$111+ Cheap flights from Chicago (CHI) to San Antonio (SAT)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAT
Jul 21 — Jul 281
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 October or August, booked 47 days in advance, depart on a Tuesday or Wednesday and return on a Thursday
Cheap flight deals from Chicago to San Antonio
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Best
Last-minute
One-way
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 June 21, 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 June 21, 2026.
This Expedia deal was found by Cheapflights users on 6/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/79:57 pm
ORD
- SAT
1 stop20h 47m
Frontier
Sat 7/119:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/16![Frontier logo]()
$270
This Expedia deal was found by Cheapflights users on 6/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2311:06 am
ORD
- SAT
1 stop24h 15m
Frontier
Mon 10/2612:16 pm
SAT
- ORD
1 stop21h 45m
Frontier
Deal found 6/16![Frontier logo]()
$277
This Super.com deal was found by Cheapflights users on 6/16. 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 7/245:13 pm
ORD
- SAT
1 stop22h 28m
Frontier
Sun 7/269:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/16![Frontier logo]()
$278
This Booking.com deal was found by Cheapflights users on 6/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:15 am
ORD
- SAT
1 stop13h 22m
Frontier
Thu 7/237:39 pm
SAT
- ORD
1 stop25h 13m
Frontier
Deal found 6/17![Frontier logo]()
$281
This Frontier deal was found by Cheapflights users on 6/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:20 am
ORD
- SAT
1 stop12h 51m
Frontier
Wed 7/159:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/18![Frontier logo]()
$286
This Frontier deal was found by Cheapflights users on 6/19. 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.
Tue 7/217:15 am
ORD
- SAT
1 stop13h 22m
Frontier
Fri 7/249:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/19![Frontier logo]()
$287
This American Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:09 am
ORD
- SAT
1 stop5h 58m
American Airlines
Tue 9/296:48 pm
SAT
- ORD
Nonstop3h 12m
American Airlines
Deal found 6/20![American Airlines logo]()
$288
This Southwest deal was found by Cheapflights users on 6/19. 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 11/48:45 pm
MDW
- SAT
Nonstop2h 50m
Southwest
Mon 11/98:45 pm
SAT
- MDW
1 stop4h 20m
Southwest
Deal found 6/19![Southwest logo]()
$288
This CheapOair deal was found by Cheapflights users on 6/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/169:57 pm
ORD
- SAT
1 stop20h 47m
Frontier
Mon 7/209:51 am
SAT
- ORD
1 stop13h 19m
Frontier
Deal found 6/19![Frontier logo]()
$289
This Frontier deal was found by Cheapflights users on 6/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:15 am
ORD
- SAT
1 stop13h 22m
Frontier
Fri 7/109:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/18![Frontier logo]()
$290
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/148:52 am
ORD
- SAT
1 stop6h 59m
Delta
Sat 7/1812:24 pm
SAT
- ORD
1 stop8h 09m
Delta
Deal found 6/19![Delta logo]()
$291
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2611:25 am
MDW
- SAT
1 stop7h 13m
Delta
Wed 9/305:15 am
SAT
- MDW
1 stop7h 19m
Delta
Deal found 6/19![Delta logo]()
$291
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 June 21, 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 June 21, 2026.
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:45 am
MDW
- SAT
2 stops6h 50m
Southwest
Tue 8/42:35 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 6/17![Southwest logo]()
$312
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:45 am
ORD
- SAT
Nonstop3h 07m
United Airlines
Mon 9/75:59 pm
SAT
- ORD
1 stop7h 00m
United Airlines
Deal found 6/18![United Airlines logo]()
$323
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:30 am
ORD
- SAT
1 stop5h 40m
Delta
Mon 8/105:20 am
SAT
- ORD
1 stop7h 20m
Delta
Deal found 6/16![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 6/18. 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 8/274:30 pm
MDW
- SAT
1 stop5h 05m
Southwest
Thu 9/32:05 pm
SAT
- MDW
1 stop5h 25m
Southwest
Deal found 6/18![Southwest logo]()
$333
This United Airlines deal was found by Cheapflights users on 6/16. 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.
Tue 8/184:11 pm
ORD
- SAT
1 stop5h 05m
United Airlines
Fri 8/2112:55 pm
SAT
- ORD
Nonstop3h 00m
United Airlines
Deal found 6/16![United Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:40 am
ORD
- SAT
1 stop6h 58m
Delta
Fri 9/45:45 pm
SAT
- ORD
1 stop6h 12m
Delta
Deal found 6/19![Delta logo]()
$366
This Southwest deal was found by Cheapflights users on 6/15. 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.
Thu 7/309:25 pm
MDW
- SAT
Nonstop2h 45m
Southwest
Thu 8/65:00 am
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 6/15![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/185:05 am
MDW
- SAT
1 stop6h 45m
Southwest
Tue 7/212:00 pm
SAT
- MDW
Nonstop2h 40m
Southwest
Deal found 6/16![Southwest logo]()
$342
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/1310:48 am
MDW
- SAT
1 stop8h 00m
Delta
Wed 9/164:21 pm
SAT
- MDW
1 stop6h 24m
Delta
Deal found 6/20![Delta logo]()
$377
This United Airlines deal was found by Cheapflights users on 6/17. 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 9/18:45 am
ORD
- SAT
Nonstop3h 07m
United Airlines
Wed 9/25:27 pm
SAT
- ORD
Nonstop3h 00m
United Airlines
Deal found 6/17![United Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/810:05 am
MDW
- SAT
2 stops5h 55m
Southwest
Mon 8/103:30 pm
SAT
- MDW
1 stop3h 50m
Southwest
Deal found 6/20![Southwest logo]()
$347
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:45 am
ORD
- SAT
Nonstop3h 07m
United Airlines
Sun 8/165:59 pm
SAT
- ORD
1 stop5h 27m
United Airlines
Deal found 6/18![United Airlines logo]()
$388
This Southwest deal was found by Cheapflights users on 6/18. 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.
Fri 7/249:25 pm
MDW
- SAT
Nonstop2h 45m
Southwest
Tue 7/282:00 pm
SAT
- MDW
Nonstop2h 40m
Southwest
Deal found 6/18![Southwest logo]()
$352
This United Airlines deal was found by Cheapflights users on 6/16. 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 9/181:30 pm
ORD
- SAT
Nonstop3h 01m
United Airlines
Fri 10/22:00 pm
SAT
- ORD
Nonstop3h 00m
United Airlines
Deal found 6/16![United Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 6/17. 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.
Wed 7/16:00 am
ORD
- SAT
1 stop6h 43m
United Airlines
Sun 7/56:40 am
SAT
- ORD
Nonstop2h 58m
United Airlines
Deal found 6/17![United Airlines logo]()
$439
This Southwest deal was found by Cheapflights users on 6/16. 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.
Wed 7/810:25 am
MDW
- SAT
Nonstop2h 40m
Southwest
Sat 7/112:15 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 6/16![Southwest logo]()
$401
This United Airlines deal was found by Cheapflights users on 6/19. 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 7/47:58 pm
ORD
- SAT
Nonstop2h 59m
United Airlines
Tue 7/711:43 am
SAT
- ORD
1 stop4h 56m
United Airlines
Deal found 6/19![United Airlines logo]()
$441
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/79:00 pm
MDW
- SAT
Nonstop2h 45m
Southwest
Sat 7/1111:40 am
SAT
- MDW
2 stops5h 15m
Southwest
Deal found 6/16![Southwest logo]()
$412
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/43:35 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Tue 7/711:25 am
SAT
- MDW
2 stops5h 35m
Southwest
Deal found 6/17![Southwest logo]()
$420
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/257:58 pm
ORD
- SAT
Nonstop2h 59m
United Airlines
Sun 6/285:32 pm
SAT
- ORD
Nonstop3h 01m
United Airlines
Deal found 6/20![United Airlines logo]()
$561
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/132:30 pm
ORD
- SAT
2 stops8h 14m
United Airlines
Wed 9/165:30 am
SAT
- ORD
1 stop4h 45m
United Airlines
Deal found 6/20![United Airlines logo]()
$703
Last-minute flights from Chicago to San AntonioDiscover last-minute flight deals from Chicago to San Antonio. Data last updated June 21, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San Antonio. Data last updated June 21, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 6/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:20 am
ORD
- SAT
1 stop12h 51m
Frontier
Wed 7/159:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/18![Frontier logo]()
$286
This Booking.com deal was found by Cheapflights users on 6/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/259:48 pm
ORD
- SAT
1 stop21h 08m
Frontier
Wed 7/229:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/16![Frontier logo]()
$288
This CheapOair deal was found by Cheapflights users on 6/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/39:48 pm
ORD
- SAT
1 stop21h 08m
Frontier
Wed 7/89:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/17![Frontier logo]()
$280
This Expedia deal was found by Cheapflights users on 6/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/79:57 pm
ORD
- SAT
1 stop20h 47m
Frontier
Sat 7/119:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/16![Frontier logo]()
$270
This Frontier deal was found by Cheapflights users on 6/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:15 am
ORD
- SAT
1 stop13h 22m
Frontier
Fri 7/109:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/18![Frontier logo]()
$290
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/148:52 am
ORD
- SAT
1 stop6h 59m
Delta
Sat 7/1812:24 pm
SAT
- ORD
1 stop8h 09m
Delta
Deal found 6/19![Delta logo]()
$291
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/159:00 am
MDW
- SAT
1 stop6h 20m
Southwest
Sat 7/185:20 pm
SAT
- MDW
1 stop5h 55m
Southwest
Deal found 6/19![Southwest logo]()
$291
This Booking.com deal was found by Cheapflights users on 6/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:15 am
ORD
- SAT
1 stop13h 22m
Frontier
Thu 7/237:39 pm
SAT
- ORD
1 stop25h 13m
Frontier
Deal found 6/17![Frontier logo]()
$281
This CheapOair deal was found by Cheapflights users on 6/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/169:57 pm
ORD
- SAT
1 stop20h 47m
Frontier
Mon 7/209:51 am
SAT
- ORD
1 stop13h 19m
Frontier
Deal found 6/19![Frontier logo]()
$289
This Frontier deal was found by Cheapflights users on 6/19. 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.
Tue 7/217:15 am
ORD
- SAT
1 stop13h 22m
Frontier
Fri 7/249:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/19![Frontier logo]()
$287
This Super.com deal was found by Cheapflights users on 6/16. 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 7/245:13 pm
ORD
- SAT
1 stop22h 28m
Frontier
Sun 7/269:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/16![Frontier logo]()
$278
This Frontier deal was found by Cheapflights users on 6/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/307:15 am
ORD
- SAT
1 stop13h 22m
Frontier
Sun 8/29:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/18![Frontier logo]()
$296
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 June 21, 2026.
Search for one-way flight options from Chicago to San Antonio. Find affordable one-way fares based on user searches. Data last updated June 21, 2026.
This Frontier deal was found by Cheapflights users on 6/21. 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.
Wed 9/1610:40 pm
ORD
- SAT
1 stop11h 32m
Frontier
Deal found 6/21![Frontier logo]()
$111
This Trip.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:41 pm
ORD
- SAT
1 stop28h 13m
Frontier
Deal found 6/20![Frontier logo]()
$114
This CheapOair deal was found by Cheapflights users on 6/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1411:06 am
ORD
- SAT
1 stop27h 09m
Frontier
Deal found 6/17![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:41 pm
ORD
- SAT
1 stop28h 13m
Frontier
Deal found 6/20![Frontier logo]()
$118
This Super.com deal was found by Cheapflights users on 6/16. 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.
Tue 7/149:57 pm
ORD
- SAT
1 stop20h 47m
Frontier
Deal found 6/16![Frontier logo]()
$120
This Expedia deal was found by Cheapflights users on 6/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/159:57 pm
ORD
- SAT
1 stop20h 47m
Frontier
Deal found 6/18![Frontier logo]()
$123
This Frontier deal was found by Cheapflights users on 6/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:02 pm
ORD
- SAT
1 stop8h 37m
Frontier
Deal found 6/16![Frontier logo]()
$124
This Frontier deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:15 am
ORD
- SAT
1 stop13h 22m
Frontier
Deal found 6/20![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/219:57 pm
ORD
- SAT
1 stop20h 47m
Frontier
Deal found 6/20![Frontier logo]()
$128
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/107:15 am
ORD
- SAT
1 stop13h 22m
Frontier
Deal found 6/17![Frontier logo]()
$129
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:35 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 6/20![Southwest logo]()
$143
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:56 am
MDW
- SAT
1 stop5h 43m
Delta
Deal found 6/20![Delta logo]()
$146
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 June 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $270 (Expedia) |
One-way from | $111 (Frontier) |
Popular in | April |
Cheapest in | October |
Average price | $365 |
Good round-trip deal | $336 or less |
Good one-way deal | $183 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 2,558,603 searches. Data last updated June 21, 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 - SAT
MDWSAT
Chicago Midway
Tue 7/28
7:45 am-2:35 pm
2 stops6h 50m
San Antonio
Tue 8/4
2:35 pm-5:10 pm
Nonstop2h 35m
$312
ChicagoSan Antonio
ORD - SAT
ORDSAT
Chicago O'Hare Intl
Thu 9/3
8:45 am-11:52 am
Nonstop3h 07m
San Antonio
Mon 9/7
5:59 pm-12:59 am
1 stop7h 00m
$323
ChicagoSan Antonio
ORD - SAT
ORDSAT
Chicago O'Hare Intl
Thu 8/6
5:30 am-11:10 am
1 stop5h 40m
San Antonio
Mon 8/10
5:20 am-12:40 pm
1 stop7h 20m
$333
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Thu 8/27
4:30 pm-9:35 pm
1 stop5h 05m
San Antonio
Thu 9/3
2:05 pm-7:30 pm
1 stop5h 25m
$333
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Thu 7/30
9:25 pm-12:10 am
Nonstop2h 45m
San Antonio
Thu 8/6
5:00 am-7:35 am
Nonstop2h 35m
$340
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Sat 7/18
5:05 am-11:50 am
1 stop6h 45m
San Antonio
Tue 7/21
2:00 pm-4:40 pm
Nonstop2h 40m
$342
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Sat 8/8
10:05 am-4:00 pm
2 stops5h 55m
San Antonio
Mon 8/10
3:30 pm-7:20 pm
1 stop3h 50m
$347
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Fri 7/24
9:25 pm-12:10 am
Nonstop2h 45m
San Antonio
Tue 7/28
2:00 pm-4:40 pm
Nonstop2h 40m
$352
ChicagoSan Antonio
ORD - SAT
ORDSAT
Chicago O'Hare Intl
Tue 8/18
4:11 pm-9:16 pm
1 stop5h 05m
San Antonio
Fri 8/21
12:55 pm-3:55 pm
Nonstop3h 00m
$362
ChicagoSan Antonio
ORD - SAT
ORDSAT
Chicago O'Hare Intl
Mon 8/31
6:40 am-1:38 pm
1 stop6h 58m
San Antonio
Fri 9/4
5:45 pm-11:57 pm
1 stop6h 12m
$366
Showing 1-10 of 44 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 June.
| 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 Accuracy2 stars | Trust Score*3 stars | |
| 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 $88). Flying from Chicago to San Antonio in April is currently the most expensive (average of $207). 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 June 21, 2026.
It’s typically best to fly out from Chicago to San Antonio in the evening. Doing so could potentially save you 8% on the flight price compared to flying in the afternoon, 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 June 21, 2026.
The most flights from CHI to SAT are scheduled on a Friday (29 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (17 on average).
How much does it cost to fly round-trip from Chicago to San Antonio?
How far ahead should I book a flight from Chicago to San Antonio?
Booking 46 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 June 20, 2026.
Travelers seeking maximum savings on their Chicago to San Antonio flight should consider departing on Tuesday 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 June 21, 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.
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - 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 June 21, 2026.
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Explore flights to San Antonio departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 21, 2026.
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 2,558,603 searches. Data last updated June 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$101 | Average$230 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$218 | Average$413 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$235 | Average$437 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$241 | Average$423 | FlexibilityNo cancel fee | On-time71% |