$98+ 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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — CHI
Nov 24 — Dec 11
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 19 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 October 25, 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 October 25, 2026.
This Mytrip deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/49:56 pm -
2 stops26h 58m
Sun 12/68:53 pm -
2 stops23h 09m
Deal found 10/24![Frontier logo]()
$319
This Mytrip deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1310:29 pm -
2 stops20h 01m
Mon 11/167:50 pm -
2 stops23h 35m
Deal found 10/22![Frontier logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/810:29 pm -
2 stops25h 52m
Thu 11/126:30 am -
1 stop12h 55m
Deal found 10/24![Frontier logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/68:11 pm -
1 stop28h 10m
Tue 11/107:35 pm -
2 stops23h 50m
Deal found 10/22![Frontier logo]()
$322
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/1411:30 am -
2 stops5h 55m
Mon 11/307:20 pm -
1 stop6h 05m
Deal found 10/22![Southwest logo]()
$322
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 12/17:09 am -
Nonstop2h 56m
Fri 1/14:53 pm -
1 stop7h 06m
Deal found 10/21![American Airlines logo]()
$323
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/123:35 pm -
1 stop4h 50m
Mon 11/168:50 pm -
Nonstop2h 55m
Deal found 10/21![Southwest logo]()
$323
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Tue 12/11:50 pm -
1 stop5h 38m
Fri 1/11:30 pm -
Nonstop3h 24m
Deal found 10/20![United Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/58:20 pm -
1 stop28h 01m
Mon 11/97:50 pm -
2 stops23h 35m
Deal found 10/21![Frontier logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/2310:11 pm -
1 stop30h 59m
Mon 12/710:37 pm -
2 stops19h 24m
Deal found 10/22![Frontier logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/810:29 pm -
2 stops25h 52m
Sat 11/146:30 am -
1 stop12h 55m
Deal found 10/23![Frontier logo]()
$328
This Mytrip deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:29 pm -
2 stops25h 18m
Mon 11/166:42 pm -
2 stops24h 43m
Deal found 10/22![Frontier logo]()
$328
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 October 25, 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 October 25, 2026.
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Mon 12/217:08 pm -
1 stop5h 36m
Fri 12/257:45 pm -
Nonstop3h 14m
Deal found 10/20![United Airlines logo]()
$324
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/246:25 am -
Nonstop2h 30m
Thu 12/38:50 pm -
Nonstop2h 55m
Deal found 10/22![Southwest logo]()
$355
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 12/172:29 pm -
1 stop5h 16m
Thu 12/245:00 pm -
1 stop6h 21m
Deal found 10/24![Delta logo]()
$377
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/106:35 am -
Nonstop2h 57m
Sun 12/137:45 pm -
Nonstop3h 07m
Deal found 10/23![United Airlines logo]()
$328
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/1111:25 am -
2 stops6h 15m
Sat 12/125:05 am -
1 stop6h 55m
Deal found 10/22![Southwest logo]()
$356
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 2/66:38 am -
Nonstop2h 57m
Sun 2/77:52 pm -
Nonstop3h 14m
Deal found 10/21![United Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/276:40 am -
1 stop8h 15m
Sat 12/55:02 pm -
1 stop5h 55m
Deal found 10/24![Delta logo]()
$377
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/115:30 am -
1 stop6h 59m
Sun 11/158:30 pm -
Nonstop3h 08m
Deal found 10/22![United Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Mon 12/75:16 am -
1 stop5h 12m
Thu 12/1710:24 am -
1 stop7h 14m
Deal found 10/21![Delta logo]()
$398
This Southwest deal was found by Cheapflights users on 10/20. 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.
Wed 11/256:50 pm -
1 stop5h 25m
Sun 11/2911:00 pm -
Nonstop2h 55m
Deal found 10/20![Southwest logo]()
$403
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/49:50 am -
2 stops7h 25m
Sun 12/65:20 am -
1 stop6h 05m
Deal found 10/23![Southwest logo]()
$412
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/106:34 am -
Nonstop2h 58m
Wed 11/117:29 am -
1 stop5h 47m
Deal found 10/23![United Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 10/20. 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 11/2610:40 am -
1 stop5h 40m
Sat 11/286:55 pm -
2 stops6h 20m
Deal found 10/20![Southwest logo]()
$418
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/207:15 pm -
1 stop5h 30m
Mon 11/238:30 pm -
Nonstop3h 07m
Deal found 10/23![United Airlines logo]()
$404
This Southwest deal was found by Cheapflights users on 10/20. 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.
Sat 11/216:40 pm -
1 stop5h 50m
Mon 11/309:50 am -
2 stops7h 35m
Deal found 10/20![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/278:25 pm -
1 stop4h 45m
Sat 12/56:35 am -
1 stop4h 20m
Deal found 10/24![Southwest logo]()
$424
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/215:00 pm -
Nonstop2h 50m
Sun 4/258:15 pm -
Nonstop2h 53m
Deal found 10/21![United Airlines logo]()
$475
Last-minute flights from San Antonio to ChicagoDiscover last-minute flight deals from San Antonio to Chicago. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Chicago. Data last updated October 25, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:20 pm -
1 stop28h 01m
Tue 11/36:30 am -
1 stop12h 55m
Deal found 10/21![Frontier logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/58:20 pm -
1 stop28h 01m
Mon 11/97:50 pm -
2 stops23h 35m
Deal found 10/21![Frontier logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/68:11 pm -
1 stop28h 10m
Tue 11/107:35 pm -
2 stops23h 50m
Deal found 10/22![Frontier logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/810:29 pm -
2 stops25h 52m
Thu 11/126:30 am -
1 stop12h 55m
Deal found 10/24![Frontier logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/810:29 pm -
2 stops25h 52m
Sat 11/146:30 am -
1 stop12h 55m
Deal found 10/23![Frontier logo]()
$328
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/123:35 pm -
1 stop4h 50m
Mon 11/168:50 pm -
Nonstop2h 55m
Deal found 10/21![Southwest logo]()
$323
This Mytrip deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:29 pm -
2 stops25h 18m
Mon 11/166:42 pm -
2 stops24h 43m
Deal found 10/22![Frontier logo]()
$328
This Mytrip deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1310:29 pm -
2 stops20h 01m
Mon 11/167:50 pm -
2 stops23h 35m
Deal found 10/22![Frontier logo]()
$320
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/1411:30 am -
2 stops5h 55m
Mon 11/307:20 pm -
1 stop6h 05m
Deal found 10/22![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:34 am -
Nonstop2h 59m
Fri 12/45:52 pm -
1 stop5h 12m
Deal found 10/22![United Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/2310:11 pm -
1 stop30h 59m
Mon 12/710:37 pm -
2 stops19h 24m
Deal found 10/22![Frontier logo]()
$327
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Thu 11/266:00 am -
1 stop6h 23m
Tue 12/19:20 pm -
Nonstop3h 13m
Deal found 10/20![American Airlines logo]()
$324
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 October 25, 2026.
Search for one-way flight options from San Antonio to Chicago. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Super.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/166:47 pm -
1 stop6h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Frontier logo]()
$98
This Super.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/56:47 pm -
1 stop6h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/238:22 pm -
1 stop28h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$104
This Booking.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:11 pm -
1 stop28h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Frontier logo]()
$105
This Super.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Sun 12/208:30 pm -
1 stop27h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$116
This Cheapflightsfares deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/308:28 pm -
1 stop28h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$121
This Super.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/48:20 pm -
1 stop28h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$124
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/221:54 pm -
Nonstop2h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![United Airlines logo]()
$131
This Super.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/98:20 pm -
1 stop28h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$135
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:09 am -
Nonstop2h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$136
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2312:06 pm -
1 stop7h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$136
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Sat 2/206:48 pm -
Nonstop3h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$137
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 October 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $319 (Mytrip) |
One-way from | $98 (Super.com) |
Popular in | June |
Cheapest in | February |
Average price | $419 |
Good round-trip deal | $362 or less |
Good one-way deal | $273 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 October 25, 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
Tue 12/22
1:54 pm-4:52 pm
Nonstop2h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$131
Quickest round-trip
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Thu 11/26
10:05 am-12:35 pm
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$137
San AntonioChicago
SAT San Antonio - ORD Chicago O'Hare Intl
SATORD
San Antonio
Wed 12/16
6:35 am-9:32 am
Nonstop2h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$137
San AntonioChicago
SAT San Antonio - ORD Chicago O'Hare Intl
SATORD
San Antonio
Sat 2/20
6:45 am-1:20 pm
1 stop6h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$147
San AntonioChicago
SAT San Antonio - ORD Chicago O'Hare Intl
SATORD
San Antonio
Thu 12/17
6:33 am-11:44 am
1 stop5h 11m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$147
San AntonioChicago
SAT San Antonio - ORD Chicago O'Hare Intl
SATORD
San Antonio
Sat 11/14
6:03 pm-11:26 pm
1 stop5h 23m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$147
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Tue 1/5
6:30 am-11:51 am
1 stop5h 21m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$147
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Sun 11/15
8:45 pm-1:10 am
1 stop4h 25m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Mon 11/30
5:10 pm-12:05 am
1 stop6h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$165
San AntonioChicago
SAT San Antonio - ORD Chicago O'Hare Intl
SATORD
San Antonio
Sun 12/20
6:30 pm-9:31 pm
Nonstop3h 01m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$198
Showing 1-10 of 36 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 October.
| 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 | |
| Price Accuracy1 star | 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
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
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 $344). Flying from San Antonio to Chicago in June is currently the most expensive (average of $441). 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 October 25, 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 25% versus a flight at noon.
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 October 25, 2026.
The most flights from SAT to CHI are scheduled on a Friday (28 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).
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 $348 and $498 in December.The cheapest round-trip price found within the last 5 days was $319 on Frontier (Dec 4-Dec 6).
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 51 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 October 25, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andJetBlue 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
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Comfort
8.0
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
Merrillville
Lansing
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 October 25, 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 October 25, 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 October 25, 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 October 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$114 | Average$279 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$237 | Average$394 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$287 | Average$454 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$315 | Average$482 | FlexibilityNo cancel fee | On-time63% |