$104+ Cheap flights from Chicago (CHI) to San Antonio (SAT)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAT
Nov 18 — Nov 251
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to San Antonio with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to San Antonio are usually found in September or June, booked 40 days in advance, depart on a Thursday or Saturday and return on a Thursday
Cheap flight deals from Chicago to San Antonio
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Best
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Cheapest flights from Chicago to San AntonioExplore the most affordable flight options available from Chicago to San Antonio. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 19, 2026.
Explore the most affordable flight options available from Chicago to San Antonio. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 19, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:30 am -
1 stop12h 55m
Fri 11/68:11 pm -
1 stop28h 10m
Deal found 10/15![Frontier logo]()
$305
This Southwest deal was found by Cheapflights users on 10/18. 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.
Wed 11/1810:15 am -
2 stops7h 25m
Thu 12/109:50 am -
2 stops7h 20m
Deal found 10/18![Southwest logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:30 am -
1 stop12h 55m
Tue 11/1710:29 pm -
2 stops20h 01m
Deal found 10/16![Frontier logo]()
$307
This Trip.com deal was found by Cheapflights users on 10/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:40 am -
1 stop12h 53m
Mon 11/2312:06 pm -
1 stop12h 37m
Deal found 10/16![Frontier logo]()
$308
This CheapOair deal was found by Cheapflights users on 10/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:30 am -
1 stop12h 55m
Sun 11/228:28 pm -
1 stop28h 25m
Deal found 10/15![Frontier logo]()
$309
This Super.com deal was found by Cheapflights users on 10/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:15 pm -
1 stop20h 34m
Fri 11/208:28 pm -
1 stop28h 25m
Deal found 10/16![Frontier logo]()
$310
This CheapOair deal was found by Cheapflights users on 10/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:35 am -
1 stop7h 07m
Sun 12/68:47 pm -
1 stop28h 07m
Deal found 10/15![Frontier logo]()
$313
This Cheapflightsfares deal was found by Cheapflights users on 10/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:30 am -
1 stop12h 55m
Fri 11/2012:06 pm -
1 stop27h 46m
Deal found 10/15![Frontier logo]()
$315
This Trip.com deal was found by Cheapflights users on 10/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:24 pm -
1 stop18h 55m
Sun 12/610:52 pm -
1 stop30h 09m
Deal found 10/18![Frontier logo]()
$316
This Cheapflightsfares deal was found by Cheapflights users on 10/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:40 am -
1 stop12h 53m
Mon 11/308:28 pm -
1 stop28h 25m
Deal found 10/17![Frontier logo]()
$317
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:30 am -
1 stop12h 55m
Wed 10/288:20 pm -
1 stop28h 01m
Deal found 10/16![Frontier logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:30 am -
1 stop12h 55m
Wed 11/2512:06 pm -
2 stops35h 12m
Deal found 10/19![Frontier logo]()
$320
Best flights from Chicago to San AntonioDiscover carefully curated flight deals from Chicago to San Antonio that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 19, 2026.
Discover carefully curated flight deals from Chicago to San Antonio that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 19, 2026.
This Southwest deal was found by Cheapflights users on 10/19. 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.
Thu 11/265:40 am -
1 stop4h 20m
Fri 11/2711:25 am -
1 stop4h 35m
Deal found 10/19![Southwest logo]()
$351
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/308:30 pm -
Nonstop3h 07m
Fri 12/44:57 pm -
1 stop7h 02m
Deal found 10/19![United Airlines logo]()
$406
This Mytrip deal was found by Cheapflights users on 10/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:30 am -
2 stops31h 19m
Mon 11/1610:29 pm -
2 stops25h 52m
Deal found 10/19![Frontier logo]()
$417
This Delta deal was found by Cheapflights users on 10/15. 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.
Mon 12/219:30 am -
1 stop5h 17m
Sat 12/264:50 pm -
1 stop5h 32m
Deal found 10/15![Delta logo]()
$420
This Southwest deal was found by Cheapflights users on 10/19. 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 12/199:40 pm -
Nonstop2h 55m
Mon 12/213:35 pm -
Nonstop2h 40m
Deal found 10/19![Southwest logo]()
$356
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/227:45 pm -
Nonstop3h 14m
Tue 12/296:45 am -
Nonstop2h 58m
Deal found 10/19![United Airlines logo]()
$424
This Southwest deal was found by Cheapflights users on 10/16. 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.
Mon 11/236:30 pm -
1 stop5h 40m
Fri 11/278:25 pm -
1 stop4h 45m
Deal found 10/16![Southwest logo]()
$415
This Delta deal was found by Cheapflights users on 10/17. 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 3/225:45 pm -
1 stop5h 35m
Thu 3/255:20 am -
1 stop7h 17m
Deal found 10/17![Delta logo]()
$457
This United Airlines deal was found by Cheapflights users on 10/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/179:00 am -
Nonstop3h 08m
Sat 11/211:15 pm -
Nonstop2h 58m
Deal found 10/17![United Airlines logo]()
$437
This Southwest deal was found by Cheapflights users on 10/19. 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 11/259:30 pm -
Nonstop3h 00m
Fri 11/278:25 pm -
1 stop4h 45m
Deal found 10/19![Southwest logo]()
$422
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/197:45 pm -
Nonstop3h 14m
Mon 12/211:54 pm -
Nonstop2h 58m
Deal found 10/19![United Airlines logo]()
$437
This Delta deal was found by Cheapflights users on 10/18. 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 12/237:00 am -
1 stop7h 47m
Wed 12/301:00 pm -
1 stop6h 59m
Deal found 10/18![Delta logo]()
$507
This Southwest deal was found by Cheapflights users on 10/15. 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 12/199:40 pm -
Nonstop2h 50m
Mon 12/286:25 am -
Nonstop2h 30m
Deal found 10/15![Southwest logo]()
$430
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/135:30 am -
1 stop5h 18m
Sat 1/166:38 am -
Nonstop2h 57m
Deal found 10/19![United Airlines logo]()
$447
This Southwest deal was found by Cheapflights users on 10/19. 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.
Fri 2/125:50 pm -
1 stop4h 55m
Mon 2/154:15 pm -
1 stop7h 15m
Deal found 10/19![Southwest logo]()
$432
This Delta deal was found by Cheapflights users on 10/18. 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.
Sun 11/226:49 am -
1 stop5h 50m
Sat 11/286:40 am -
1 stop5h 08m
Deal found 10/18![Delta logo]()
$545
This Southwest deal was found by Cheapflights users on 10/17. 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 11/198:50 pm -
Nonstop2h 55m
Mon 11/232:50 pm -
Nonstop2h 35m
Deal found 10/17![Southwest logo]()
$437
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:30 pm -
Nonstop3h 08m
Wed 11/2511:45 am -
1 stop6h 44m
Deal found 10/19![United Airlines logo]()
$485
This Southwest deal was found by Cheapflights users on 10/17. 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 2/1010:15 am -
1 stop4h 25m
Wed 2/171:45 pm -
Nonstop2h 30m
Deal found 10/17![Southwest logo]()
$443
This United Airlines deal was found by Cheapflights users on 10/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:55 am -
1 stop6h 21m
Sun 11/296:34 am -
Nonstop2h 59m
Deal found 10/16![United Airlines logo]()
$530
This United Airlines deal was found by Cheapflights users on 10/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:27 pm -
Nonstop3h 08m
Tue 11/101:15 pm -
Nonstop2h 58m
Deal found 10/16![United Airlines logo]()
$537
Last-minute flights from Chicago to San AntonioDiscover last-minute flight deals from Chicago to San Antonio. Data last updated October 19, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San Antonio. Data last updated October 19, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:30 am -
1 stop12h 55m
Wed 10/288:20 pm -
1 stop28h 01m
Deal found 10/16![Frontier logo]()
$318
This Trip.com deal was found by Cheapflights users on 10/14. 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.
Tue 11/36:30 am -
1 stop12h 55m
Sat 11/78:20 pm -
1 stop28h 01m
Deal found 10/14![Frontier logo]()
$314
This Cheapflightsfares deal was found by Cheapflights users on 10/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:30 am -
1 stop12h 55m
Fri 11/68:11 pm -
1 stop28h 10m
Deal found 10/15![Frontier logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:30 am -
1 stop12h 55m
Tue 11/1710:29 pm -
2 stops20h 01m
Deal found 10/16![Frontier logo]()
$307
This Super.com deal was found by Cheapflights users on 10/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:15 pm -
1 stop20h 34m
Fri 11/208:28 pm -
1 stop28h 25m
Deal found 10/16![Frontier logo]()
$310
This Trip.com deal was found by Cheapflights users on 10/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:30 am -
1 stop12h 44m
Sun 11/158:20 pm -
1 stop28h 01m
Deal found 10/17![Frontier logo]()
$316
This Cheapflightsfares deal was found by Cheapflights users on 10/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:30 am -
1 stop12h 55m
Fri 11/2012:06 pm -
1 stop27h 46m
Deal found 10/15![Frontier logo]()
$315
This Southwest deal was found by Cheapflights users on 10/18. 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.
Wed 11/1810:15 am -
2 stops7h 25m
Thu 12/109:50 am -
2 stops7h 20m
Deal found 10/18![Southwest logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:30 am -
1 stop12h 55m
Wed 11/2512:06 pm -
2 stops35h 12m
Deal found 10/19![Frontier logo]()
$320
This CheapOair deal was found by Cheapflights users on 10/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:30 am -
1 stop12h 55m
Sun 11/228:28 pm -
1 stop28h 25m
Deal found 10/15![Frontier logo]()
$309
This Trip.com deal was found by Cheapflights users on 10/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:40 am -
1 stop12h 53m
Mon 11/2312:06 pm -
1 stop12h 37m
Deal found 10/16![Frontier logo]()
$308
This Cheapflightsfares deal was found by Cheapflights users on 10/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:40 am -
1 stop12h 53m
Mon 11/308:28 pm -
1 stop28h 25m
Deal found 10/17![Frontier logo]()
$317
One-way flights from Chicago to San AntonioSearch for one-way flight options from Chicago to San Antonio. Find affordable one-way fares based on user searches. Data last updated October 19, 2026.
Search for one-way flight options from Chicago to San Antonio. Find affordable one-way fares based on user searches. Data last updated October 19, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:30 am -
1 stop12h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Frontier logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/197:35 am -
1 stop10h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 10/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:30 am -
1 stop12h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$114
This Mytrip deal was found by Cheapflights users on 10/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:30 am -
1 stop12h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Frontier logo]()
$117
This Frontier deal was found by Cheapflights users on 10/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:30 am -
1 stop12h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:21 am -
1 stop15h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$132
This Cheapflightsfares deal was found by Cheapflights users on 10/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:30 am -
1 stop12h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$134
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/217:52 pm -
Nonstop3h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![United Airlines logo]()
$137
This Southwest deal was found by Cheapflights users on 10/18. 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 12/38:50 pm -
Nonstop2h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Southwest logo]()
$138
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/208:35 pm -
1 stop15h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$146
This CheapOair deal was found by Cheapflights users on 10/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:40 am -
1 stop29h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$148
This Trip.com deal was found by Cheapflights users on 10/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:42 pm -
1 stop14h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$167
Find flight deals from Chicago to San Antonio
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 October 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $305 (Cheapflightsfares) |
One-way from | $104 (Cheapflightsfares) |
Popular in | August |
Cheapest in | September |
Average price | $419 |
Good round-trip deal | $313 or less |
Good one-way deal | $130 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to San Antonio that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 19, 2026.
Use the filters below to find and compare flights from Chicago to San Antonio that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Thu 12/3
10:15 am-5:40 pm
2 stops7h 25m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$153
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Sun 12/20
8:35 pm-12:32 pm
1 stop15h 57m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$154
ChicagoSan Antonio
ORD Chicago O'Hare Intl - SAT San Antonio
ORDSAT
Chicago O'Hare Intl
Fri 11/6
6:30 am-7:14 pm
1 stop12h 44m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$156
ChicagoSan Antonio
ORD Chicago O'Hare Intl - SAT San Antonio
ORDSAT
Chicago O'Hare Intl
Mon 12/14
9:05 am-12:20 pm
Nonstop3h 15m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$190
Quickest round-trip
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Sat 11/14
10:25 am-1:15 pm
Nonstop2h 50m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$190
ChicagoSan Antonio
ORD Chicago O'Hare Intl - SAT San Antonio
ORDSAT
Chicago O'Hare Intl
Sat 11/21
5:30 am-12:44 pm
1 stop7h 14m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$192
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Fri 11/13
5:13 pm-12:33 am
1 stop7h 20m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$200
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Wed 11/11
1:05 pm-7:48 pm
1 stop6h 43m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$200
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Thu 11/12
10:34 am-5:40 pm
1 stop7h 06m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$200
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Thu 11/12
10:15 am-5:25 pm
2 stops7h 10m
San Antonio
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$205
Showing 1-10 of 41 resultsSorted by cheapest first
Compare providers for flights from Chicago 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 Chicago to San Antonio in October.
| 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 | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-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-San Antonio flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-San Antonio flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-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-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 Chicago to San Antonio
Have a flexible travel schedule? Discover the best time to fly to San Antonio from Chicago with our price prediction graph.
CHI-SAT
ORD-SAT
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 to San Antonio
CHI-SAT
ORD-SAT
MDW-SAT
What is the cheapest month to book a flight from Chicago to San Antonio?
Currently, January is the cheapest month in which you can book a flight from Chicago to San Antonio (average of $361). Flying from Chicago to San Antonio in November is currently the most expensive (average of $438). 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 CHI to SAT?
Find hourly flight availability from Chicago 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 October 19, 2026.
It’s typically best to fly out from Chicago to San Antonio in the evening. Doing so could potentially save you 3% on the flight price compared to flying at noon, which is usually more expensive.
Weekly flight availability from Chicago to San Antonio
Explore weekly flight availability from Chicago to San Antonio. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 19, 2026.
The most flights from CHI to SAT are scheduled on a Friday (25 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (15 on average).
How much does it cost to fly round-trip from Chicago to San Antonio?
Airfare is below average for this route at the moment.
Chicago to San Antonio flights typically cost between $346 and $557 in November.The cheapest round-trip price found within the last 5 days was $305 on Frontier (Nov 4-Nov 6).
How far ahead should I book a flight from Chicago to San Antonio?
Booking 82 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San Antonio. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Chicago to San Antonio?
Use this chart to determine the cheapest time to fly round-trip from Chicago to San Antonio. Price data was last updated on October 17, 2026.
Travelers seeking maximum savings on their Chicago to San Antonio flight should consider departing on Friday afternoons when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Chicago 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 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 October 19, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Chicago to San Antonio. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago 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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Chicago and San Antonio flights
Browse other Chicago and San Antonio flight options. Last updated on October 19, 2026.
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Top 4 airlines flying from Chicago to San Antonio
Discover the top 4 airlines that operate flights from Chicago 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 7,457,451 searches. Data last updated October 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$101 | Average$235 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$257 | Average$441 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$277 | Average$441 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$277 | Average$431 | FlexibilityNo cancel fee | On-time71% |