$73+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — MDW
Mar 1 — Mar 81
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 January 30, 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 January 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Fri 2/278:22 pm
SAT
- MDW
2 stops18h 57m
Frontier
Mon 3/26:00 am
MDW
- SAT
1 stop10h 20m
Frontier
Deal found 1/29![Frontier logo]()
$190
This Frontier deal was found by Cheapflights users on 1/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/205:04 pm
SAT
- MDW
1 stop5h 21m
Frontier
Mon 2/236:00 am
MDW
- SAT
1 stop10h 18m
Frontier
Deal found 1/28![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/135:04 pm
SAT
- MDW
1 stop28h 04m
Frontier
Mon 2/166:00 am
MDW
- SAT
1 stop10h 18m
Frontier
Deal found 1/28![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Fri 2/206:00 am
SAT
- MDW
1 stop8h 26m
Multiple Airlines
Sun 2/229:04 pm
MDW
- SAT
1 stop19h 14m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/276:00 am
SAT
- MDW
1 stop8h 26m
Multiple Airlines
Fri 3/66:05 am
MDW
- SAT
1 stop8h 46m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2710:26 am
SAT
- MDW
2 stops12h 11m
Multiple Airlines
Sun 3/16:00 am
MDW
- SAT
1 stop10h 19m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/155:04 pm
SAT
- MDW
1 stop29h 25m
Frontier
Fri 2/206:00 am
MDW
- SAT
1 stop10h 15m
Frontier
Deal found 1/27![Frontier logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Tue 2/1710:26 am
SAT
- MDW
2 stops32h 41m
Multiple Airlines
Mon 2/236:00 am
MDW
- SAT
1 stop10h 18m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 4/77:45 am
SAT
- MDW
2 stops14h 34m
Frontier
Mon 4/136:00 am
MDW
- SAT
1 stop11h 05m
Frontier
Deal found 1/28![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Fri 2/208:22 pm
SAT
- MDW
2 stops18h 57m
Frontier
Sun 2/226:00 am
MDW
- SAT
1 stop10h 19m
Frontier
Deal found 1/29![Frontier logo]()
$245
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 January 30, 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 January 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/135:04 pm
SAT
- MDW
1 stop28h 04m
Frontier
Sun 2/156:00 am
MDW
- SAT
1 stop10h 19m
Frontier
Deal found 1/30![Frontier logo]()
$191
This Southwest deal was found by Cheapflights users on 1/30. 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 4/242:40 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Tue 4/289:00 pm
MDW
- SAT
Nonstop2h 50m
Southwest
Deal found 1/30![Southwest logo]()
$316
This Delta deal was found by Cheapflights users on 1/28. 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 4/16:13 am
SAT
- MDW
1 stop5h 49m
Delta
Sat 4/112:05 pm
MDW
- SAT
1 stop7h 42m
Delta
Deal found 1/28![Delta logo]()
$319
This Frontier deal was found by Cheapflights users on 1/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/205:04 pm
SAT
- MDW
1 stop5h 21m
Frontier
Sun 2/226:00 am
MDW
- SAT
1 stop10h 19m
Frontier
Deal found 1/30![Frontier logo]()
$250
This Delta deal was found by Cheapflights users on 1/28. 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 3/315:10 am
SAT
- MDW
1 stop7h 19m
Delta
Tue 4/76:07 pm
MDW
- SAT
1 stop6h 31m
Delta
Deal found 1/28![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 1/28. 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 3/194:05 pm
SAT
- MDW
1 stop6h 45m
Southwest
Sat 3/219:35 pm
MDW
- SAT
Nonstop2h 55m
Southwest
Deal found 1/28![Southwest logo]()
$326
This Expedia deal was found by Cheapflights users on 1/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/63:46 pm
SAT
- MDW
1 stop6h 33m
Frontier
Sun 3/88:00 am
MDW
- SAT
1 stop29h 23m
Frontier
Deal found 1/30![Frontier logo]()
$298
This Delta deal was found by Cheapflights users on 1/28. 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 4/16:13 am
SAT
- MDW
1 stop5h 49m
Delta
Tue 4/72:05 pm
MDW
- SAT
1 stop7h 42m
Delta
Deal found 1/28![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 1/28. 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 4/76:32 am
SAT
- MDW
1 stop6h 53m
Delta
Tue 4/76:07 pm
MDW
- SAT
1 stop6h 31m
Delta
Deal found 1/28![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 1/28. 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 3/316:13 am
SAT
- MDW
1 stop5h 49m
Delta
Wed 4/82:05 pm
MDW
- SAT
1 stop7h 42m
Delta
Deal found 1/28![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 1/28. 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 4/76:32 am
SAT
- MDW
1 stop6h 53m
Delta
Wed 4/812:47 pm
MDW
- SAT
1 stop5h 27m
Delta
Deal found 1/28![Delta logo]()
$319
Last-minute flights from San Antonio to MidwayDiscover last-minute flight deals from San Antonio to Midway. Data last updated January 30, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Midway. Data last updated January 30, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/135:04 pm
SAT
- MDW
1 stop28h 04m
Frontier
Mon 2/166:00 am
MDW
- SAT
1 stop10h 18m
Frontier
Deal found 1/28![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/155:04 pm
SAT
- MDW
1 stop29h 25m
Frontier
Fri 2/206:00 am
MDW
- SAT
1 stop10h 15m
Frontier
Deal found 1/27![Frontier logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Tue 2/1710:26 am
SAT
- MDW
2 stops32h 41m
Multiple Airlines
Mon 2/236:00 am
MDW
- SAT
1 stop10h 18m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/191:57 pm
SAT
- MDW
1 stop24h 29m
Multiple Airlines
Sat 2/216:00 am
MDW
- SAT
2 stops27h 30m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$259
This Frontier deal was found by Cheapflights users on 1/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/205:04 pm
SAT
- MDW
1 stop5h 21m
Frontier
Mon 2/236:00 am
MDW
- SAT
1 stop10h 18m
Frontier
Deal found 1/28![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Fri 2/206:00 am
SAT
- MDW
1 stop8h 26m
Multiple Airlines
Sun 2/229:04 pm
MDW
- SAT
1 stop19h 14m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Fri 2/208:22 pm
SAT
- MDW
2 stops18h 57m
Frontier
Sun 2/226:00 am
MDW
- SAT
1 stop10h 19m
Frontier
Deal found 1/29![Frontier logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Fri 2/278:22 pm
SAT
- MDW
2 stops18h 57m
Frontier
Mon 3/26:00 am
MDW
- SAT
1 stop10h 20m
Frontier
Deal found 1/29![Frontier logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/276:00 am
SAT
- MDW
1 stop8h 26m
Multiple Airlines
Fri 3/66:05 am
MDW
- SAT
1 stop8h 46m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2710:26 am
SAT
- MDW
2 stops12h 11m
Multiple Airlines
Sun 3/16:00 am
MDW
- SAT
1 stop10h 19m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$229
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 January 30, 2026.
Search for one-way flight options from San Antonio to Midway. Find affordable one-way fares based on user searches. Data last updated January 30, 2026.
This Super.com deal was found by Cheapflights users on 1/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/25:08 pm
SAT
- MDW
1 stop5h 21m
Frontier
Deal found 1/30![Frontier logo]()
$73
This Priceline deal was found by Cheapflights users on 1/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:04 pm
SAT
- MDW
1 stop5h 25m
Frontier
Deal found 1/29![Frontier logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/66:13 pm
SAT
- MDW
1 stop14h 30m
Frontier
Deal found 1/30![Frontier logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/165:04 pm
SAT
- MDW
1 stop26h 03m
Frontier
Deal found 1/30![Frontier logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/135:04 pm
SAT
- MDW
1 stop28h 04m
Frontier
Deal found 1/30![Frontier logo]()
$90
This WAYA deal was found by Cheapflights users on 1/29. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/275:04 pm
SAT
- MDW
1 stop5h 33m
Frontier
Deal found 1/29![Frontier logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/205:04 pm
SAT
- MDW
1 stop28h 29m
Frontier
Deal found 1/30![Frontier logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/2410:26 am
SAT
- MDW
2 stops32h 41m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2510:26 am
SAT
- MDW
2 stops29h 50m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$96
This WAYA deal was found by Cheapflights users on 1/28. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/63:46 pm
SAT
- MDW
1 stop6h 33m
Frontier
Deal found 1/28![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1710:26 am
SAT
- MDW
2 stops32h 41m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$104
This Trip.com deal was found by Cheapflights users on 1/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
SAT
- MDW
1 stop8h 55m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$106
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 January 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $190 (Kiwi.com) |
One-way from | $73 (Super.com) |
Popular in | November |
Cheapest in | September |
Average price | $376 |
Good round-trip deal | $347 or less |
Good one-way deal | $213 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 January 30, 2026.
Use the filters below to find and compare flights from San Antonio to Chicago Midway Airport that are best for you.
Fly from
San Antonio
Fly to
Midway
Route
Depart
Return
Price
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Fri 2/13
5:04 pm-9:08 pm
1 stop28h 04m
Chicago Midway
Sun 2/15
6:00 am-4:19 pm
1 stop10h 19m
$191
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Fri 2/20
5:04 pm-10:25 pm
1 stop5h 21m
Chicago Midway
Sun 2/22
6:00 am-4:19 pm
1 stop10h 19m
$250
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Fri 3/6
3:46 pm-10:19 pm
1 stop6h 33m
Chicago Midway
Sun 3/8
8:00 am-1:23 pm
1 stop29h 23m
$298
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Fri 4/24
2:40 pm-5:15 pm
Nonstop2h 35m
Chicago Midway
Tue 4/28
9:00 pm-11:50 pm
Nonstop2h 50m
$316
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Wed 4/1
6:13 am-12:02 pm
1 stop5h 49m
Chicago Midway
Sat 4/11
2:05 pm-9:47 pm
1 stop7h 42m
$319
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Tue 3/31
5:10 am-12:29 pm
1 stop7h 19m
Chicago Midway
Tue 4/7
6:07 pm-12:38 am
1 stop6h 31m
$319
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Wed 4/1
6:13 am-12:02 pm
1 stop5h 49m
Chicago Midway
Tue 4/7
2:05 pm-9:47 pm
1 stop7h 42m
$319
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Tue 4/7
6:32 am-1:25 pm
1 stop6h 53m
Chicago Midway
Tue 4/7
6:07 pm-12:38 am
1 stop6h 31m
$319
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Tue 3/31
6:13 am-12:02 pm
1 stop5h 49m
Chicago Midway
Wed 4/8
2:05 pm-9:47 pm
1 stop7h 42m
$319
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Tue 4/7
6:32 am-1:25 pm
1 stop6h 53m
Chicago Midway
Wed 4/8
12:47 pm-6:14 pm
1 stop5h 27m
$319
Showing 1-10 of 22 results
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 January.
| 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 month to book a flight from San Antonio to Chicago Midway Airport?
Currently, September is the cheapest month in which you can book a flight from San Antonio to Chicago Midway Airport (average of $138). Flying from San Antonio to Chicago Midway Airport in December is currently the most expensive (average of $277). 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 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 January 30, 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.
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 January 30, 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.
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentIla,Mar 2025
HOU - DAL
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentIla,Mar 2025
HOU - DAL
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentIla,Mar 2025
HOU - DAL
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Alternative routes for San Antonio to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Top 2 airlines flying from San Antonio to Midway
Discover the top 2 airlines 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 January 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$141 | Average$222 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$256 | Average$415 | FlexibilityNo cancel fee | On-time63% |