$113+ 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — CHI
Jul 7 — Jul 141
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 June 7, 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 June 7, 2026.
This United Airlines deal was found by Cheapflights users on 6/2. 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.
Wed 6/241:20 pm
SAT
- ORD
Nonstop3h 09m
United Airlines
Tue 6/301:30 pm
ORD
- SAT
Nonstop2h 59m
United Airlines
Deal found 6/2![United Airlines logo]()
$305
This Southwest deal was found by Cheapflights users on 6/2. 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 7/142:00 pm
SAT
- MDW
Nonstop2h 40m
Southwest
Tue 7/219:00 pm
MDW
- SAT
Nonstop2h 45m
Southwest
Deal found 6/2![Southwest logo]()
$305
This American Airlines deal was found by Cheapflights users on 6/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/232:10 pm
SAT
- ORD
Nonstop3h 02m
American Airlines
Tue 6/3010:30 am
ORD
- SAT
Nonstop3h 00m
American Airlines
Deal found 6/2![American Airlines logo]()
$306
This Super.com deal was found by Cheapflights users on 6/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/238:56 pm
SAT
- ORD
1 stop8h 11m
Frontier
Tue 7/79:57 pm
ORD
- SAT
1 stop20h 47m
Frontier
Deal found 6/4![Frontier logo]()
$307
This CheapOair deal was found by Cheapflights users on 6/5. 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.
Sun 7/197:39 pm
SAT
- ORD
1 stop25h 13m
Frontier
Wed 7/229:57 pm
ORD
- SAT
1 stop20h 47m
Frontier
Deal found 6/5![Frontier logo]()
$309
This Expedia deal was found by Cheapflights users on 6/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/237:39 pm
SAT
- ORD
1 stop25h 13m
Frontier
Tue 7/289:57 pm
ORD
- SAT
1 stop20h 47m
Frontier
Deal found 6/4![Frontier logo]()
$310
This Southwest deal was found by Cheapflights users on 6/5. 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 9/12:35 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Tue 9/151:55 pm
MDW
- SAT
1 stop4h 00m
Southwest
Deal found 6/5![Southwest logo]()
$311
This Booking.com deal was found by Cheapflights users on 6/4. 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.
Sun 8/99:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Tue 8/189:48 pm
ORD
- SAT
1 stop21h 08m
Frontier
Deal found 6/4![Frontier logo]()
$312
This Priceline deal was found by Cheapflights users on 6/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/258:56 pm
SAT
- ORD
1 stop8h 11m
Frontier
Sat 6/277:20 am
ORD
- SAT
1 stop12h 51m
Frontier
Deal found 6/2![Frontier logo]()
$313
This Frontier deal was found by Cheapflights users on 6/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/248:56 pm
SAT
- ORD
1 stop8h 11m
Frontier
Wed 7/17:20 am
ORD
- SAT
1 stop12h 51m
Frontier
Deal found 6/5![Frontier logo]()
$314
This United Airlines deal was found by Cheapflights users on 6/2. 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.
Tue 6/305:57 pm
SAT
- ORD
1 stop6h 48m
United Airlines
Wed 7/11:30 pm
ORD
- SAT
Nonstop2h 59m
United Airlines
Deal found 6/2![United Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 6/3. 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 7/141:20 pm
SAT
- MDW
1 stop5h 20m
Southwest
Wed 7/159:00 pm
MDW
- SAT
Nonstop2h 45m
Southwest
Deal found 6/3![Southwest logo]()
$315
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 June 7, 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 June 7, 2026.
This United Airlines deal was found by Cheapflights users on 6/3. 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.
Tue 7/145:32 pm
SAT
- ORD
Nonstop3h 01m
United Airlines
Wed 7/151:30 pm
ORD
- SAT
Nonstop2h 59m
United Airlines
Deal found 6/3![United Airlines logo]()
$305
This Southwest deal was found by Cheapflights users on 6/3. 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.
Sat 7/189:20 am
SAT
- MDW
2 stops7h 40m
Southwest
Tue 7/214:40 pm
MDW
- SAT
1 stop6h 40m
Southwest
Deal found 6/3![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 6/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:55 am
SAT
- MDW
1 stop8h 20m
Delta
Tue 9/86:00 am
MDW
- SAT
1 stop7h 07m
Delta
Deal found 6/3![Delta logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 6/248:56 pm
SAT
- RFD
1 stop15h 27m
Multiple Airlines
Mon 6/297:48 pm
RFD
- SAT
2 stops47h 08m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$578
This United Airlines deal was found by Cheapflights users on 6/5. 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 8/276:30 am
SAT
- ORD
Nonstop3h 00m
United Airlines
Mon 8/318:45 am
ORD
- SAT
Nonstop3h 07m
United Airlines
Deal found 6/5![United Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 6/3. 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.
Thu 7/96:25 am
SAT
- MDW
Nonstop2h 35m
Southwest
Mon 7/139:25 pm
MDW
- SAT
Nonstop2h 45m
Southwest
Deal found 6/3![Southwest logo]()
$367
This United Airlines deal was found by Cheapflights users on 6/3. 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.
Tue 7/146:40 am
SAT
- ORD
Nonstop2h 58m
United Airlines
Thu 7/169:25 am
ORD
- SAT
Nonstop3h 04m
United Airlines
Deal found 6/3![United Airlines logo]()
$336
This United Airlines deal was found by Cheapflights users on 6/3. 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 7/151:25 pm
SAT
- ORD
Nonstop3h 02m
United Airlines
Thu 7/169:25 am
ORD
- SAT
Nonstop3h 04m
United Airlines
Deal found 6/3![United Airlines logo]()
$336
This Southwest deal was found by Cheapflights users on 6/3. 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.
Sat 7/45:30 am
SAT
- MDW
1 stop6h 25m
Southwest
Mon 7/69:25 pm
MDW
- SAT
Nonstop2h 45m
Southwest
Deal found 6/3![Southwest logo]()
$377
This Southwest deal was found by Cheapflights users on 6/2. 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.
Mon 7/135:25 pm
SAT
- MDW
1 stop4h 35m
Southwest
Thu 7/169:25 pm
MDW
- SAT
Nonstop2h 45m
Southwest
Deal found 6/2![Southwest logo]()
$377
This United Airlines deal was found by Cheapflights users on 6/3. 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.
Thu 9/36:36 am
SAT
- ORD
Nonstop3h 00m
United Airlines
Mon 9/77:50 pm
ORD
- SAT
Nonstop3h 01m
United Airlines
Deal found 6/3![United Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 6/6. 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 7/165:15 am
SAT
- MDW
1 stop7h 23m
Delta
Wed 7/229:54 am
MDW
- SAT
1 stop7h 17m
Delta
Deal found 6/6![Delta logo]()
$472
This United Airlines deal was found by Cheapflights users on 6/5. 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.
Fri 7/106:40 am
SAT
- ORD
Nonstop2h 58m
United Airlines
Tue 7/149:25 am
ORD
- SAT
Nonstop3h 04m
United Airlines
Deal found 6/5![United Airlines logo]()
$356
This Southwest deal was found by Cheapflights users on 6/6. 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 7/95:40 am
SAT
- MDW
2 stops6h 30m
Southwest
Tue 7/147:45 am
MDW
- SAT
2 stops6h 50m
Southwest
Deal found 6/6![Southwest logo]()
$417
This United Airlines deal was found by Cheapflights users on 6/3. 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.
Sat 7/181:25 pm
SAT
- ORD
Nonstop3h 02m
United Airlines
Sat 8/17:58 pm
ORD
- SAT
Nonstop2h 59m
United Airlines
Deal found 6/3![United Airlines logo]()
$367
This Southwest deal was found by Cheapflights users on 6/4. 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.
Sat 6/279:20 am
SAT
- MDW
2 stops7h 40m
Southwest
Tue 6/306:30 am
MDW
- SAT
1 stop4h 40m
Southwest
Deal found 6/4![Southwest logo]()
$436
This United Airlines deal was found by Cheapflights users on 6/6. 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 8/125:27 pm
SAT
- ORD
Nonstop3h 00m
United Airlines
Sat 8/151:30 pm
ORD
- SAT
Nonstop3h 01m
United Airlines
Deal found 6/6![United Airlines logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 7/48:56 pm
SAT
- RFD
1 stop15h 28m
Multiple Airlines
Mon 7/67:50 pm
RFD
- SAT
2 stops22h 54m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$666
This Southwest deal was found by Cheapflights users on 6/6. 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.
Fri 7/243:20 pm
SAT
- MDW
Nonstop2h 35m
Southwest
Sun 7/269:40 pm
MDW
- SAT
Nonstop2h 45m
Southwest
Deal found 6/6![Southwest logo]()
$437
This United Airlines deal was found by Cheapflights users on 6/2. 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.
Fri 7/246:40 am
SAT
- ORD
Nonstop2h 58m
United Airlines
Mon 8/107:58 pm
ORD
- SAT
Nonstop2h 59m
United Airlines
Deal found 6/2![United Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 6/3. 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 6/167:51 pm
SAT
- RFD
2 stops24h 09m
Multiple Airlines
Fri 6/197:53 pm
RFD
- SAT
1 stop19h 44m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$695
This Southwest deal was found by Cheapflights users on 6/3. 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.
Fri 7/106:30 pm
SAT
- MDW
1 stop4h 35m
Southwest
Sun 7/129:40 pm
MDW
- SAT
Nonstop2h 45m
Southwest
Deal found 6/3![Southwest logo]()
$447
This United Airlines deal was found by Cheapflights users on 6/2. 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.
Sat 7/49:37 am
SAT
- ORD
1 stop5h 14m
United Airlines
Mon 7/67:58 pm
ORD
- SAT
Nonstop2h 59m
United Airlines
Deal found 6/2![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 6/2. 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.
Fri 7/36:30 pm
SAT
- MDW
1 stop4h 30m
Southwest
Sun 7/55:25 am
MDW
- SAT
1 stop6h 30m
Southwest
Deal found 6/2![Southwest logo]()
$447
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
Fri 6/194:22 pm
SAT
- RFD
1 stop16h 55m
Multiple Airlines
Mon 6/227:53 pm
RFD
- SAT
2 stops23h 03m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$726
This United Airlines deal was found by Cheapflights users on 6/6. 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 10/72:00 pm
SAT
- ORD
Nonstop3h 00m
United Airlines
Wed 10/212:30 pm
ORD
- SAT
1 stop6h 12m
United Airlines
Deal found 6/6![United Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 6/264:22 pm
SAT
- RFD
1 stop16h 55m
Multiple Airlines
Sun 6/2811:27 am
RFD
- SAT
2 stops23h 23m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$728
This Southwest deal was found by Cheapflights users on 6/6. 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 6/305:30 am
SAT
- MDW
2 stops6h 40m
Southwest
Tue 7/77:45 am
MDW
- SAT
2 stops6h 50m
Southwest
Deal found 6/6![Southwest logo]()
$472
Last-minute flights from San Antonio to ChicagoDiscover last-minute flight deals from San Antonio to Chicago. Data last updated June 7, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Chicago. Data last updated June 7, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 6/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/198:56 pm
SAT
- ORD
1 stop8h 11m
Frontier
Sun 6/219:48 pm
ORD
- SAT
1 stop21h 08m
Frontier
Deal found 6/2![Frontier logo]()
$317
This American Airlines deal was found by Cheapflights users on 6/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/232:10 pm
SAT
- ORD
Nonstop3h 02m
American Airlines
Tue 6/3010:30 am
ORD
- SAT
Nonstop3h 00m
American Airlines
Deal found 6/2![American Airlines logo]()
$306
This Super.com deal was found by Cheapflights users on 6/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/238:56 pm
SAT
- ORD
1 stop8h 11m
Frontier
Tue 7/79:57 pm
ORD
- SAT
1 stop20h 47m
Frontier
Deal found 6/4![Frontier logo]()
$307
This Frontier deal was found by Cheapflights users on 6/3. 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.
Tue 6/238:56 pm
SAT
- ORD
1 stop8h 11m
Frontier
Tue 6/307:20 am
ORD
- SAT
1 stop12h 51m
Frontier
Deal found 6/3![Frontier logo]()
$316
This United Airlines deal was found by Cheapflights users on 6/2. 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.
Wed 6/241:20 pm
SAT
- ORD
Nonstop3h 09m
United Airlines
Tue 6/301:30 pm
ORD
- SAT
Nonstop2h 59m
United Airlines
Deal found 6/2![United Airlines logo]()
$305
This Frontier deal was found by Cheapflights users on 6/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/248:56 pm
SAT
- ORD
1 stop8h 11m
Frontier
Wed 7/17:20 am
ORD
- SAT
1 stop12h 51m
Frontier
Deal found 6/5![Frontier logo]()
$314
This Priceline deal was found by Cheapflights users on 6/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/258:56 pm
SAT
- ORD
1 stop8h 11m
Frontier
Sat 6/277:20 am
ORD
- SAT
1 stop12h 51m
Frontier
Deal found 6/2![Frontier logo]()
$313
This United Airlines deal was found by Cheapflights users on 6/2. 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.
Tue 6/305:57 pm
SAT
- ORD
1 stop6h 48m
United Airlines
Wed 7/11:30 pm
ORD
- SAT
Nonstop2h 59m
United Airlines
Deal found 6/2![United Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 6/3. 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 7/142:00 pm
SAT
- MDW
Nonstop2h 40m
Southwest
Wed 7/159:00 pm
MDW
- SAT
Nonstop2h 45m
Southwest
Deal found 6/3![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 6/2. 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 7/142:00 pm
SAT
- MDW
Nonstop2h 40m
Southwest
Tue 7/216:30 am
MDW
- SAT
1 stop6h 15m
Southwest
Deal found 6/2![Southwest logo]()
$315
This CheapOair deal was found by Cheapflights users on 6/5. 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.
Sun 7/197:39 pm
SAT
- ORD
1 stop25h 13m
Frontier
Wed 7/229:57 pm
ORD
- SAT
1 stop20h 47m
Frontier
Deal found 6/5![Frontier logo]()
$309
This Expedia deal was found by Cheapflights users on 6/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/237:39 pm
SAT
- ORD
1 stop25h 13m
Frontier
Tue 7/289:57 pm
ORD
- SAT
1 stop20h 47m
Frontier
Deal found 6/4![Frontier logo]()
$310
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 June 7, 2026.
Search for one-way flight options from San Antonio to Chicago. Find affordable one-way fares based on user searches. Data last updated June 7, 2026.
This Super.com deal was found by Cheapflights users on 6/5. 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.
Wed 7/299:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/5![Frontier logo]()
$113
This Super.com deal was found by Cheapflights users on 6/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/238:56 pm
SAT
- ORD
1 stop8h 11m
Frontier
Deal found 6/2![Frontier logo]()
$114
This Frontier deal was found by Cheapflights users on 6/4. 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.
Wed 8/59:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/4![Frontier logo]()
$115
This Frontier deal was found by Cheapflights users on 6/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:56 pm
SAT
- ORD
1 stop8h 11m
Frontier
Deal found 6/2![Frontier logo]()
$116
This CheapOair deal was found by Cheapflights users on 6/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1312:16 pm
SAT
- ORD
1 stop21h 45m
Frontier
Deal found 6/6![Frontier logo]()
$126
This Super.com deal was found by Cheapflights users on 6/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/259:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/4![Frontier logo]()
$127
This Frontier deal was found by Cheapflights users on 6/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/44:22 pm
SAT
- ORD
1 stop6h 57m
Frontier
Deal found 6/7![Frontier logo]()
$129
This Super.com deal was found by Cheapflights users on 6/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/209:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/6![Frontier logo]()
$133
This Frontier deal was found by Cheapflights users on 6/4. 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.
Thu 7/99:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/4![Frontier logo]()
$134
This Frontier deal was found by Cheapflights users on 6/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/319:32 pm
SAT
- ORD
1 stop8h 05m
Frontier
Deal found 6/6![Frontier logo]()
$135
This Super.com deal was found by Cheapflights users on 6/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/167:51 pm
SAT
- ORD
1 stop24h 52m
Frontier
Deal found 6/2![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 6/2. 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.
Tue 6/237:51 pm
SAT
- MDW
2 stops26h 20m
Frontier
Deal found 6/2![Frontier logo]()
$147
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 June 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $305 (United Airlines) |
One-way from | $113 (Super.com) |
Popular in | December |
Cheapest in | September |
Average price | $379 |
Good round-trip deal | $357 or less |
Good one-way deal | $213 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 June 7, 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
Tue 7/14
5:32 pm-8:33 pm
Nonstop3h 01m
Chicago O'Hare Intl
Wed 7/15
1:30 pm-4:29 pm
Nonstop2h 59m
$305
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Thu 8/27
6:30 am-9:30 am
Nonstop3h 00m
Chicago O'Hare Intl
Mon 8/31
8:45 am-11:52 am
Nonstop3h 07m
$335
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Tue 7/14
6:40 am-9:38 am
Nonstop2h 58m
Chicago O'Hare Intl
Thu 7/16
9:25 am-12:29 pm
Nonstop3h 04m
$336
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Wed 7/15
1:25 pm-4:27 pm
Nonstop3h 02m
Chicago O'Hare Intl
Thu 7/16
9:25 am-12:29 pm
Nonstop3h 04m
$336
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Thu 9/3
6:36 am-9:36 am
Nonstop3h 00m
Chicago O'Hare Intl
Mon 9/7
7:50 pm-10:51 pm
Nonstop3h 01m
$347
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Fri 7/10
6:40 am-9:38 am
Nonstop2h 58m
Chicago O'Hare Intl
Tue 7/14
9:25 am-12:29 pm
Nonstop3h 04m
$356
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Sat 7/18
9:20 am-5:00 pm
2 stops7h 40m
Chicago Midway
Tue 7/21
4:40 pm-11:20 pm
1 stop6h 40m
$361
Quickest round-trip
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Thu 7/9
6:25 am-9:00 am
Nonstop2h 35m
Chicago Midway
Mon 7/13
9:25 pm-12:10 am
Nonstop2h 45m
$367
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Sat 7/18
1:25 pm-4:27 pm
Nonstop3h 02m
Chicago O'Hare Intl
Sat 8/1
7:58 pm-10:57 pm
Nonstop2h 59m
$367
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Wed 8/12
5:27 pm-8:27 pm
Nonstop3h 00m
Chicago O'Hare Intl
Sat 8/15
1:30 pm-4:31 pm
Nonstop3h 01m
$367
Showing 1-10 of 58 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 June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price 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
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 $230). 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 June 7, 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 June 7, 2026.
The most flights from SAT to CHI are scheduled on a Thursday (34 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).
How much does it cost to fly round-trip from San Antonio to Chicago?
How far ahead should I book a flight from San Antonio to Chicago?
To ensure you get the cheapest price possible for a flight from San Antonio to Chicago, you should look to book at least 69 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
The best insider tips for San Antonio to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your San Antonio to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 7, 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.
Entertainment
7.5
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
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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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 7, 2026.
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San Antonio and Chicago flights
Browse other San Antonio and Chicago flight options. Last updated on June 7, 2026.
Other flights from San Antonio
Browse through other flights departing from San Antonio. Flights are based on user searches made on Cheapflights and were last updated on June 7, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from San Antonio to Chicago
Discover the top 4 airlines that operate flights from San Antonio to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$213 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$388 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$256 | Average$404 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$277 | Average$437 | FlexibilityNo cancel fee | On-time69% |