$90+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — CHI
Apr 9 — Apr 161
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 70 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 March 10, 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 March 10, 2026.
This Booking.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
Sat 4/184:04 pm
SAT
- ORD
1 stop17h 41m
Frontier
Mon 4/2010:55 am
ORD
- SAT
1 stop28h 14m
Frontier
Deal found 3/10![Frontier logo]()
$201
This Booking.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
Mon 3/3010:05 am
SAT
- ORD
1 stop14h 52m
Frontier
Wed 4/13:29 pm
ORD
- SAT
1 stop8h 50m
Frontier
Deal found 3/9![Frontier logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/154:49 pm
SAT
- ORD
1 stop17h 01m
Multiple Airlines
Wed 4/221:27 pm
ORD
- SAT
1 stop10h 24m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 5/93:34 pm
SAT
- ORD
1 stop18h 16m
Multiple Airlines
Tue 5/124:28 pm
ORD
- SAT
2 stops20h 49m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$214
This Expedia deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/810:22 am
SAT
- ORD
1 stop9h 29m
Multiple Airlines
Mon 4/132:29 pm
ORD
- SAT
1 stop24h 40m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 pm
SAT
- ORD
1 stop23h 00m
Frontier
Mon 4/2010:55 am
ORD
- SAT
1 stop28h 14m
Frontier
Deal found 3/9![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1410:22 am
SAT
- ORD
1 stop9h 29m
Multiple Airlines
Mon 4/208:58 pm
ORD
- SAT
2 stops18h 11m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$220
This Expedia deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/1710:23 am
SAT
- ORD
1 stop29h 00m
Frontier
Mon 4/2010:55 am
ORD
- SAT
1 stop28h 14m
Frontier
Deal found 3/10![Frontier logo]()
$221
This Expedia deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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.
Mon 5/46:31 pm
SAT
- ORD
1 stop12h 16m
Frontier
Wed 5/69:18 pm
ORD
- SAT
1 stop14h 22m
Frontier
Deal found 3/6![Frontier logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/154:49 pm
SAT
- ORD
1 stop17h 01m
Frontier
Sat 4/185:50 am
ORD
- SAT
2 stops11h 45m
Frontier
Deal found 3/6![Frontier logo]()
$228
This Booking.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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.
Tue 3/172:08 pm
SAT
- MDW
1 stop28h 05m
Frontier
Mon 3/239:51 pm
MDW
- SAT
1 stop15h 32m
Frontier
Deal found 3/5![Frontier logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/186:30 pm
SAT
- MDW
1 stop13h 29m
Frontier
Mon 4/202:15 pm
MDW
- SAT
2 stops49h 38m
Frontier
Deal found 3/6![Frontier logo]()
$261
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 March 10, 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 March 10, 2026.
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 3/305:30 pm
SAT
- ORD
Nonstop2h 56m
United Airlines
Sat 4/42:00 pm
ORD
- SAT
1 stop6h 42m
United Airlines
Deal found 3/8![United Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 3/305:25 pm
SAT
- MDW
1 stop6h 40m
Southwest
Sat 4/410:05 am
MDW
- SAT
2 stops6h 15m
Southwest
Deal found 3/8![Southwest logo]()
$302
This Delta deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/710:52 am
SAT
- MDW
1 stop5h 20m
Delta
Tue 5/1212:51 pm
MDW
- SAT
1 stop5h 32m
Delta
Deal found 3/6![Delta logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 6/47:26 pm
SAT
- RFD
2 stops24h 54m
Multiple Airlines
Sun 6/711:27 am
RFD
- SAT
1 stop12h 24m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$370
This Southwest deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/145:40 pm
SAT
- MDW
1 stop4h 05m
Southwest
Sat 4/186:15 pm
MDW
- SAT
Nonstop2h 50m
Southwest
Deal found 3/6![Southwest logo]()
$303
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 5/122:25 pm
SAT
- ORD
1 stop5h 47m
United Airlines
Thu 5/149:05 am
ORD
- SAT
Nonstop3h 10m
United Airlines
Deal found 3/8![United Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 5/66:20 am
SAT
- MDW
1 stop5h 47m
Delta
Mon 5/111:59 pm
MDW
- SAT
1 stop7h 33m
Delta
Deal found 3/8![Delta logo]()
$324
This United Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/45:49 pm
SAT
- ORD
Nonstop2h 56m
United Airlines
Thu 5/72:20 pm
ORD
- SAT
1 stop6h 29m
United Airlines
Deal found 3/6![United Airlines logo]()
$321
This Southwest deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/42:10 pm
SAT
- MDW
1 stop6h 40m
Southwest
Thu 5/710:10 am
MDW
- SAT
Nonstop2h 50m
Southwest
Deal found 3/6![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 5/192:35 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Thu 5/219:40 pm
MDW
- SAT
Nonstop2h 50m
Southwest
Deal found 3/5![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 5/125:20 am
SAT
- MDW
1 stop7h 22m
Delta
Thu 5/1410:55 am
MDW
- SAT
1 stop6h 21m
Delta
Deal found 3/9![Delta logo]()
$362
This Southwest deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/72:40 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Tue 5/129:00 pm
MDW
- SAT
Nonstop2h 50m
Southwest
Deal found 3/6![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 6/181:40 pm
SAT
- ORD
Nonstop3h 01m
United Airlines
Tue 6/236:00 am
ORD
- SAT
1 stop6h 43m
United Airlines
Deal found 3/6![United Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 7/152:51 pm
SAT
- ORD
1 stop5h 27m
Delta
Mon 7/205:45 pm
ORD
- SAT
1 stop5h 27m
Delta
Deal found 3/5![Delta logo]()
$387
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/182:02 pm
SAT
- ORD
Nonstop2h 55m
United Airlines
Mon 4/2012:43 pm
ORD
- SAT
1 stop5h 00m
United Airlines
Deal found 3/8![United Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 6/166:30 am
SAT
- ORD
1 stop4h 59m
Delta
Sat 6/277:10 am
ORD
- SAT
1 stop5h 32m
Delta
Deal found 3/9![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/152:35 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Sun 4/199:40 pm
MDW
- SAT
Nonstop2h 50m
Southwest
Deal found 3/6![Southwest logo]()
$362
This United Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/152:02 pm
SAT
- ORD
Nonstop2h 55m
United Airlines
Sun 4/195:48 am
ORD
- SAT
1 stop5h 02m
United Airlines
Deal found 3/6![United Airlines logo]()
$372
This United Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 6/45:30 am
SAT
- ORD
1 stop4h 50m
United Airlines
Sun 6/79:10 am
ORD
- SAT
Nonstop3h 02m
United Airlines
Deal found 3/6![United Airlines logo]()
$379
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 7/410:40 am
SAT
- ORD
2 stops10h 20m
Southwest
Tue 8/47:10 am
ORD
- SAT
1 stop7h 40m
Southwest
Deal found 3/7![Southwest logo]()
$392
This United Airlines deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/22:02 pm
SAT
- ORD
Nonstop2h 55m
United Airlines
Thu 4/95:48 am
ORD
- SAT
1 stop7h 20m
United Airlines
Deal found 3/5![United Airlines logo]()
$388
Last-minute flights from San Antonio to ChicagoDiscover last-minute flight deals from San Antonio to Chicago. Data last updated March 10, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Chicago. Data last updated March 10, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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.
Tue 3/172:08 pm
SAT
- MDW
1 stop28h 05m
Frontier
Mon 3/239:51 pm
MDW
- SAT
1 stop15h 32m
Frontier
Deal found 3/5![Frontier logo]()
$259
This Priceline deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/242:13 pm
SAT
- ORD
1 stop9h 25m
Frontier
Thu 4/27:55 am
ORD
- SAT
1 stop7h 56m
Frontier
Deal found 3/6![Frontier logo]()
$235
This Booking.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
Mon 3/3010:05 am
SAT
- ORD
1 stop14h 52m
Frontier
Wed 4/13:29 pm
ORD
- SAT
1 stop8h 50m
Frontier
Deal found 3/9![Frontier logo]()
$206
This Expedia deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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.
Mon 3/3010:05 am
SAT
- ORD
1 stop14h 52m
Frontier
Sat 4/48:00 am
ORD
- SAT
1 stop26h 43m
Frontier
Deal found 3/8![Frontier logo]()
$234
This Expedia deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/810:22 am
SAT
- ORD
1 stop9h 29m
Multiple Airlines
Mon 4/132:29 pm
ORD
- SAT
1 stop24h 40m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 pm
SAT
- ORD
1 stop23h 00m
Frontier
Mon 4/2010:55 am
ORD
- SAT
1 stop28h 14m
Frontier
Deal found 3/9![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1410:22 am
SAT
- ORD
1 stop9h 29m
Multiple Airlines
Mon 4/208:58 pm
ORD
- SAT
2 stops18h 11m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/154:49 pm
SAT
- ORD
1 stop17h 01m
Multiple Airlines
Wed 4/221:27 pm
ORD
- SAT
1 stop10h 24m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/154:49 pm
SAT
- ORD
1 stop17h 01m
Frontier
Sat 4/185:50 am
ORD
- SAT
2 stops11h 45m
Frontier
Deal found 3/6![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/163:00 pm
SAT
- ORD
1 stop18h 50m
Frontier
Mon 4/208:58 pm
ORD
- SAT
2 stops42h 55m
Frontier
Deal found 3/10![Frontier logo]()
$229
This Expedia deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/1710:23 am
SAT
- ORD
1 stop29h 00m
Frontier
Mon 4/2010:55 am
ORD
- SAT
1 stop28h 14m
Frontier
Deal found 3/10![Frontier logo]()
$221
This Booking.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
Sat 4/184:04 pm
SAT
- ORD
1 stop17h 41m
Frontier
Mon 4/2010:55 am
ORD
- SAT
1 stop28h 14m
Frontier
Deal found 3/10![Frontier logo]()
$201
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 March 10, 2026.
Search for one-way flight options from San Antonio to Chicago. Find affordable one-way fares based on user searches. Data last updated March 10, 2026.
This Booking.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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.
Fri 5/18:25 pm
SAT
- ORD
1 stop9h 43m
Frontier
Deal found 3/6![Frontier logo]()
$90
This Expedia deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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.
Sat 4/184:04 pm
SAT
- ORD
1 stop17h 41m
Frontier
Deal found 3/5![Frontier logo]()
$96
This Expedia deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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.
Sat 4/186:30 pm
SAT
- MDW
1 stop13h 29m
Frontier
Deal found 3/5![Frontier logo]()
$96
This Booking.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
Wed 3/256:45 am
SAT
- ORD
1 stop26h 58m
Frontier
Deal found 3/9![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 5/93:34 pm
SAT
- ORD
1 stop18h 16m
Frontier
Deal found 3/9![Frontier logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/1410:22 am
SAT
- ORD
1 stop9h 29m
Spirit Airlines
Deal found 3/6![Spirit Airlines logo]()
$100
This Cheapflightsfares deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 3/241:22 pm
SAT
- ORD
1 stop6h 41m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/154:49 pm
SAT
- MDW
2 stops22h 15m
Frontier
Deal found 3/9![Frontier logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/214:04 pm
SAT
- MDW
2 stops27h 27m
Frontier
Deal found 3/10![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/53:14 pm
SAT
- ORD
2 stops19h 30m
Frontier
Deal found 3/6![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/144:04 pm
SAT
- MDW
2 stops27h 27m
Frontier
Deal found 3/6![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/83:14 pm
SAT
- ORD
2 stops31h 25m
Frontier
Deal found 3/6![Frontier logo]()
$107
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 March 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $201 (Booking.com) |
One-way from | $90 (Booking.com) |
Popular in | December |
Cheapest in | September |
Average price | $393 |
Good round-trip deal | $387 or less |
Good one-way deal | $203 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 March 10, 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
Mon 3/30
5:30 pm-8:26 pm
Nonstop2h 56m
Chicago O'Hare Intl
Sat 4/4
2:00 pm-8:42 pm
1 stop6h 42m
$287
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Mon 3/30
5:25 pm-12:05 am
1 stop6h 40m
Chicago Midway
Sat 4/4
10:05 am-4:20 pm
2 stops6h 15m
$302
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Tue 4/14
5:40 pm-9:45 pm
1 stop4h 05m
Chicago Midway
Sat 4/18
6:15 pm-9:05 pm
Nonstop2h 50m
$303
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Tue 5/12
2:25 pm-8:12 pm
1 stop5h 47m
Chicago O'Hare Intl
Thu 5/14
9:05 am-12:15 pm
Nonstop3h 10m
$314
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Mon 5/4
5:49 pm-8:45 pm
Nonstop2h 56m
Chicago O'Hare Intl
Thu 5/7
2:20 pm-8:49 pm
1 stop6h 29m
$321
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Mon 5/4
2:10 pm-8:50 pm
1 stop6h 40m
Chicago Midway
Thu 5/7
10:10 am-1:00 pm
Nonstop2h 50m
$321
Quickest round-trip
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Tue 5/19
2:35 pm-5:10 pm
Nonstop2h 35m
Chicago Midway
Thu 5/21
9:40 pm-12:30 am
Nonstop2h 50m
$322
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Thu 5/7
2:40 pm-5:15 pm
Nonstop2h 35m
Chicago Midway
Tue 5/12
9:00 pm-11:50 pm
Nonstop2h 50m
$322
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Thu 5/7
10:52 am-4:12 pm
1 stop5h 20m
Chicago Midway
Tue 5/12
12:51 pm-6:23 pm
1 stop5h 32m
$324
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Wed 5/6
6:20 am-12:07 pm
1 stop5h 47m
Chicago Midway
Mon 5/11
1:59 pm-9:32 pm
1 stop7h 33m
$324
Showing 1-10 of 51 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 March.
| 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 Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | 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
How far ahead should I book a flight from San Antonio to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from San Antonio to Chicago. Price data was last updated on March 6, 2026.
To ensure you get the cheapest price possible for a flight from San Antonio to Chicago, you should look to book at least 70 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.
What is the cheapest month to book a flight from San Antonio to Chicago?
Currently, January is the cheapest month in which you can book a flight from San Antonio to Chicago (average of $54). Flying from San Antonio to Chicago in May is currently the most expensive (average of $156). 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 March 10, 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 morning, which can drop the price by up to 40% versus a flight in the evening.
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 March 10, 2026.
The most flights from SAT to CHI are scheduled on a Monday (28 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).
What’s the top layover airport for flights from San Antonio to Chicago?
Share of 1-stop round-trip flights from San Antonio to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.
Orlando (MCO) – chosen by Cheapflights users on 75% of 1-stop itineraries from San Antonio to Chicago on Cheapflights.
What’s the cheapest layover airport for flights from San Antonio to Chicago?
Average round-trip fare for 1-stop flights from San Antonio to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of $173.
What’s the fastest layover option from San Antonio to Chicago?
Shortest average travel time for 1-stop one-way flights from San Antonio to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 12h 06m.
Which airport typically offers the quickest layover for flights from San Antonio to Chicago?
Average layover duration for 1-stop one-way flights from San Antonio to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Atlanta (ATL) offer the fastest connection on this route, with an average layover time of 7h 05m.
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 March 10, 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.
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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San Antonio and Chicago flights
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Top 5 airlines flying from San Antonio to Chicago
Discover the top 5 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 March 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$213 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$143 | Average$274 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$215 | Average$370 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$256 | Average$396 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$260 | Average$435 | FlexibilityNo cancel fee | On-time69% |