$78+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAT
Apr 4 — Apr 111
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 50 days in advance, depart on a Tuesday or Wednesday and return on a Thursday
Cheap flight deals from Chicago to San Antonio
Cheapest
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 March 5, 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 March 5, 2026.
This CheapOair deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/712:44 pm
ORD
- SAT
1 stop11h 15m
Multiple Airlines
Wed 3/186:45 am
SAT
- ORD
1 stop26h 58m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/236:10 pm
ORD
- SAT
1 stop15h 17m
Spirit Airlines
Wed 3/2510:22 am
SAT
- ORD
1 stop9h 29m
Spirit Airlines
Deal found 3/1![Spirit Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:08 pm
ORD
- SAT
2 stops19h 09m
Multiple Airlines
Wed 4/292:12 pm
SAT
- ORD
1 stop18h 53m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:01 am
MDW
- SAT
1 stop7h 26m
Multiple Airlines
Tue 4/1410:22 am
SAT
- MDW
2 stops11h 52m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/46:10 pm
ORD
- SAT
1 stop15h 17m
Multiple Airlines
Tue 4/77:45 am
SAT
- ORD
2 stops15h 55m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$281
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/410:40 pm
MDW
- SAT
Nonstop2h 55m
Southwest
Tue 4/72:35 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 3/1![Southwest logo]()
$281
This Mytrip deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:25 am
ORD
- SAT
2 stops22h 02m
Spirit Airlines
Mon 4/1310:22 am
SAT
- ORD
2 stops22h 28m
Spirit Airlines
Deal found 3/4![Spirit Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/166:00 am
MDW
- SAT
2 stops17h 51m
Multiple Airlines
Sun 4/192:12 pm
SAT
- MDW
1 stop17h 52m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/251:27 pm
ORD
- SAT
1 stop10h 24m
Multiple Airlines
Sun 4/266:00 am
SAT
- ORD
2 stops17h 01m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 3/3111:05 am
MDW
- SAT
Nonstop3h 00m
Southwest
Tue 4/75:40 pm
SAT
- MDW
1 stop4h 05m
Southwest
Deal found 3/2![Southwest logo]()
$283
This Booking.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/184:18 pm
ORD
- SAT
1 stop21h 05m
Frontier
Thu 3/264:54 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 2/28![Frontier logo]()
$284
This CheapOair deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/24:36 pm
ORD
- SAT
1 stop16h 51m
Spirit Airlines
Thu 4/910:22 am
SAT
- ORD
1 stop12h 55m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$285
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 March 5, 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 March 5, 2026.
This United Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/258:03 pm
ORD
- SAT
Nonstop3h 12m
United Airlines
Sat 3/285:00 am
SAT
- ORD
1 stop5h 07m
United Airlines
Deal found 3/1![United Airlines logo]()
$306
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 5/259:40 pm
MDW
- SAT
Nonstop2h 50m
Southwest
Sat 5/303:40 pm
SAT
- MDW
1 stop7h 05m
Southwest
Deal found 3/1![Southwest logo]()
$325
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:10 am
ORD
- SAT
1 stop5h 49m
Delta
Mon 4/205:10 am
SAT
- ORD
1 stop7h 35m
Delta
Deal found 2/28![Delta logo]()
$332
This United Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/157:30 am
ORD
- SAT
1 stop5h 38m
United Airlines
Sat 4/186:49 am
SAT
- ORD
Nonstop2h 55m
United Airlines
Deal found 3/3![United Airlines logo]()
$307
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/210:45 am
MDW
- SAT
1 stop6h 36m
Delta
Tue 4/75:10 am
SAT
- MDW
1 stop7h 19m
Delta
Deal found 2/28![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/248:35 pm
MDW
- SAT
Nonstop2h 55m
Southwest
Thu 3/265:35 am
SAT
- MDW
1 stop5h 00m
Southwest
Deal found 2/28![Southwest logo]()
$343
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/712:47 pm
MDW
- SAT
1 stop5h 27m
Delta
Mon 4/134:30 pm
SAT
- MDW
1 stop5h 58m
Delta
Deal found 2/28![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/269:55 pm
MDW
- SAT
Nonstop2h 55m
Southwest
Tue 3/3111:10 am
SAT
- MDW
2 stops5h 50m
Southwest
Deal found 3/4![Southwest logo]()
$348
This United Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/288:03 pm
ORD
- SAT
Nonstop3h 12m
United Airlines
Sat 4/46:49 am
SAT
- ORD
Nonstop2h 55m
United Airlines
Deal found 2/28![United Airlines logo]()
$368
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/254:00 pm
MDW
- SAT
1 stop7h 00m
Southwest
Sat 3/286:15 am
SAT
- MDW
1 stop5h 20m
Southwest
Deal found 3/1![Southwest logo]()
$357
This United Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 3/268:03 pm
ORD
- SAT
Nonstop3h 12m
United Airlines
Tue 3/315:30 pm
SAT
- ORD
Nonstop2h 56m
United Airlines
Deal found 3/4![United Airlines logo]()
$376
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 5/253:05 pm
ORD
- SAT
1 stop6h 50m
Southwest
Sat 5/306:35 am
SAT
- ORD
1 stop8h 55m
Southwest
Deal found 3/1![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:05 pm
ORD
- SAT
1 stop6h 39m
Delta
Sun 5/315:20 am
SAT
- ORD
1 stop5h 07m
Delta
Deal found 2/28![Delta logo]()
$407
This United Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/288:03 pm
ORD
- SAT
Nonstop3h 12m
United Airlines
Thu 4/27:15 pm
SAT
- ORD
1 stop6h 11m
United Airlines
Deal found 3/1![United Airlines logo]()
$378
This Southwest deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/242:00 pm
ORD
- SAT
2 stops8h 00m
Southwest
Tue 4/284:55 pm
SAT
- ORD
1 stop7h 00m
Southwest
Deal found 3/4![Southwest logo]()
$367
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 3/238:03 pm
ORD
- SAT
Nonstop3h 12m
United Airlines
Mon 3/306:49 am
SAT
- ORD
Nonstop2h 55m
United Airlines
Deal found 3/2![United Airlines logo]()
$389
This Southwest deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/205:30 am
MDW
- SAT
2 stops5h 55m
Southwest
Thu 4/235:45 am
SAT
- MDW
1 stop6h 05m
Southwest
Deal found 3/3![Southwest logo]()
$372
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 5/147:45 pm
ORD
- SAT
Nonstop3h 09m
United Airlines
Sun 5/176:02 pm
SAT
- ORD
1 stop5h 13m
United Airlines
Deal found 3/2![United Airlines logo]()
$397
This Southwest deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/2910:05 am
MDW
- SAT
Nonstop2h 50m
Southwest
Sun 5/33:05 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 3/3![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/2911:55 am
ORD
- SAT
2 stops9h 50m
Southwest
Sun 5/35:25 am
SAT
- ORD
2 stops7h 50m
Southwest
Deal found 3/3![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 5/149:40 pm
MDW
- SAT
Nonstop2h 50m
Southwest
Sun 5/175:20 pm
SAT
- MDW
1 stop7h 00m
Southwest
Deal found 3/2![Southwest logo]()
$397
This Southwest deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 3/275:05 am
MDW
- SAT
1 stop5h 35m
Southwest
Wed 4/17:05 am
SAT
- MDW
2 stops7h 30m
Southwest
Deal found 3/4![Southwest logo]()
$398
This Southwest deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 3/275:05 am
MDW
- SAT
1 stop7h 10m
Southwest
Mon 3/303:25 pm
SAT
- MDW
Nonstop2h 30m
Southwest
Deal found 3/4![Southwest logo]()
$404
Last-minute flights from Chicago to San AntonioDiscover last-minute flight deals from Chicago to San Antonio. Data last updated March 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San Antonio. Data last updated March 5, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/712:44 pm
ORD
- SAT
1 stop11h 15m
Multiple Airlines
Wed 3/186:45 am
SAT
- ORD
1 stop26h 58m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$278
This Booking.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/184:18 pm
ORD
- SAT
1 stop21h 05m
Frontier
Thu 3/264:54 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 2/28![Frontier logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/236:10 pm
ORD
- SAT
1 stop15h 17m
Spirit Airlines
Wed 3/2510:22 am
SAT
- ORD
1 stop9h 29m
Spirit Airlines
Deal found 3/1![Spirit Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 3/3111:05 am
MDW
- SAT
Nonstop3h 00m
Southwest
Tue 4/75:40 pm
SAT
- MDW
1 stop4h 05m
Southwest
Deal found 3/2![Southwest logo]()
$283
This CheapOair deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/24:36 pm
ORD
- SAT
1 stop16h 51m
Spirit Airlines
Thu 4/910:22 am
SAT
- ORD
1 stop12h 55m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/46:10 pm
ORD
- SAT
1 stop15h 17m
Multiple Airlines
Tue 4/77:45 am
SAT
- ORD
2 stops15h 55m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$281
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/410:40 pm
MDW
- SAT
Nonstop2h 55m
Southwest
Tue 4/72:35 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 3/1![Southwest logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:01 am
MDW
- SAT
1 stop7h 26m
Multiple Airlines
Tue 4/1410:22 am
SAT
- MDW
2 stops11h 52m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$280
This Mytrip deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:25 am
ORD
- SAT
2 stops22h 02m
Spirit Airlines
Mon 4/1310:22 am
SAT
- ORD
2 stops22h 28m
Spirit Airlines
Deal found 3/4![Spirit Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/166:00 am
MDW
- SAT
2 stops17h 51m
Multiple Airlines
Sun 4/192:12 pm
SAT
- MDW
1 stop17h 52m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/221:27 pm
ORD
- SAT
1 stop10h 24m
Multiple Airlines
Sun 4/262:12 pm
SAT
- ORD
2 stops20h 11m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/251:27 pm
ORD
- SAT
1 stop10h 24m
Multiple Airlines
Sun 4/266:00 am
SAT
- ORD
2 stops17h 01m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$283
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 March 5, 2026.
Search for one-way flight options from Chicago to San Antonio. Find affordable one-way fares based on user searches. Data last updated March 5, 2026.
This Trip.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/83:29 pm
ORD
- SAT
1 stop8h 50m
Frontier
Deal found 3/3![Frontier logo]()
$78
This Trip.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/102:29 pm
ORD
- SAT
1 stop9h 50m
Frontier
Deal found 3/3![Frontier logo]()
$89
This Frontier deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/13:29 pm
ORD
- SAT
1 stop8h 50m
Frontier
Deal found 3/3![Frontier logo]()
$90
This Priceline deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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.
Sat 5/169:14 am
MDW
- SAT
1 stop8h 45m
Frontier
Deal found 3/3![Frontier logo]()
$90
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 4/282:15 pm
MDW
- SAT
2 stops25h 38m
Frontier
Deal found 3/5![Frontier logo]()
$94
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.
Thu 5/710:55 am
ORD
- SAT
1 stop27h 24m
Frontier
Deal found 3/5![Frontier logo]()
$96
This Booking.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/169:14 am
MDW
- SAT
1 stop24h 10m
Frontier
Deal found 3/3![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2811:07 am
ORD
- SAT
2 stops28h 46m
Frontier
Deal found 2/28![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/142:15 pm
MDW
- SAT
2 stops25h 38m
Frontier
Deal found 3/3![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/204:28 pm
ORD
- SAT
2 stops47h 25m
Frontier
Deal found 3/3![Frontier logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/272:15 pm
MDW
- SAT
2 stops49h 38m
Frontier
Deal found 3/3![Frontier logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/310:50 am
ORD
- SAT
1 stop27h 25m
Frontier
Deal found 3/2![Frontier logo]()
$102
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 March 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $279 (Kiwi.com) |
One-way from | $78 (Trip.com) |
Popular in | February |
Cheapest in | October |
Average price | $396 |
Good round-trip deal | $352 or less |
Good one-way deal | $166 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 March 5, 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
ORD - SAT
ORDSAT
Chicago O'Hare Intl
Wed 3/25
8:03 pm-11:15 pm
Nonstop3h 12m
San Antonio
Sat 3/28
5:00 am-10:07 am
1 stop5h 07m
$306
ChicagoSan Antonio
ORD - SAT
ORDSAT
Chicago O'Hare Intl
Wed 4/15
7:30 am-1:08 pm
1 stop5h 38m
San Antonio
Sat 4/18
6:49 am-9:44 am
Nonstop2h 55m
$307
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Mon 5/25
9:40 pm-12:30 am
Nonstop2h 50m
San Antonio
Sat 5/30
3:40 pm-10:45 pm
1 stop7h 05m
$325
ChicagoSan Antonio
ORD - SAT
ORDSAT
Chicago O'Hare Intl
Tue 4/14
7:10 am-12:59 pm
1 stop5h 49m
San Antonio
Mon 4/20
5:10 am-12:45 pm
1 stop7h 35m
$332
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Thu 4/2
10:45 am-5:21 pm
1 stop6h 36m
San Antonio
Tue 4/7
5:10 am-12:29 pm
1 stop7h 19m
$332
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Tue 4/7
12:47 pm-6:14 pm
1 stop5h 27m
San Antonio
Mon 4/13
4:30 pm-10:28 pm
1 stop5h 58m
$332
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Tue 3/24
8:35 pm-11:30 pm
Nonstop2h 55m
San Antonio
Thu 3/26
5:35 am-10:35 am
1 stop5h 00m
$343
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Thu 3/26
9:55 pm-12:50 am
Nonstop2h 55m
San Antonio
Tue 3/31
11:10 am-5:00 pm
2 stops5h 50m
$348
ChicagoSan Antonio
MDW - SAT
MDWSAT
Chicago Midway
Wed 3/25
4:00 pm-11:00 pm
1 stop7h 00m
San Antonio
Sat 3/28
6:15 am-11:35 am
1 stop5h 20m
$357
ChicagoSan Antonio
ORD - SAT
ORDSAT
Chicago O'Hare Intl
Mon 5/25
3:05 pm-9:55 pm
1 stop6h 50m
San Antonio
Sat 5/30
6:35 am-3:30 pm
1 stop8h 55m
$361
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 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 Accuracy3 stars | 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
How far ahead should I book a flight from Chicago to San Antonio?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to San Antonio. Price data was last updated on February 27, 2026.
Booking 50 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 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 $59). Flying from Chicago to San Antonio in September is currently the most expensive (average of $154). 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 March 5, 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 at noon, which is usually more expensive.
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 February 21, 2026.
Travelers seeking maximum savings on their Chicago to San Antonio flight should consider departing on Saturday afternoons when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
How much does it cost to fly round-trip from Chicago to San Antonio?
What’s the top layover airport for flights from Chicago to San Antonio?
Share of 1-stop round-trip flights from Chicago to San Antonio 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 Chicago to San Antonio on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to San Antonio?
Average round-trip fare for 1-stop flights from Chicago to San Antonio, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Los Angeles (LAX) is the most affordable 1-stop option, with an average round-trip price of $236.
What’s the fastest layover option from Chicago to San Antonio?
Shortest average travel time for 1-stop one-way flights from Chicago to San Antonio, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Orlando (MCO) have the shortest average one-way travel time for 1-stop routes: 9h 22m.
Which airport typically offers the quickest layover for flights from Chicago to San Antonio?
Average layover duration for 1-stop one-way flights from Chicago to San Antonio, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Orlando (MCO) offer the fastest connection on this route, with an average layover time of 2h 47m.
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 March 5, 2026.
Read reviews from past customers who have flown Southwest, United Airlines, and American 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.
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
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
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Top 5 airlines flying from Chicago to San Antonio
Discover the top 5 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 March 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$101 | Average$200 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$167 | Average$253 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$197 | Average$377 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$214 | Average$420 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$402 | FlexibilityNo cancel fee | On-time63% |