$141+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — CHI
Jun 4 — Jun 111
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 May 5, 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 May 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 6/304:44 pm
SAT
- ORD
1 stop19h 40m
Multiple Airlines
Fri 7/109:57 pm
ORD
- SAT
1 stop20h 57m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$296
This United Airlines deal was found by Cheapflights users on 5/3. 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 5/276:40 am
SAT
- ORD
Nonstop2h 58m
United Airlines
Wed 6/107:59 pm
ORD
- SAT
Nonstop2h 59m
United Airlines
Deal found 5/3![United Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 5/3. 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.
Tue 6/169:20 am
SAT
- MDW
Nonstop2h 35m
Southwest
Tue 6/239:00 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/3![Southwest logo]()
$297
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:00 am
SAT
- ORD
Nonstop3h 02m
American Airlines
Tue 6/239:00 pm
ORD
- SAT
Nonstop2h 59m
American Airlines
Deal found 5/1![American Airlines logo]()
$298
This CheapOair deal was found by Cheapflights users on 5/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/228:59 pm
SAT
- ORD
1 stop8h 29m
Frontier
Mon 7/279:57 pm
ORD
- SAT
1 stop20h 57m
Frontier
Deal found 5/5![Frontier logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 5/197:54 pm
SAT
- ORD
2 stops12h 01m
Frontier
Wed 5/279:37 pm
ORD
- SAT
1 stop21h 22m
Frontier
Deal found 5/3![Frontier logo]()
$301
This Mytrip deal was found by Cheapflights users on 5/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:54 pm
SAT
- ORD
1 stop24h 38m
Multiple Airlines
Sun 5/315:05 am
ORD
- SAT
1 stop11h 11m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$302
This American Airlines deal was found by Cheapflights users on 5/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:27 pm
SAT
- ORD
Nonstop3h 17m
American Airlines
Wed 6/310:00 am
ORD
- SAT
Nonstop2h 52m
American Airlines
Deal found 5/4![American Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/262:35 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Mon 6/19:40 pm
MDW
- SAT
Nonstop2h 50m
Southwest
Deal found 4/30![Southwest logo]()
$303
This Frontier deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 7/38:56 pm
SAT
- ORD
1 stop8h 11m
Frontier
Tue 7/77:15 am
ORD
- SAT
1 stop12h 59m
Frontier
Deal found 4/30![Frontier logo]()
$304
This United Airlines deal was found by Cheapflights users on 5/5. 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.
Tue 6/21:20 pm
SAT
- ORD
Nonstop3h 01m
United Airlines
Tue 6/97:59 pm
ORD
- SAT
Nonstop2h 59m
United Airlines
Deal found 5/5![United Airlines logo]()
$305
This Southwest deal was found by Cheapflights users on 5/5. 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 6/232:00 pm
SAT
- MDW
Nonstop2h 40m
Southwest
Tue 6/239:00 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/5![Southwest logo]()
$305
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 May 5, 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 May 5, 2026.
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/285:20 am
SAT
- ORD
1 stop7h 41m
Delta
Wed 6/39:49 am
ORD
- SAT
1 stop8h 34m
Delta
Deal found 4/30![Delta logo]()
$323
This Southwest deal was found by Cheapflights users on 5/3. 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.
Tue 6/92:00 pm
SAT
- MDW
Nonstop2h 40m
Southwest
Sat 6/138:30 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/3![Southwest logo]()
$332
This United Airlines deal was found by Cheapflights users on 5/1. 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 10/146:40 am
SAT
- ORD
Nonstop2h 58m
United Airlines
Thu 10/159:17 am
ORD
- SAT
Nonstop2h 53m
United Airlines
Deal found 5/1![United Airlines logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Wed 5/278:59 pm
SAT
- RFD
1 stop15h 22m
Multiple Airlines
Sun 5/3111:27 am
RFD
- SAT
1 stop28h 49m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$472
This Delta deal was found by Cheapflights users on 5/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:25 am
SAT
- MDW
1 stop6h 31m
Delta
Mon 6/15:08 pm
MDW
- SAT
1 stop5h 23m
Delta
Deal found 5/4![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/265:40 pm
SAT
- MDW
1 stop4h 05m
Southwest
Fri 5/299:40 pm
MDW
- SAT
Nonstop2h 50m
Southwest
Deal found 4/30![Southwest logo]()
$338
This Southwest deal was found by Cheapflights users on 5/4. 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.
Tue 6/237:25 am
SAT
- MDW
1 stop5h 00m
Southwest
Mon 6/299:25 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/4![Southwest logo]()
$342
This United Airlines deal was found by Cheapflights users on 5/5. 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 6/187:20 pm
SAT
- ORD
1 stop5h 25m
United Airlines
Thu 6/257:58 pm
ORD
- SAT
Nonstop2h 59m
United Airlines
Deal found 5/5![United Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 5/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:11 pm
SAT
- ORD
1 stop5h 48m
Delta
Tue 6/96:35 am
ORD
- SAT
1 stop7h 00m
Delta
Deal found 5/4![Delta logo]()
$348
This United Airlines deal was found by Cheapflights users on 5/1. 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 5/277:20 pm
SAT
- ORD
1 stop5h 25m
United Airlines
Sun 5/318:00 pm
ORD
- SAT
Nonstop2h 59m
United Airlines
Deal found 5/1![United Airlines logo]()
$382
This Delta deal was found by Cheapflights users on 5/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2411:30 am
SAT
- ORD
1 stop6h 59m
Delta
Mon 6/296:30 am
ORD
- SAT
1 stop5h 16m
Delta
Deal found 5/1![Delta logo]()
$352
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/2911:10 am
SAT
- ORD
1 stop4h 20m
Southwest
Sat 5/302:05 pm
ORD
- SAT
1 stop6h 55m
Southwest
Deal found 4/30![Southwest logo]()
$353
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Tue 6/96:40 am
SAT
- ORD
Nonstop2h 58m
United Airlines
Wed 6/107:59 pm
ORD
- SAT
Nonstop2h 59m
United Airlines
Deal found 5/1![United Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 5/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:11 pm
SAT
- ORD
1 stop5h 48m
Delta
Mon 6/85:30 am
ORD
- SAT
1 stop8h 05m
Delta
Deal found 5/2![Delta logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Wed 7/88:59 pm
SAT
- RFD
1 stop15h 25m
Multiple Airlines
Sun 7/121:14 pm
RFD
- SAT
2 stops29h 40m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$472
This Southwest deal was found by Cheapflights users on 5/4. 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 5/2912:20 pm
SAT
- MDW
1 stop4h 45m
Southwest
Wed 6/310:10 am
MDW
- SAT
2 stops6h 05m
Southwest
Deal found 5/4![Southwest logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Sat 6/138:56 pm
SAT
- RFD
1 stop15h 27m
Multiple Airlines
Thu 6/1811:27 am
RFD
- SAT
2 stops23h 23m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$475
This Delta deal was found by Cheapflights users on 5/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/22:27 pm
SAT
- ORD
1 stop8h 00m
Delta
Fri 6/55:30 am
ORD
- SAT
1 stop8h 02m
Delta
Deal found 5/4![Delta logo]()
$372
This Southwest deal was found by Cheapflights users on 5/1. 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.
Sun 6/73:25 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Tue 6/910:25 am
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/1![Southwest logo]()
$372
This Southwest deal was found by Cheapflights users on 5/2. 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.
Sat 6/62:00 pm
SAT
- MDW
2 stops7h 10m
Southwest
Tue 6/95:50 pm
MDW
- SAT
1 stop4h 30m
Southwest
Deal found 5/2![Southwest logo]()
$373
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/237:55 am
SAT
- MDW
1 stop8h 17m
Delta
Mon 6/15:08 pm
MDW
- SAT
1 stop7h 36m
Delta
Deal found 4/30![Delta logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Wed 7/158:59 pm
SAT
- RFD
1 stop15h 25m
Multiple Airlines
Sun 7/199:19 am
RFD
- SAT
2 stops24h 30m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$559
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 7/297:40 am
SAT
- ORD
1 stop6h 34m
Delta
Mon 8/36:30 am
ORD
- SAT
1 stop6h 46m
Delta
Deal found 4/30![Delta logo]()
$387
This Delta deal was found by Cheapflights users on 5/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2210:38 am
SAT
- ORD
1 stop6h 34m
Delta
Mon 7/276:35 am
ORD
- SAT
1 stop6h 57m
Delta
Deal found 5/1![Delta logo]()
$387
This Delta deal was found by Cheapflights users on 5/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:30 am
SAT
- MDW
1 stop5h 21m
Delta
Tue 10/131:05 pm
MDW
- SAT
1 stop7h 17m
Delta
Deal found 5/1![Delta logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Wed 6/178:56 pm
SAT
- RFD
1 stop15h 27m
Multiple Airlines
Sun 6/219:19 am
RFD
- SAT
2 stops9h 37m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$838
Last-minute flights from San Antonio to ChicagoDiscover last-minute flight deals from San Antonio to Chicago. Data last updated May 5, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Chicago. Data last updated May 5, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 5/197:54 pm
SAT
- ORD
2 stops12h 01m
Frontier
Wed 5/279:37 pm
ORD
- SAT
1 stop21h 22m
Frontier
Deal found 5/3![Frontier logo]()
$301
This Booking.com deal was found by Cheapflights users on 5/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/217:54 pm
SAT
- ORD
1 stop24h 38m
Frontier
Sun 5/249:37 pm
ORD
- SAT
1 stop21h 22m
Frontier
Deal found 5/4![Frontier logo]()
$304
This Trip.com deal was found by Cheapflights users on 5/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/227:54 pm
SAT
- ORD
1 stop24h 38m
Frontier
Mon 5/259:37 pm
ORD
- SAT
1 stop21h 22m
Frontier
Deal found 5/5![Frontier logo]()
$307
This United Airlines deal was found by Cheapflights users on 5/3. 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 5/276:40 am
SAT
- ORD
Nonstop2h 58m
United Airlines
Wed 6/107:59 pm
ORD
- SAT
Nonstop2h 59m
United Airlines
Deal found 5/3![United Airlines logo]()
$297
This Mytrip deal was found by Cheapflights users on 5/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:54 pm
SAT
- ORD
1 stop24h 38m
Multiple Airlines
Sun 5/315:05 am
ORD
- SAT
1 stop11h 11m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$302
This American Airlines deal was found by Cheapflights users on 5/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:27 pm
SAT
- ORD
Nonstop3h 17m
American Airlines
Wed 6/310:00 am
ORD
- SAT
Nonstop2h 52m
American Airlines
Deal found 5/4![American Airlines logo]()
$303
This United Airlines deal was found by Cheapflights users on 5/5. 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.
Tue 6/21:20 pm
SAT
- ORD
Nonstop3h 01m
United Airlines
Tue 6/97:59 pm
ORD
- SAT
Nonstop2h 59m
United Airlines
Deal found 5/5![United Airlines logo]()
$305
This Southwest deal was found by Cheapflights users on 5/4. 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.
Wed 6/311:20 am
SAT
- MDW
1 stop4h 20m
Southwest
Wed 6/109:00 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/4![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 5/3. 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.
Tue 6/169:20 am
SAT
- MDW
Nonstop2h 35m
Southwest
Tue 6/239:00 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/3![Southwest logo]()
$297
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:00 am
SAT
- ORD
Nonstop3h 02m
American Airlines
Tue 6/239:00 pm
ORD
- SAT
Nonstop2h 59m
American Airlines
Deal found 5/1![American Airlines logo]()
$298
This Southwest deal was found by Cheapflights users on 5/5. 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 6/232:00 pm
SAT
- MDW
Nonstop2h 40m
Southwest
Tue 6/239:00 pm
MDW
- SAT
Nonstop2h 40m
Southwest
Deal found 5/5![Southwest logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 6/304:44 pm
SAT
- ORD
1 stop19h 40m
Multiple Airlines
Fri 7/109:57 pm
ORD
- SAT
1 stop20h 57m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$296
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 May 5, 2026.
Search for one-way flight options from San Antonio to Chicago. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
This Super.com deal was found by Cheapflights users on 5/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/257:54 pm
SAT
- ORD
1 stop24h 38m
Frontier
Deal found 5/5![Frontier logo]()
$141
This Frontier deal was found by Cheapflights users on 5/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/278:56 pm
SAT
- ORD
1 stop8h 11m
Frontier
Deal found 5/4![Frontier logo]()
$145
This Trip.com deal was found by Cheapflights users on 5/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/187:54 pm
SAT
- ORD
1 stop24h 38m
Frontier
Deal found 5/4![Frontier logo]()
$146
This Super.com deal was found by Cheapflights users on 5/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:54 pm
SAT
- ORD
1 stop24h 38m
Frontier
Deal found 5/3![Frontier logo]()
$148
This United Airlines deal was found by Cheapflights users on 5/4. 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.
Tue 5/266:40 am
SAT
- ORD
Nonstop2h 58m
United Airlines
Deal found 5/4![United Airlines logo]()
$149
This Southwest deal was found by Cheapflights users on 5/2. 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 5/269:05 am
SAT
- MDW
Nonstop2h 35m
Southwest
Deal found 5/2![Southwest logo]()
$149
This Mytrip deal was found by Cheapflights users on 5/4. 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.
Tue 5/267:54 pm
SAT
- ORD
1 stop24h 38m
Frontier
Deal found 5/4![Frontier logo]()
$151
This Booking.com deal was found by Cheapflights users on 5/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:54 pm
SAT
- ORD
1 stop24h 38m
Frontier
Deal found 5/1![Frontier logo]()
$152
This American Airlines deal was found by Cheapflights users on 5/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:27 pm
SAT
- ORD
Nonstop3h 17m
American Airlines
Deal found 5/5![American Airlines logo]()
$153
This Southwest deal was found by Cheapflights users on 5/5. 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 7/282:00 pm
SAT
- MDW
Nonstop2h 40m
Southwest
Deal found 5/5![Southwest logo]()
$153
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/275:40 pm
SAT
- MDW
1 stop4h 05m
Southwest
Deal found 4/30![Southwest logo]()
$154
This United Airlines deal was found by Cheapflights users on 5/4. 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.
Mon 5/256:44 am
SAT
- ORD
Nonstop2h 58m
United Airlines
Deal found 5/4![United Airlines logo]()
$155
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 May 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $296 (Kiwi.com) |
One-way from | $141 (Super.com) |
Popular in | December |
Cheapest in | September |
Average price | $378 |
Good round-trip deal | $367 or less |
Good one-way deal | $221 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 May 5, 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 5/28
5:20 am-1:01 pm
1 stop7h 41m
Chicago O'Hare Intl
Wed 6/3
9:49 am-6:23 pm
1 stop8h 34m
$323
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Thu 5/28
5:25 am-11:56 am
1 stop6h 31m
Chicago Midway
Mon 6/1
5:08 pm-10:31 pm
1 stop5h 23m
$329
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Tue 6/9
2:00 pm-4:40 pm
Nonstop2h 40m
Chicago Midway
Sat 6/13
8:30 pm-11:10 pm
Nonstop2h 40m
$332
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Tue 5/26
5:40 pm-9:45 pm
1 stop4h 05m
Chicago Midway
Fri 5/29
9:40 pm-12:30 am
Nonstop2h 50m
$338
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Tue 6/23
7:25 am-12:25 pm
1 stop5h 00m
Chicago Midway
Mon 6/29
9:25 pm-12:05 am
Nonstop2h 40m
$342
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Thu 6/4
6:11 pm-11:59 pm
1 stop5h 48m
Chicago O'Hare Intl
Tue 6/9
6:35 am-1:35 pm
1 stop7h 00m
$348
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Wed 6/24
11:30 am-6:29 pm
1 stop6h 59m
Chicago O'Hare Intl
Mon 6/29
6:30 am-11:46 am
1 stop5h 16m
$352
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Fri 5/29
11:10 am-3:30 pm
1 stop4h 20m
Chicago O'Hare Intl
Sat 5/30
2:05 pm-9:00 pm
1 stop6h 55m
$353
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Thu 6/4
6:11 pm-11:59 pm
1 stop5h 48m
Chicago O'Hare Intl
Mon 6/8
5:30 am-1:35 pm
1 stop8h 05m
$354
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Fri 5/29
12:20 pm-5:05 pm
1 stop4h 45m
Chicago Midway
Wed 6/3
10:10 am-4:15 pm
2 stops6h 05m
$357
Showing 1-10 of 56 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 May.
| 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*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
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 21 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, August is the cheapest month in which you can book a flight from San Antonio to Chicago (average of $96). Flying from San Antonio to Chicago in June is currently the most expensive (average of $218). 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 May 5, 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 May 5, 2026.
The most flights from SAT to CHI are scheduled on a Monday (32 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).
How much does it cost to fly round-trip from San Antonio to Chicago?
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 May 5, 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.
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
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 locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 5, 2026.
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San Antonio and Chicago flights
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Other flights from San Antonio
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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 May 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$213 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$98 | Average$247 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$217 | Average$377 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$256 | Average$400 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$261 | Average$431 | FlexibilityNo cancel fee | On-time69% |