$89+ Cheap flights from Chicago (CHI) to San Antonio (SAT)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAT
Sep 20 — Sep 271
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to San Antonio with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to San Antonio are usually found in October or June, booked 47 days in advance, depart on a Tuesday or Thursday and return on a Thursday
Cheap flight deals from Chicago to San Antonio
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to San AntonioExplore the most affordable flight options available from Chicago to San Antonio. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
Explore the most affordable flight options available from Chicago to San Antonio. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
This Frontier deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/266:30 am -
1 stop12h 55m
Wed 9/303:19 pm -
1 stop14h 19m
Deal found 8/20![Frontier logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/236:30 am -
1 stop12h 55m
Mon 9/289:50 pm -
2 stops26h 33m
Deal found 8/18![Frontier logo]()
$263
This CheapOair deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/96:30 am -
1 stop12h 56m
Thu 10/158:21 pm -
1 stop28h 03m
Deal found 8/20![Frontier logo]()
$264
This Frontier deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 8/219:10 pm -
1 stop11h 46m
Wed 9/910:03 am -
1 stop12h 56m
Deal found 8/19![Frontier logo]()
$265
This American Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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.
Fri 9/1111:08 am -
Nonstop2h 51m
Thu 9/173:02 pm -
Nonstop3h 05m
Deal found 8/20![American Airlines logo]()
$266
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/1912:47 pm -
1 stop7h 06m
Tue 9/221:00 pm -
Nonstop3h 00m
Deal found 8/18![United Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 11/96:30 pm -
1 stop5h 35m
Wed 11/119:50 am -
Nonstop2h 30m
Deal found 8/18![Southwest logo]()
$267
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 11/67:45 pm -
Nonstop3h 08m
Mon 11/96:37 am -
Nonstop2h 59m
Deal found 8/17![United Airlines logo]()
$268
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 10/138:45 pm -
Nonstop2h 45m
Fri 10/162:35 pm -
Nonstop2h 40m
Deal found 8/18![Southwest logo]()
$268
This CheapOair deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 8/307:44 pm -
1 stop13h 12m
Tue 9/88:26 pm -
1 stop27h 57m
Deal found 8/17![Frontier logo]()
$269
This Kissandfly.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:08 pm -
Nonstop3h 01m
Mon 9/148:20 pm -
1 stop28h 03m
Deal found 8/18![Frontier logo]()
$270
This Booking.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:41 pm -
1 stop28h 50m
Wed 9/163:19 pm -
1 stop14h 19m
Deal found 8/17![Frontier logo]()
$271
Best flights from Chicago to San AntonioDiscover carefully curated flight deals from Chicago to San Antonio that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
Discover carefully curated flight deals from Chicago to San Antonio that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 10/315:30 am -
2 stops7h 40m
Wed 11/42:40 pm -
Nonstop2h 35m
Deal found 8/19![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 10/21:51 pm -
1 stop7h 28m
Mon 10/511:36 am -
1 stop6h 50m
Deal found 8/17![Delta logo]()
$288
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/87:50 pm -
Nonstop3h 01m
Fri 9/114:39 pm -
1 stop6h 06m
Deal found 8/17![United Airlines logo]()
$301
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 11/54:50 pm -
2 stops6h 35m
Mon 11/92:50 pm -
Nonstop2h 35m
Deal found 8/18![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 10/157:15 am -
1 stop6h 40m
Tue 10/2012:55 pm -
2 stops6h 30m
Deal found 8/15![Southwest logo]()
$282
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 9/2312:59 pm -
Nonstop3h 01m
Sat 9/265:33 pm -
Nonstop3h 00m
Deal found 8/16![United Airlines logo]()
$347
This Alaska Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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.
Sat 11/142:07 pm -
2 stops26h 12m
Thu 11/195:29 pm -
1 stop12h 11m
Deal found 8/16![Alaska Airlines logo]()
$769
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/210:48 am -
1 stop7h 58m
Sun 10/411:36 am -
1 stop6h 57m
Deal found 8/16![Delta logo]()
$409
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/35:10 am -
2 stops8h 30m
Wed 10/712:55 pm -
2 stops6h 30m
Deal found 8/16![Southwest logo]()
$343
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 8/267:50 pm -
Nonstop3h 00m
Wed 9/166:30 am -
Nonstop3h 00m
Deal found 8/17![United Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 10/19:45 am -
Nonstop2h 45m
Sun 10/43:35 pm -
Nonstop2h 40m
Deal found 8/15![Southwest logo]()
$355
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/109:00 am -
Nonstop3h 06m
Mon 10/125:30 pm -
Nonstop3h 01m
Deal found 8/20![United Airlines logo]()
$403
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/188:35 pm -
Nonstop2h 45m
Sun 9/203:50 pm -
1 stop4h 45m
Deal found 8/17![Southwest logo]()
$376
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/35:30 am -
1 stop8h 08m
Sun 9/65:15 am -
1 stop5h 27m
Deal found 8/18![Delta logo]()
$509
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 10/239:20 pm -
Nonstop2h 45m
Sun 10/259:20 am -
Nonstop2h 40m
Deal found 8/18![Southwest logo]()
$378
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/38:45 am -
Nonstop3h 07m
Sun 9/65:30 pm -
Nonstop3h 00m
Deal found 8/17![United Airlines logo]()
$489
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/245:25 am -
1 stop5h 45m
Sun 9/277:15 am -
2 stops6h 35m
Deal found 8/20![Southwest logo]()
$392
This Alaska Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Sat 9/261:03 pm -
1 stop27h 16m
Tue 9/295:29 pm -
2 stops19h 53m
Deal found 8/18![Alaska Airlines logo]()
$813
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/47:30 am -
1 stop6h 10m
Tue 9/82:50 pm -
Nonstop2h 35m
Deal found 8/17![Southwest logo]()
$420
This Alaska Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Tue 11/32:15 pm -
2 stops26h 04m
Fri 11/65:29 pm -
2 stops19h 40m
Deal found 8/18![Alaska Airlines logo]()
$816
Last-minute flights from Chicago to San AntonioDiscover last-minute flight deals from Chicago to San Antonio. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San Antonio. Data last updated August 21, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 8/219:10 pm -
1 stop11h 46m
Wed 9/910:03 am -
1 stop12h 56m
Deal found 8/19![Frontier logo]()
$265
This Booking.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:41 pm -
1 stop28h 50m
Wed 9/163:19 pm -
1 stop14h 19m
Deal found 8/17![Frontier logo]()
$271
This CheapOair deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 8/307:44 pm -
1 stop13h 12m
Tue 9/88:26 pm -
1 stop27h 57m
Deal found 8/17![Frontier logo]()
$269
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/105:30 am -
1 stop5h 05m
Mon 9/145:00 am -
Nonstop2h 35m
Deal found 8/18![Southwest logo]()
$267
This Kissandfly.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:08 pm -
Nonstop3h 01m
Mon 9/148:20 pm -
1 stop28h 03m
Deal found 8/18![Frontier logo]()
$270
This American Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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.
Fri 9/1111:08 am -
Nonstop2h 51m
Thu 9/173:02 pm -
Nonstop3h 05m
Deal found 8/20![American Airlines logo]()
$266
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/118:35 pm -
Nonstop2h 45m
Tue 9/152:50 pm -
Nonstop2h 35m
Deal found 8/20![Southwest logo]()
$268
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Fri 9/183:08 pm -
Nonstop3h 01m
Sat 9/193:02 pm -
Nonstop3h 05m
Deal found 8/18![American Airlines logo]()
$268
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/1912:47 pm -
1 stop7h 06m
Tue 9/221:00 pm -
Nonstop3h 00m
Deal found 8/18![United Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/236:30 am -
1 stop12h 55m
Mon 9/289:50 pm -
2 stops26h 33m
Deal found 8/18![Frontier logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/236:30 am -
1 stop12h 55m
Sun 9/279:25 am -
2 stops37h 34m
Deal found 8/18![Multiple Airlines logo]()
$274
This Frontier deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/266:30 am -
1 stop12h 55m
Wed 9/303:19 pm -
1 stop14h 19m
Deal found 8/20![Frontier logo]()
$258
One-way flights from Chicago to San AntonioSearch for one-way flight options from Chicago to San Antonio. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
Search for one-way flight options from Chicago to San Antonio. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This Frontier deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 11/161:02 pm -
1 stop7h 54m
Deal found 8/17![Frontier logo]()
$89
This Super.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/218:55 pm -
1 stop17h 25m
Deal found 8/18![Frontier logo]()
$94
This Frontier deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/156:30 am -
1 stop12h 55m
Deal found 8/17![Frontier logo]()
$95
This CheapOair deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 10/13:50 pm -
1 stop17h 20m
Deal found 8/19![Frontier logo]()
$96
This CheapOair deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 10/3111:06 am -
1 stop24h 06m
Deal found 8/17![Frontier logo]()
$100
This Trip.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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.
Sat 10/36:30 am -
1 stop12h 55m
Deal found 8/19![Frontier logo]()
$102
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/188:55 pm -
1 stop16h 53m
Deal found 8/19![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 10/236:30 am -
1 stop12h 56m
Deal found 8/17![Frontier logo]()
$106
This CheapOair deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 10/28:55 pm -
1 stop16h 53m
Deal found 8/18![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:55 pm -
1 stop17h 25m
Deal found 8/19![Frontier logo]()
$110
This CheapOair deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 11/611:06 am -
1 stop23h 06m
Deal found 8/18![Frontier logo]()
$111
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/158:30 pm -
Nonstop2h 45m
Deal found 8/18![Southwest logo]()
$129
Find flight deals from Chicago to San Antonio
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to San Antonio (SAT). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $258 (Frontier) |
One-way from | $89 (Frontier) |
Popular in | August |
Cheapest in | October |
Average price | $433 |
Good round-trip deal | $360 or less |
Good one-way deal | $161 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to San Antonio that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 21, 2026.
Use the filters below to find and compare flights from Chicago to San Antonio that are best for you.
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Route
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Cheapest round-trip
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Sat 10/31
5:30 am-1:10 pm
2 stops7h 40m
San Antonio
Wed 11/4
2:40 pm-5:15 pm
Nonstop2h 35m
$272
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Thu 11/5
4:50 pm-11:25 pm
2 stops6h 35m
San Antonio
Mon 11/9
2:50 pm-5:25 pm
Nonstop2h 35m
$272
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Thu 10/15
7:15 am-1:55 pm
1 stop6h 40m
San Antonio
Tue 10/20
12:55 pm-7:25 pm
2 stops6h 30m
$282
ChicagoSan Antonio
ORD Chicago O'Hare Intl - SAT San Antonio
ORDSAT
Chicago O'Hare Intl
Fri 10/2
1:51 pm-9:19 pm
1 stop7h 28m
San Antonio
Mon 10/5
11:36 am-6:26 pm
1 stop6h 50m
$288
ChicagoSan Antonio
ORD Chicago O'Hare Intl - SAT San Antonio
ORDSAT
Chicago O'Hare Intl
Tue 9/8
7:50 pm-10:51 pm
Nonstop3h 01m
San Antonio
Fri 9/11
4:39 pm-10:45 pm
1 stop6h 06m
$301
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Sat 10/3
5:10 am-1:40 pm
2 stops8h 30m
San Antonio
Wed 10/7
12:55 pm-7:25 pm
2 stops6h 30m
$343
ChicagoSan Antonio
ORD Chicago O'Hare Intl - SAT San Antonio
ORDSAT
Chicago O'Hare Intl
Wed 9/23
12:59 pm-4:00 pm
Nonstop3h 01m
San Antonio
Sat 9/26
5:33 pm-8:33 pm
Nonstop3h 00m
$347
Quickest round-trip
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Thu 10/1
9:45 am-12:30 pm
Nonstop2h 45m
San Antonio
Sun 10/4
3:35 pm-6:15 pm
Nonstop2h 40m
$355
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Fri 9/18
8:35 pm-11:20 pm
Nonstop2h 45m
San Antonio
Sun 9/20
3:50 pm-8:35 pm
1 stop4h 45m
$376
ChicagoSan Antonio
MDW Chicago Midway - SAT San Antonio
MDWSAT
Chicago Midway
Fri 10/23
9:20 pm-12:05 am
Nonstop2h 45m
San Antonio
Sun 10/25
9:20 am-12:00 pm
Nonstop2h 40m
$378
Showing 1-10 of 44 resultsSorted by cheapest first
Compare providers for flights from Chicago to San Antonio
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to San Antonio in August.
| 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 Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-San Antonio flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-San Antonio flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-San Antonio flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-San Antonio flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-San Antonio flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to San Antonio
Have a flexible travel schedule? Discover the best time to fly to San Antonio from Chicago with our price prediction graph.
CHI-SAT
ORD-SAT
MDW-SAT
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to San Antonio
CHI-SAT
ORD-SAT
MDW-SAT
What is the cheapest month to book a flight from Chicago to San Antonio?
Currently, October is the cheapest month in which you can book a flight from Chicago to San Antonio (average of $341). Flying from Chicago to San Antonio in March is currently the most expensive (average of $434). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to SAT?
Find hourly flight availability from Chicago to San Antonio. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 21, 2026.
It’s typically best to fly out from Chicago to San Antonio in the evening. Doing so could potentially save you 2% on the flight price compared to flying in the morning, which is usually more expensive.
Weekly flight availability from Chicago to San Antonio
Explore weekly flight availability from Chicago to San Antonio. 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 August 21, 2026.
The most flights from CHI to SAT are scheduled on a Wednesday (27 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).
How much does it cost to fly round-trip from Chicago to San Antonio?
Airfare is below average for this route at the moment.
Chicago to San Antonio flights typically cost between $330 and $497 in September.The cheapest round-trip price found within the last 5 days was $258 on Frontier (Sep 26-Sep 29).
How far ahead should I book a flight from Chicago to San Antonio?
Booking 48 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San Antonio. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Chicago to San Antonio?
Use this chart to determine the cheapest time to fly round-trip from Chicago to San Antonio. Price data was last updated on August 15, 2026.
Travelers seeking maximum savings on their Chicago to San Antonio flight should consider departing on Friday afternoons when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Chicago to San Antonio flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to San Antonio trip
Our travel experts
Reviews of airlines servicing San Antonio
Get insights into the airlines that provide service to San Antonio. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Antonio. Reviews last updated August 21, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Chicago to San Antonio. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to San Antonio. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near San Antonio?
Book flights to San Antonio if you plan to visit one of these locationsNew Braunfels
Kerrville
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Chicago and San Antonio flights
Browse other Chicago and San Antonio flight options. Last updated on August 21, 2026.
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Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on August 21, 2026.
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Explore flights to San Antonio departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 21, 2026.
Top 4 airlines flying from Chicago to San Antonio
Discover the top 4 airlines that operate flights from Chicago to San Antonio. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$101 | Average$226 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$224 | Average$429 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$277 | Average$427 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$305 | Average$447 | FlexibilityNo cancel fee | On-time63% |