$124+ Cheap flights from San Antonio (SAT) to Chicago (CHI)
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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — CHI
Aug 22 — Aug 291
Round-trip
1 adult, Economy
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Find cheap flights from San Antonio to Chicago 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 San Antonio to Chicago are usually found in September or February, booked 26 days in advance, depart on a Thursday or Friday and return on a Tuesday
Cheap flight deals from San Antonio to Chicago
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Cheapest flights from San Antonio to ChicagoExplore the most affordable flight options available from San Antonio to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 23, 2026.
Explore the most affordable flight options available from San Antonio to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 23, 2026.
This Super.com deal was found by Cheapflights users on 7/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Wed 8/192:41 pm
ORD
- SAT
1 stop28h 50m
Frontier
Deal found 7/21![Frontier logo]()
$267
This CheapOair deal was found by Cheapflights users on 7/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/159:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Tue 8/182:41 pm
ORD
- SAT
1 stop28h 50m
Frontier
Deal found 7/21![Frontier logo]()
$268
This CheapOair deal was found by Cheapflights users on 7/23. 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 9/88:26 pm
SAT
- ORD
1 stop13h 35m
Frontier
Sat 9/1210:40 pm
ORD
- SAT
1 stop11h 32m
Frontier
Deal found 7/23![Frontier logo]()
$269
This Trip.com deal was found by Cheapflights users on 7/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:24 pm
SAT
- ORD
1 stop20h 38m
Frontier
Mon 8/248:11 pm
ORD
- SAT
1 stop25h 18m
Frontier
Deal found 7/19![Frontier logo]()
$271
This Super.com deal was found by Cheapflights users on 7/23. 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 9/88:26 pm
SAT
- ORD
1 stop25h 09m
Frontier
Sat 9/1910:40 pm
ORD
- SAT
1 stop11h 32m
Frontier
Deal found 7/23![Frontier logo]()
$272
This CheapOair deal was found by Cheapflights users on 7/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/289:51 am
SAT
- ORD
1 stop13h 17m
Frontier
Wed 9/22:41 pm
ORD
- SAT
1 stop28h 50m
Frontier
Deal found 7/21![Frontier logo]()
$273
This Frontier deal was found by Cheapflights users on 7/19. 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.
Sun 9/2010:34 pm
SAT
- ORD
1 stop13h 23m
Frontier
Thu 10/110:40 pm
ORD
- SAT
1 stop11h 32m
Frontier
Deal found 7/19![Frontier logo]()
$276
This Super.com deal was found by Cheapflights users on 7/23. 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.
Thu 8/2010:24 pm
SAT
- ORD
1 stop20h 38m
Frontier
Thu 8/272:41 pm
ORD
- SAT
1 stop28h 50m
Frontier
Deal found 7/23![Frontier logo]()
$277
This Frontier deal was found by Cheapflights users on 7/22. 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 8/219:51 am
SAT
- ORD
1 stop13h 17m
Frontier
Fri 8/289:10 pm
ORD
- SAT
1 stop11h 46m
Frontier
Deal found 7/22![Frontier logo]()
$278
This Super.com deal was found by Cheapflights users on 7/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:26 pm
SAT
- ORD
1 stop17h 10m
Frontier
Tue 8/252:41 pm
ORD
- SAT
1 stop28h 50m
Frontier
Deal found 7/20![Frontier logo]()
$279
This Frontier deal was found by Cheapflights users on 7/21. 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.
Fri 8/149:51 am
SAT
- ORD
1 stop13h 19m
Frontier
Mon 8/177:29 am
ORD
- SAT
1 stop13h 08m
Frontier
Deal found 7/21![Frontier logo]()
$283
This Frontier deal was found by Cheapflights users on 7/21. 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.
Sat 8/89:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Sat 8/157:29 am
ORD
- SAT
1 stop13h 08m
Frontier
Deal found 7/21![Frontier logo]()
$284
Best flights from San Antonio to ChicagoDiscover carefully curated flight deals from San Antonio to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 23, 2026.
Discover carefully curated flight deals from San Antonio to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 23, 2026.
This United Airlines deal was found by Cheapflights users on 7/23. 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 10/226:35 am
SAT
- ORD
Nonstop3h 00m
United Airlines
Mon 10/267:52 pm
ORD
- SAT
Nonstop3h 06m
United Airlines
Deal found 7/23![United Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 7/19. 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.
Tue 9/19:25 am
SAT
- MDW
Nonstop2h 35m
Southwest
Tue 9/18:30 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 7/19![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 7/19. 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 9/214:21 pm
SAT
- MDW
1 stop6h 23m
Delta
Thu 9/2410:48 am
MDW
- SAT
1 stop6h 13m
Delta
Deal found 7/19![Delta logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:32 pm
SAT
- RFD
1 stop15h 02m
Multiple Airlines
Fri 8/146:26 pm
RFD
- SAT
1 stop21h 15m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$428
This United Airlines deal was found by Cheapflights users on 7/23. 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 10/296:43 am
SAT
- ORD
Nonstop2h 56m
United Airlines
Mon 11/24:00 pm
ORD
- SAT
1 stop6h 51m
United Airlines
Deal found 7/23![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 7/19. 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 8/1512:55 pm
SAT
- MDW
1 stop6h 15m
Southwest
Sat 8/2210:05 am
MDW
- SAT
2 stops5h 55m
Southwest
Deal found 7/19![Southwest logo]()
$338
This United Airlines deal was found by Cheapflights users on 7/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:30 am
SAT
- ORD
1 stop4h 41m
United Airlines
Sat 10/315:45 pm
ORD
- SAT
1 stop5h 06m
United Airlines
Deal found 7/21![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 7/23. 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 9/106:10 pm
SAT
- ORD
1 stop5h 49m
Delta
Mon 9/145:10 pm
ORD
- SAT
1 stop5h 34m
Delta
Deal found 7/23![Delta logo]()
$357
This United Airlines deal was found by Cheapflights users on 7/18. 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 9/35:59 pm
SAT
- ORD
1 stop7h 00m
United Airlines
Mon 9/71:30 pm
ORD
- SAT
Nonstop3h 01m
United Airlines
Deal found 7/18![United Airlines logo]()
$323
This Delta deal was found by Cheapflights users on 7/19. 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.
Thu 9/311:29 am
SAT
- ORD
1 stop7h 00m
Delta
Tue 9/88:55 am
ORD
- SAT
1 stop6h 58m
Delta
Deal found 7/19![Delta logo]()
$360
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:20 pm
SAT
- MDW
1 stop5h 15m
Southwest
Sun 10/49:25 pm
MDW
- SAT
Nonstop2h 45m
Southwest
Deal found 7/23![Southwest logo]()
$385
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/411:29 am
SAT
- MDW
1 stop7h 04m
Delta
Tue 9/85:37 pm
MDW
- SAT
1 stop5h 07m
Delta
Deal found 7/22![Delta logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 7/18. 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.
Wed 8/59:32 pm
SAT
- RFD
1 stop15h 02m
Multiple Airlines
Sun 8/99:21 am
RFD
- SAT
2 stops23h 35m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$480
This Southwest deal was found by Cheapflights users on 7/19. 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 8/132:15 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Sun 8/168:40 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 7/19![Southwest logo]()
$415
This Delta deal was found by Cheapflights users on 7/18. 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.
Fri 12/184:25 pm
SAT
- ORD
1 stop7h 25m
Delta
Mon 12/215:55 pm
ORD
- SAT
1 stop6h 33m
Delta
Deal found 7/18![Delta logo]()
$380
This United Airlines deal was found by Cheapflights users on 7/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/254:18 pm
SAT
- ORD
1 stop6h 52m
United Airlines
Sat 1/27:45 pm
ORD
- SAT
Nonstop3h 15m
United Airlines
Deal found 7/21![United Airlines logo]()
$407
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:50 am
SAT
- MDW
1 stop6h 40m
Southwest
Fri 8/148:35 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 7/21![Southwest logo]()
$417
This Delta deal was found by Cheapflights users on 7/19. 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.
Fri 9/42:22 pm
SAT
- ORD
1 stop5h 08m
Delta
Tue 9/88:55 am
ORD
- SAT
1 stop6h 58m
Delta
Deal found 7/19![Delta logo]()
$380
This United Airlines deal was found by Cheapflights users on 7/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:55 pm
SAT
- ORD
Nonstop3h 00m
United Airlines
Fri 8/147:50 pm
ORD
- SAT
Nonstop3h 01m
United Airlines
Deal found 7/21![United Airlines logo]()
$407
This Kiwi.com deal was found by Cheapflights users on 7/18. 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.
Thu 8/69:55 am
SAT
- RFD
2 stops21h 54m
Multiple Airlines
Sun 8/91:24 pm
RFD
- SAT
1 stop31h 13m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$550
This Delta deal was found by Cheapflights users on 7/19. 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.
Thu 9/311:29 am
SAT
- MDW
1 stop7h 04m
Delta
Sun 9/66:05 am
MDW
- SAT
1 stop7h 33m
Delta
Deal found 7/19![Delta logo]()
$390
This Southwest deal was found by Cheapflights users on 7/18. 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 8/63:30 pm
SAT
- MDW
1 stop3h 50m
Southwest
Mon 8/108:35 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 7/18![Southwest logo]()
$439
This Delta deal was found by Cheapflights users on 7/22. 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 10/105:00 pm
SAT
- MDW
1 stop5h 25m
Delta
Sun 10/1110:58 am
MDW
- SAT
1 stop6h 17m
Delta
Deal found 7/22![Delta logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1012:16 pm
SAT
- RFD
2 stops24h 06m
Multiple Airlines
Sun 10/119:33 pm
RFD
- SAT
1 stop14h 15m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$590
This Delta deal was found by Cheapflights users on 7/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/102:30 pm
SAT
- ORD
1 stop7h 02m
Delta
Sun 10/116:30 am
ORD
- SAT
1 stop5h 14m
Delta
Deal found 7/21![Delta logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 11/2111:53 pm
SAT
- RFD
1 stop11h 54m
Multiple Airlines
Tue 11/2412:22 pm
RFD
- SAT
1 stop10h 36m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$690
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Fri 12/1812:38 pm
SAT
- RFD
2 stops22h 21m
Multiple Airlines
Tue 12/299:02 pm
RFD
- SAT
1 stop23h 24m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$744
Last-minute flights from San Antonio to ChicagoDiscover last-minute flight deals from San Antonio to Chicago. Data last updated July 23, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Chicago. Data last updated July 23, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 7/21. 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.
Sat 8/89:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Sat 8/157:29 am
ORD
- SAT
1 stop13h 08m
Frontier
Deal found 7/21![Frontier logo]()
$284
This Super.com deal was found by Cheapflights users on 7/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Wed 8/192:41 pm
ORD
- SAT
1 stop28h 50m
Frontier
Deal found 7/21![Frontier logo]()
$267
This Trip.com deal was found by Cheapflights users on 7/20. 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.
Wed 8/129:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Tue 8/182:41 pm
ORD
- SAT
1 stop28h 50m
Frontier
Deal found 7/20![Frontier logo]()
$276
This Frontier deal was found by Cheapflights users on 7/21. 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.
Fri 8/149:51 am
SAT
- ORD
1 stop13h 19m
Frontier
Mon 8/177:29 am
ORD
- SAT
1 stop13h 08m
Frontier
Deal found 7/21![Frontier logo]()
$283
This CheapOair deal was found by Cheapflights users on 7/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/159:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Tue 8/182:41 pm
ORD
- SAT
1 stop28h 50m
Frontier
Deal found 7/21![Frontier logo]()
$268
This Trip.com deal was found by Cheapflights users on 7/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:24 pm
SAT
- ORD
1 stop20h 38m
Frontier
Mon 8/248:11 pm
ORD
- SAT
1 stop25h 18m
Frontier
Deal found 7/19![Frontier logo]()
$271
This Super.com deal was found by Cheapflights users on 7/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:24 pm
SAT
- ORD
1 stop20h 38m
Frontier
Sun 8/237:44 pm
ORD
- SAT
1 stop13h 12m
Frontier
Deal found 7/20![Frontier logo]()
$285
This Super.com deal was found by Cheapflights users on 7/23. 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.
Thu 8/2010:24 pm
SAT
- ORD
1 stop20h 38m
Frontier
Thu 8/272:41 pm
ORD
- SAT
1 stop28h 50m
Frontier
Deal found 7/23![Frontier logo]()
$277
This CheapOair deal was found by Cheapflights users on 7/19. 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 8/2010:24 pm
SAT
- ORD
1 stop20h 38m
Frontier
Sun 8/308:11 pm
ORD
- SAT
1 stop25h 18m
Frontier
Deal found 7/19![Frontier logo]()
$286
This Frontier deal was found by Cheapflights users on 7/22. 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 8/219:51 am
SAT
- ORD
1 stop13h 17m
Frontier
Fri 8/289:10 pm
ORD
- SAT
1 stop11h 46m
Frontier
Deal found 7/22![Frontier logo]()
$278
This Super.com deal was found by Cheapflights users on 7/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:26 pm
SAT
- ORD
1 stop17h 10m
Frontier
Tue 8/252:41 pm
ORD
- SAT
1 stop28h 50m
Frontier
Deal found 7/20![Frontier logo]()
$279
This CheapOair deal was found by Cheapflights users on 7/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/289:51 am
SAT
- ORD
1 stop13h 17m
Frontier
Wed 9/22:41 pm
ORD
- SAT
1 stop28h 50m
Frontier
Deal found 7/21![Frontier logo]()
$273
One-way flights from San Antonio to ChicagoSearch for one-way flight options from San Antonio to Chicago. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
Search for one-way flight options from San Antonio to Chicago. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
This Frontier deal was found by Cheapflights users on 7/19. 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.
Sat 9/198:37 pm
SAT
- ORD
1 stop9h 05m
Frontier
Deal found 7/19![Frontier logo]()
$124
This Super.com deal was found by Cheapflights users on 7/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:26 pm
SAT
- ORD
1 stop17h 10m
Frontier
Deal found 7/19![Frontier logo]()
$128
This Frontier deal was found by Cheapflights users on 7/20. 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.
Mon 8/179:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 7/20![Frontier logo]()
$129
This Frontier deal was found by Cheapflights users on 7/22. 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 8/229:51 am
SAT
- ORD
1 stop13h 17m
Frontier
Deal found 7/22![Frontier logo]()
$130
This Trip.com deal was found by Cheapflights users on 7/22. 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 8/139:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 7/22![Frontier logo]()
$132
This Super.com deal was found by Cheapflights users on 7/22. 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 8/218:26 pm
SAT
- ORD
1 stop17h 10m
Frontier
Deal found 7/22![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Sat 8/159:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 7/19![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Tue 10/2012:16 pm
SAT
- ORD
1 stop21h 45m
Frontier
Deal found 7/19![Frontier logo]()
$148
This United Airlines deal was found by Cheapflights users on 7/22. 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 9/221:00 pm
SAT
- ORD
Nonstop3h 00m
United Airlines
Deal found 7/22![United Airlines logo]()
$149
This Southwest deal was found by Cheapflights users on 7/22. 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 9/229:25 am
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 7/22![Southwest logo]()
$149
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/213:30 pm
SAT
- MDW
1 stop3h 50m
Southwest
Deal found 7/22![Southwest logo]()
$154
This Southwest deal was found by Cheapflights users on 7/18. 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.
Mon 8/105:00 am
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 7/18![Southwest logo]()
$157
Find flight deals from San Antonio to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San Antonio (SAT) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $267 (Super.com) |
One-way from | $124 (Frontier) |
Popular in | June |
Cheapest in | September |
Average price | $393 |
Good round-trip deal | $338 or less |
Good one-way deal | $252 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Antonio to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 23, 2026.
Use the filters below to find and compare flights from San Antonio to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Thu 10/22
6:35 am-9:35 am
Nonstop3h 00m
Chicago O'Hare Intl
Mon 10/26
7:52 pm-10:58 pm
Nonstop3h 06m
$297
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Thu 10/29
6:43 am-9:39 am
Nonstop2h 56m
Chicago O'Hare Intl
Mon 11/2
4:00 pm-10:51 pm
1 stop6h 51m
$307
Quickest round-trip
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Tue 9/1
9:25 am-12:00 pm
Nonstop2h 35m
Chicago Midway
Tue 9/1
8:30 pm-11:10 pm
Nonstop2h 40m
$313
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Wed 10/28
5:30 am-10:11 am
1 stop4h 41m
Chicago O'Hare Intl
Sat 10/31
5:45 pm-10:51 pm
1 stop5h 06m
$317
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Thu 9/3
5:59 pm-12:59 am
1 stop7h 00m
Chicago O'Hare Intl
Mon 9/7
1:30 pm-4:31 pm
Nonstop3h 01m
$323
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Mon 9/21
4:21 pm-10:44 pm
1 stop6h 23m
Chicago Midway
Thu 9/24
10:48 am-5:01 pm
1 stop6h 13m
$333
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Sat 8/15
12:55 pm-7:10 pm
1 stop6h 15m
Chicago Midway
Sat 8/22
10:05 am-4:00 pm
2 stops5h 55m
$338
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Thu 9/10
6:10 pm-11:59 pm
1 stop5h 49m
Chicago O'Hare Intl
Mon 9/14
5:10 pm-10:44 pm
1 stop5h 34m
$357
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Thu 9/3
11:29 am-6:29 pm
1 stop7h 00m
Chicago O'Hare Intl
Tue 9/8
8:55 am-3:53 pm
1 stop6h 58m
$360
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Fri 9/4
11:29 am-6:33 pm
1 stop7h 04m
Chicago Midway
Tue 9/8
5:37 pm-10:44 pm
1 stop5h 07m
$377
Showing 1-10 of 54 resultsSorted by cheapest first
Compare providers for flights from San Antonio to Chicago
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 Chicago in July.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San Antonio-Chicago 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 flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Antonio-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Antonio-Chicago 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 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 Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San Antonio with our price prediction graph.
SAT-CHI
SAT-ORD
SAT-MDW
SAT-RFD
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
SAT-CHI
SAT-ORD
SAT-MDW
SAT-RFD
What is the cheapest month to book a flight from San Antonio to Chicago?
Currently, September is the cheapest month in which you can book a flight from San Antonio to Chicago (average of $324). Flying from San Antonio to Chicago in June is currently the most expensive (average of $445). 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 CHI?
Find hourly flight availability from San Antonio to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 23, 2026.
When flying from San Antonio to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 34% versus a flight at noon.
Weekly flight availability from San Antonio to Chicago
Explore weekly flight availability from San Antonio to Chicago. 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 July 23, 2026.
The most flights from SAT to CHI are scheduled on a Wednesday (30 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 on average).
How much does it cost to fly round-trip from San Antonio to Chicago?
Airfare is below average for this route at the moment.
San Antonio to Chicago flights typically cost between $306 and $470 in August.The cheapest round-trip price found within the last 5 days was $267 on Frontier (Aug 12-Aug 19).
How far ahead should I book a flight from San Antonio to Chicago?
To ensure you get the cheapest price possible for a flight from San Antonio to Chicago, you should look to book at least 69 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
The best insider tips for San Antonio to Chicago 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 trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated July 23, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from San Antonio to Chicago. 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.
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from San Antonio to Chicago. 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?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 23, 2026.
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San Antonio and Chicago flights
Browse other San Antonio and Chicago flight options. Last updated on July 23, 2026.
Other flights from San Antonio
Browse through other flights departing from San Antonio. Flights are based on user searches made on Cheapflights and were last updated on July 23, 2026.
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Check out other popular destinations found by fellow travelers in 2026
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Consider these flights traveling from San Antonio to Chicago.
Top 4 airlines flying from San Antonio to Chicago
Discover the top 4 airlines that operate flights from San Antonio to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$221 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$391 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$256 | Average$429 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$287 | Average$441 | FlexibilityNo cancel fee | On-time69% |