$128+ Cheap flights from San Antonio (SAT) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — CHI
Oct 7 — Oct 141
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 February or April, booked 53 days in advance, depart on a Thursday or Friday and return on a Thursday
Cheap flight deals from San Antonio to Chicago
Cheapest
Best
Last-minute
One-way
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 September 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 September 7, 2026.
This CheapOair deal was found by Cheapflights users on 9/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:39 pm -
1 stop16h 59m
Sun 9/278:55 pm -
1 stop14h 49m
Deal found 9/2![Frontier logo]()
$268
This CheapOair deal was found by Cheapflights users on 9/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/189:50 pm -
1 stop7h 48m
Mon 9/288:55 pm -
1 stop17h 25m
Deal found 9/2![Frontier logo]()
$271
This Super.com deal was found by Cheapflights users on 9/2. 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.
Thu 9/178:20 pm -
1 stop28h 03m
Sun 9/203:50 pm -
1 stop17h 20m
Deal found 9/2![Frontier logo]()
$272
This CheapOair deal was found by Cheapflights users on 9/3. 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.
Sat 9/262:47 pm -
1 stop14h 51m
Mon 9/288:55 pm -
1 stop17h 25m
Deal found 9/3![Frontier logo]()
$276
This Frontier deal was found by Cheapflights users on 9/2. 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.
Fri 10/2310:03 am -
1 stop8h 59m
Mon 10/266:30 am -
1 stop12h 56m
Deal found 9/2![Frontier logo]()
$277
This Frontier deal was found by Cheapflights users on 9/2. 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.
Mon 9/289:50 pm -
1 stop7h 48m
Fri 10/26:30 am -
1 stop12h 55m
Deal found 9/2![Frontier logo]()
$278
This CheapOair deal was found by Cheapflights users on 9/3. 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.
Sat 10/108:21 pm -
1 stop28h 03m
Sat 10/176:30 am -
1 stop12h 56m
Deal found 9/3![Frontier logo]()
$279
This Frontier deal was found by Cheapflights users on 9/5. 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.
Fri 9/189:50 pm -
1 stop7h 48m
Tue 9/226:30 am -
1 stop12h 55m
Deal found 9/5![Frontier logo]()
$280
This Trip.com deal was found by Cheapflights users on 9/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/208:20 pm -
1 stop28h 03m
Sun 9/273:50 pm -
1 stop17h 20m
Deal found 9/7![Frontier logo]()
$281
This Super.com deal was found by Cheapflights users on 9/6. 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.
Fri 9/189:50 pm -
1 stop7h 48m
Mon 9/218:55 pm -
1 stop17h 25m
Deal found 9/6![Frontier logo]()
$286
This Southwest deal was found by Cheapflights users on 9/2. 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.
Wed 10/72:25 pm -
Nonstop2h 40m
Wed 10/148:45 pm -
Nonstop2h 50m
Deal found 9/2![Southwest logo]()
$365
This Southwest deal was found by Cheapflights users on 9/2. 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 10/272:25 pm -
Nonstop2h 40m
Sat 10/319:10 am -
1 stop4h 00m
Deal found 9/2![Southwest logo]()
$371
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 September 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 September 7, 2026.
This Southwest deal was found by Cheapflights users on 9/3. 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 10/711:25 am -
2 stops5h 45m
Mon 10/129:20 pm -
Nonstop2h 50m
Deal found 9/3![Southwest logo]()
$380
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Fri 9/256:35 am -
Nonstop3h 00m
Tue 9/2910:32 am -
1 stop5h 21m
Deal found 9/3![United Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 9/2412:39 pm -
1 stop8h 00m
Sun 9/279:29 pm -
1 stop14h 15m
Deal found 9/2![Multiple Airlines logo]()
$437
This KAYAK deal was found by Cheapflights users on 9/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2811:36 am -
1 stop6h 57m
Fri 10/29:29 am -
1 stop6h 24m
Deal found 9/2![Delta logo]()
$442
This Southwest deal was found by Cheapflights users on 9/2. 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 10/235:40 am -
1 stop5h 30m
Mon 10/266:30 pm -
1 stop6h 15m
Deal found 9/2![Southwest logo]()
$400
This Alaska Airlines deal was found by Cheapflights users on 9/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:26 pm -
2 stops19h 59m
Mon 10/265:46 pm -
1 stop22h 30m
Deal found 9/6![Alaska Airlines logo]()
$848
This Southwest deal was found by Cheapflights users on 9/2. 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 9/256:10 pm -
1 stop5h 40m
Mon 9/288:35 pm -
Nonstop2h 45m
Deal found 9/2![Southwest logo]()
$426
This United Airlines deal was found by Cheapflights users on 9/2. 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 9/105:30 pm -
Nonstop2h 59m
Mon 9/145:53 pm -
1 stop4h 51m
Deal found 9/2![United Airlines logo]()
$523
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Sun 11/19:25 am -
2 stops24h 29m
Thu 11/58:52 pm -
1 stop24h 42m
Deal found 9/4![Multiple Airlines logo]()
$524
This Southwest deal was found by Cheapflights users on 9/5. 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.
Wed 10/72:25 pm -
Nonstop2h 40m
Sun 10/119:25 pm -
Nonstop2h 50m
Deal found 9/5![Southwest logo]()
$435
This KAYAK deal was found by Cheapflights users on 9/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/275:15 am -
1 stop5h 22m
Fri 10/28:55 am -
1 stop6h 58m
Deal found 9/2![Delta logo]()
$531
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Thu 10/89:25 am -
2 stops22h 37m
Sun 10/119:33 pm -
1 stop14h 42m
Deal found 9/5![Multiple Airlines logo]()
$524
This Southwest deal was found by Cheapflights users on 9/3. 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 11/136:35 am -
1 stop5h 40m
Sun 11/1510:00 am -
Nonstop2h 50m
Deal found 9/3![Southwest logo]()
$440
This United Airlines deal was found by Cheapflights users on 9/2. 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.
Sun 9/275:30 am -
1 stop4h 46m
Fri 10/21:30 pm -
Nonstop3h 01m
Deal found 9/2![United Airlines logo]()
$539
This Southwest deal was found by Cheapflights users on 9/4. 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 10/1712:35 pm -
2 stops8h 25m
Sun 10/259:25 pm -
Nonstop2h 50m
Deal found 9/4![Southwest logo]()
$450
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Wed 10/78:20 pm -
2 stops23h 53m
Sun 10/119:33 pm -
1 stop14h 42m
Deal found 9/5![Multiple Airlines logo]()
$553
This United Airlines deal was found by Cheapflights users on 9/3. 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 9/171:00 pm -
Nonstop3h 00m
Tue 9/2212:59 pm -
Nonstop3h 01m
Deal found 9/3![United Airlines logo]()
$559
This Delta deal was found by Cheapflights users on 9/6. 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 9/1011:06 am -
1 stop5h 31m
Mon 9/145:30 am -
1 stop7h 19m
Deal found 9/6![Delta logo]()
$631
This Southwest deal was found by Cheapflights users on 9/5. 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.
Fri 11/62:50 pm -
Nonstop2h 35m
Sun 11/89:30 pm -
Nonstop2h 50m
Deal found 9/5![Southwest logo]()
$453
This United Airlines deal was found by Cheapflights users on 9/2. 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 10/77:35 am -
1 stop4h 50m
Fri 10/95:30 am -
1 stop5h 13m
Deal found 9/2![United Airlines logo]()
$571
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 9/1012:39 pm -
1 stop8h 00m
Sun 9/139:29 pm -
2 stops21h 56m
Deal found 9/2![Multiple Airlines logo]()
$618
This Southwest deal was found by Cheapflights users on 9/6. 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 10/96:45 pm -
1 stop6h 25m
Tue 10/1312:05 pm -
1 stop6h 20m
Deal found 9/6![Southwest logo]()
$467
This KAYAK deal was found by Cheapflights users on 9/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/283:09 pm -
2 stops22h 17m
Fri 10/22:22 pm -
2 stops33h 37m
Deal found 9/2![Alaska Airlines logo]()
$865
This United Airlines deal was found by Cheapflights users on 9/3. 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 9/121:00 pm -
Nonstop3h 00m
Wed 9/1612:59 pm -
Nonstop3h 01m
Deal found 9/3![United Airlines logo]()
$625
This Southwest deal was found by Cheapflights users on 9/4. 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.
Sun 10/49:20 am -
Nonstop2h 40m
Sun 10/119:25 pm -
Nonstop2h 50m
Deal found 9/4![Southwest logo]()
$473
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Thu 9/109:25 am -
2 stops23h 27m
Thu 9/179:29 pm -
1 stop14h 15m
Deal found 9/4![Multiple Airlines logo]()
$639
This Delta deal was found by Cheapflights users on 9/4. 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.
Fri 9/1811:36 am -
2 stops12h 23m
Mon 9/283:55 pm -
1 stop5h 27m
Deal found 9/4![Delta logo]()
$776
Last-minute flights from San Antonio to ChicagoDiscover last-minute flight deals from San Antonio to Chicago. Data last updated September 7, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Chicago. Data last updated September 7, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 9/3. 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.
Sat 9/128:20 pm -
1 stop28h 03m
Tue 9/223:50 pm -
1 stop17h 17m
Deal found 9/3![Frontier logo]()
$292
This CheapOair deal was found by Cheapflights users on 9/5. 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.
Sat 9/122:47 pm -
1 stop14h 51m
Tue 9/153:50 pm -
1 stop17h 17m
Deal found 9/5![Frontier logo]()
$310
This Frontier deal was found by Cheapflights users on 9/2. 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.
Mon 9/149:50 pm -
1 stop7h 48m
Wed 9/166:30 am -
1 stop12h 55m
Deal found 9/2![Frontier logo]()
$280
This Super.com deal was found by Cheapflights users on 9/4. 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.
Mon 9/148:20 pm -
1 stop28h 03m
Thu 9/1711:15 am -
1 stop21h 55m
Deal found 9/4![Frontier logo]()
$312
This Trip.com deal was found by Cheapflights users on 9/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:19 pm -
1 stop14h 19m
Wed 9/161:21 pm -
1 stop22h 23m
Deal found 9/2![Frontier logo]()
$296
This CheapOair deal was found by Cheapflights users on 9/3. 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.
Tue 9/158:20 pm -
1 stop28h 03m
Thu 9/173:50 pm -
1 stop17h 20m
Deal found 9/3![Frontier logo]()
$299
This Frontier deal was found by Cheapflights users on 9/6. 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.
Tue 9/153:19 pm -
1 stop14h 19m
Fri 9/186:30 am -
1 stop12h 55m
Deal found 9/6![Frontier logo]()
$300
This Expedia deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1610:03 am -
1 stop12h 56m
Wed 9/236:30 am -
1 stop12h 55m
Deal found 9/6![Frontier logo]()
$290
This Super.com deal was found by Cheapflights users on 9/2. 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.
Thu 9/178:20 pm -
1 stop28h 03m
Sun 9/203:50 pm -
1 stop17h 20m
Deal found 9/2![Frontier logo]()
$272
This CheapOair deal was found by Cheapflights users on 9/3. 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 9/178:20 pm -
1 stop28h 03m
Tue 9/226:30 am -
1 stop12h 55m
Deal found 9/3![Frontier logo]()
$278
This Southwest deal was found by Cheapflights users on 9/2. 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.
Wed 10/72:25 pm -
Nonstop2h 40m
Wed 10/148:45 pm -
Nonstop2h 50m
Deal found 9/2![Southwest logo]()
$365
This Southwest deal was found by Cheapflights users on 9/2. 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 10/272:25 pm -
Nonstop2h 40m
Sat 10/319:10 am -
1 stop4h 00m
Deal found 9/2![Southwest logo]()
$371
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 September 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 September 7, 2026.
This Super.com deal was found by Cheapflights users on 9/6. 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.
Fri 9/259:50 pm -
1 stop7h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$128
This Frontier deal was found by Cheapflights users on 9/3. 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.
Sat 12/512:00 pm -
1 stop7h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$129
This Frontier deal was found by Cheapflights users on 9/2. 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.
Fri 9/189:50 pm -
1 stop7h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$130
This Super.com deal was found by Cheapflights users on 9/5. 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.
Sat 10/108:21 pm -
1 stop28h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Frontier logo]()
$133
This Super.com deal was found by Cheapflights users on 9/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:20 pm -
1 stop28h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$134
This Expedia deal was found by Cheapflights users on 9/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/29:07 pm -
1 stop28h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$135
This Frontier deal was found by Cheapflights users on 9/3. 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 9/2310:03 am -
1 stop12h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$136
This Trip.com deal was found by Cheapflights users on 9/4. 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.
Wed 11/188:20 pm -
1 stop28h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$138
This Jetabroad deal was found by Cheapflights users on 9/3. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/73:19 pm -
1 stop13h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$140
This CheapOair deal was found by Cheapflights users on 9/3. 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.
Wed 12/29:07 pm -
1 stop21h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$140
This Super.com deal was found by Cheapflights users on 9/4. 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.
Fri 9/119:50 pm -
1 stop7h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$148
This Frontier deal was found by Cheapflights users on 9/3. 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.
Thu 12/312:00 pm -
1 stop7h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$149
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 September 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $268 (CheapOair) |
One-way from | $128 (Super.com) |
Popular in | June |
Cheapest in | February |
Average price | $367 |
Good round-trip deal | $344 or less |
Good one-way deal | $205 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 7,457,451 searches. Data last updated September 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 San Antonio - ORD Chicago O'Hare Intl
SATORD
San Antonio
Wed 10/21
2:00 pm-5:00 pm
Nonstop3h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$183
San AntonioChicago
SAT San Antonio - ORD Chicago O'Hare Intl
SATORD
San Antonio
Mon 10/26
6:37 am-9:36 am
Nonstop2h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$183
San AntonioChicago
SAT San Antonio - ORD Chicago O'Hare Intl
SATORD
San Antonio
Sat 2/20
10:45 am-4:37 pm
1 stop5h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$193
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Sat 10/3
2:20 pm-8:35 pm
1 stop6h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$193
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Mon 9/28
6:35 am-11:54 am
1 stop5h 19m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$193
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Tue 9/29
5:15 am-12:39 pm
1 stop7h 24m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$193
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Mon 10/5
4:21 pm-10:44 pm
1 stop6h 23m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$193
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Wed 9/30
6:00 am-1:20 pm
1 stop7h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$203
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Sat 12/5
7:38 am-3:05 pm
1 stop7h 27m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$203
San AntonioChicago
SAT San Antonio - RFD Chicago Greater Rockford
SATRFD
San Antonio
Wed 9/23
8:20 pm-4:15 pm
2 stops43h 55m
Chicago Greater Rockford
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$208
Showing 1-10 of 57 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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*3 stars |
- 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, February is the cheapest month in which you can book a flight from San Antonio to Chicago (average of $342). Flying from San Antonio to Chicago in June is currently the most expensive (average of $443). 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 September 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 26% versus a flight at noon.
How much does it cost to fly round-trip from San Antonio to Chicago?
Airfare is below average for this route at the moment.
San Antonio to Chicago flights typically cost between $297 and $434 in September.The cheapest round-trip price found within the last 5 days was $268 on Frontier (Sep 24-Sep 27).
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 September 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.
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from San Antonio to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from San Antonio
Popular flights
Top destinations
Alternative routes for San Antonio to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
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 September 7, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from San Antonio to Chicago by cabin class
Find flights from San Antonio to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
San Antonio and Chicago flights
Browse other San Antonio and Chicago flight options. Last updated on September 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 September 7, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
San Antonio to Chicago flights
Consider these flights traveling from San Antonio to Chicago.
Top 4 airlines flying from San Antonio to Chicago
Discover the top 4 airlines that operate flights from San Antonio to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$131 | Average$267 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$237 | Average$397 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$281 | Average$464 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$287 | Average$441 | FlexibilityNo cancel fee | On-time69% |