 stop6h 15m
Southwest
Deal found 7/2![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 7/2. 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 8/86:10 am
SAT
- MDW
2 stops8h 05m
Southwest
Mon 8/105:25 am
MDW
- SAT
1 stop5h 45m
Southwest
Deal found 7/2![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 6/29. 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 8/103:30 pm
SAT
- MDW
1 stop3h 50m
Southwest
Sat 8/1510:05 am
MDW
- SAT
2 stops5h 55m
Southwest
Deal found 6/29![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 7/2. 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.
Mon 8/103:30 pm
SAT
- MDW
1 stop3h 50m
Southwest
Wed 8/1210:30 am
MDW
- SAT
2 stops6h 20m
Southwest
Deal found 7/2![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 7/2. 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 8/183:35 pm
SAT
- MDW
1 stop4h 35m
Southwest
Tue 8/2510:30 am
MDW
- SAT
2 stops6h 20m
Southwest
Deal found 7/2![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 7/3. 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 8/189:25 am
SAT
- MDW
Nonstop2h 35m
Southwest
Wed 8/261:55 pm
MDW
- SAT
1 stop4h 00m
Southwest
Deal found 7/3![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 6/30. 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 8/285:00 am
SAT
- MDW
Nonstop2h 35m
Southwest
Wed 9/28:30 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 6/30![Southwest logo]()
$339
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 July 4, 2026.
Search for one-way flight options from San Antonio to Midway. Find affordable one-way fares based on user searches. Data last updated July 4, 2026.
This Southwest deal was found by Cheapflights users on 6/29. 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 9/92:50 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 6/29![Southwest logo]()
$133
This Southwest deal was found by Cheapflights users on 7/1. 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.
Tue 10/208:55 am
SAT
- MDW
Nonstop2h 40m
Southwest
Deal found 7/1![Southwest logo]()
$136
This Delta deal was found by Cheapflights users on 7/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:05 am
SAT
- MDW
1 stop7h 04m
Delta
Deal found 7/3![Delta logo]()
$146
This Southwest deal was found by Cheapflights users on 6/30. 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 7/285:30 am
SAT
- MDW
2 stops6h 40m
Southwest
Deal found 6/30![Southwest logo]()
$151
This Delta deal was found by Cheapflights users on 7/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:55 am
SAT
- MDW
1 stop7h 49m
Delta
Deal found 7/3![Delta logo]()
$156
This Southwest deal was found by Cheapflights users on 6/30. 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 9/2811:10 am
SAT
- MDW
2 stops5h 45m
Southwest
Deal found 6/30![Southwest logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 10/2012:16 pm
SAT
- MDW
2 stops22h 42m
Frontier
Deal found 7/1![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 9/2812:38 pm
SAT
- MDW
3 stops33h 20m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$182
This Southwest deal was found by Cheapflights users on 7/1. 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.
Thu 9/172:15 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 7/1![Southwest logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
Fri 8/2811:30 am
SAT
- MDW
3 stops35h 17m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
Mon 8/3111:30 am
SAT
- MDW
3 stops23h 25m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$186
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 July 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $296 (Southwest) |
One-way from | $133 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $517 |
Good round-trip deal | $352 or less |
Good one-way deal | $252 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 July 4, 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
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Tue 8/18
9:25 am-12:00 pm
Nonstop2h 35m
Chicago Midway
Wed 8/26
1:55 pm-5:55 pm
1 stop4h 00m
$297
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Wed 8/19
9:20 am-3:20 pm
1 stop6h 00m
Chicago Midway
Wed 8/26
10:10 am-3:40 pm
2 stops5h 30m
$316
Quickest round-trip
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Thu 9/24
2:15 pm-4:50 pm
Nonstop2h 35m
Chicago Midway
Thu 9/24
8:35 pm-11:15 pm
Nonstop2h 40m
$329
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Thu 9/3
3:25 pm-8:10 pm
1 stop4h 45m
Chicago Midway
Mon 9/7
5:30 am-10:35 am
1 stop5h 05m
$349
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Thu 9/3
3:30 pm-7:20 pm
1 stop3h 50m
Chicago Midway
Sun 9/6
8:40 pm-11:20 pm
Nonstop2h 40m
$354
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Fri 9/4
2:43 pm-10:36 pm
1 stop7h 53m
Chicago Midway
Tue 9/8
5:45 pm-10:46 pm
1 stop5h 01m
$369
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Thu 11/5
6:35 am-12:15 pm
1 stop5h 40m
Chicago Midway
Sun 11/8
10:00 am-12:50 pm
Nonstop2h 50m
$373
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Thu 8/20
3:30 pm-7:20 pm
1 stop3h 50m
Chicago Midway
Sun 8/23
8:40 pm-11:20 pm
Nonstop2h 40m
$373
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Sat 7/25
5:20 pm-11:15 pm
1 stop5h 55m
Chicago Midway
Mon 7/27
6:00 pm-12:25 am
1 stop6h 25m
$414
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Thu 7/30
4:50 pm-11:05 pm
1 stop6h 15m
Chicago Midway
Sun 8/2
5:25 am-11:55 am
1 stop6h 30m
$425
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 July.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | 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 July 4, 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 July 4, 2026.
Read reviews from past customers who have flown Southwest 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
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from San Antonio to Midway. 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 Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter
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Top airline flying from San Antonio to Midway
Discover the top airline that operate flights from San Antonio to Midway. 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 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$256 | Average$420 | FlexibilityNo cancel fee | On-time63% |