$169+ Cheap flights from San Jose, CA (SJC) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — CHI
Sep 27 — Oct 41
Round-trip
1 adult, Economy
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Find cheap flights from San Jose 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 Jose to Chicago are usually found in February or April, booked 79 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday
Cheap flight deals from San Jose to Chicago
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Cheapest flights from San Jose to ChicagoExplore the most affordable flight options available from San Jose to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 28, 2026.
Explore the most affordable flight options available from San Jose to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 28, 2026.
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:51 pm -
1 stop7h 53m
Mon 9/287:13 pm -
2 stops17h 32m
Deal found 8/27![Delta logo]()
$295
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1911:41 am -
1 stop7h 49m
Mon 9/286:10 am -
2 stops13h 14m
Deal found 8/27![Delta logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/159:02 pm -
1 stop6h 14m
Mon 10/196:30 am -
2 stops15h 37m
Deal found 8/27![Frontier logo]()
$296
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/2011:00 pm -
Nonstop4h 00m
Thu 9/248:50 pm -
Nonstop4h 35m
Deal found 8/27![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 8/24. 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 10/308:00 am -
2 stops7h 25m
Sat 11/146:10 pm -
Nonstop4h 45m
Deal found 8/24![Southwest logo]()
$298
This Alaska Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/197:29 am -
1 stop9h 52m
Fri 9/252:18 pm -
1 stop6h 51m
Deal found 8/27![Alaska Airlines logo]()
$298
This Southwest deal was found by Cheapflights users on 8/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/510:20 am -
2 stops8h 15m
Wed 10/76:25 am -
1 stop6h 55m
Deal found 8/25![Southwest logo]()
$299
This Expedia deal was found by Cheapflights users on 8/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:29 am -
1 stop9h 52m
Thu 10/88:01 pm -
1 stop26h 20m
Deal found 8/25![Multiple Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/216:19 pm -
2 stops11h 37m
Mon 9/286:10 am -
2 stops13h 14m
Deal found 8/27![Delta logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Thu 10/82:15 pm -
2 stops14h 19m
Thu 10/158:01 pm -
1 stop26h 20m
Deal found 8/24![Frontier logo]()
$301
This Southwest deal was found by Cheapflights users on 8/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:15 pm -
1 stop5h 40m
Mon 10/57:00 am -
1 stop7h 45m
Deal found 8/25![Southwest logo]()
$302
This Expedia deal was found by Cheapflights users on 8/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:38 pm -
1 stop14h 00m
Sat 9/261:03 pm -
2 stops11h 53m
Deal found 8/25![Multiple Airlines logo]()
$302
Best flights from San Jose to ChicagoDiscover carefully curated flight deals from San Jose to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 28, 2026.
Discover carefully curated flight deals from San Jose to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 28, 2026.
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2212:51 pm -
1 stop7h 53m
Mon 9/287:13 pm -
2 stops15h 59m
Deal found 8/27![Delta logo]()
$295
This Alaska Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Sun 10/253:51 pm -
1 stop19h 34m
Thu 10/297:49 pm -
1 stop16h 05m
Deal found 8/27![Alaska Airlines logo]()
$298
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/106:30 am -
2 stops9h 30m
Sat 10/176:15 am -
1 stop6h 10m
Deal found 8/26![Southwest logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Thu 11/122:41 pm -
2 stops17h 52m
Sun 11/158:37 pm -
1 stop19h 09m
Deal found 8/24![Multiple Airlines logo]()
$306
This United Airlines deal was found by Cheapflights users on 8/22. 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.
Sun 10/46:30 am -
Nonstop4h 22m
Wed 10/77:55 pm -
Nonstop4h 47m
Deal found 8/22![United Airlines logo]()
$328
This Southwest deal was found by Cheapflights users on 8/22. 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 11/68:30 pm -
1 stop7h 25m
Mon 11/95:20 pm -
2 stops7h 10m
Deal found 8/22![Southwest logo]()
$312
This United Airlines deal was found by Cheapflights users on 8/23. 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 10/62:08 pm -
Nonstop4h 27m
Tue 10/207:55 pm -
Nonstop4h 47m
Deal found 8/23![United Airlines logo]()
$337
This Alaska Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Sun 10/118:06 pm -
1 stop15h 19m
Sun 10/187:49 pm -
1 stop16h 05m
Deal found 8/27![Alaska Airlines logo]()
$337
This KAYAK deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Wed 12/97:00 am -
1 stop8h 31m
Fri 12/1111:35 am -
1 stop9h 37m
Deal found 8/27![Delta logo]()
$356
This Southwest deal was found by Cheapflights users on 8/24. 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.
Sat 10/36:45 pm -
1 stop7h 45m
Tue 10/61:05 pm -
2 stops7h 55m
Deal found 8/24![Southwest logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/152:15 pm -
2 stops19h 12m
Sun 10/189:33 pm -
1 stop17h 47m
Deal found 8/26![Multiple Airlines logo]()
$368
This United Airlines deal was found by Cheapflights users on 8/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/38:45 am -
1 stop7h 45m
Tue 10/67:55 pm -
Nonstop4h 47m
Deal found 8/24![United Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 8/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:25 am -
1 stop8h 36m
Sun 9/277:07 am -
1 stop9h 07m
Deal found 8/23![Delta logo]()
$357
This Alaska Airlines deal was found by Cheapflights users on 8/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/223:05 pm -
1 stop6h 44m
Sat 11/287:26 am -
1 stop8h 24m
Deal found 8/23![Alaska Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 8/22. 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.
Thu 12/1711:00 pm -
Nonstop4h 00m
Wed 12/306:00 am -
2 stops8h 05m
Deal found 8/22![Southwest logo]()
$362
This United Airlines deal was found by Cheapflights users on 8/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:45 am -
1 stop9h 07m
Tue 10/67:55 pm -
Nonstop4h 47m
Deal found 8/25![United Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 8/22. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/233:05 pm -
1 stop6h 44m
Mon 11/307:26 am -
1 stop8h 24m
Deal found 8/22![Alaska Airlines logo]()
$402
This Southwest deal was found by Cheapflights users on 8/22. 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.
Thu 10/2210:20 am -
2 stops8h 15m
Sun 10/255:10 am -
1 stop8h 15m
Deal found 8/22![Southwest logo]()
$384
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 12/92:09 pm -
Nonstop4h 19m
Fri 12/119:07 am -
Nonstop4h 52m
Deal found 8/27![United Airlines logo]()
$391
This Southwest deal was found by Cheapflights users on 8/22. 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 11/68:45 am -
1 stop7h 10m
Sun 11/87:30 am -
1 stop8h 25m
Deal found 8/22![Southwest logo]()
$392
This United Airlines deal was found by Cheapflights users on 8/22. 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.
Thu 10/110:45 am -
1 stop9h 07m
Mon 10/57:55 pm -
Nonstop4h 47m
Deal found 8/22![United Airlines logo]()
$410
This Southwest deal was found by Cheapflights users on 8/23. 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.
Tue 9/811:00 pm -
Nonstop4h 00m
Thu 9/246:15 am -
1 stop6h 15m
Deal found 8/23![Southwest logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1911:58 am -
1 stop21h 39m
Thu 12/2412:27 pm -
1 stop24h 36m
Deal found 8/26![Multiple Airlines logo]()
$669
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/229:55 am -
Nonstop4h 05m
Sun 9/2710:10 am -
Nonstop4h 25m
Deal found 8/26![Southwest logo]()
$432
This Southwest deal was found by Cheapflights users on 8/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:15 pm -
1 stop6h 55m
Mon 9/216:15 am -
1 stop7h 40m
Deal found 8/25![Southwest logo]()
$433
Last-minute flights from San Jose to ChicagoDiscover last-minute flight deals from San Jose to Chicago. Data last updated August 28, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Chicago. Data last updated August 28, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 8/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:14 pm -
1 stop7h 45m
Tue 9/157:20 am -
1 stop8h 10m
Deal found 8/22![Multiple Airlines logo]()
$334
This Expedia deal was found by Cheapflights users on 8/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:14 pm -
1 stop7h 45m
Mon 9/148:17 pm -
1 stop15h 06m
Deal found 8/24![Multiple Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:51 pm -
1 stop7h 53m
Mon 9/287:13 pm -
2 stops17h 32m
Deal found 8/27![Delta logo]()
$295
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/2011:00 pm -
Nonstop4h 00m
Thu 9/248:50 pm -
Nonstop4h 35m
Deal found 8/27![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 8/23. 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.
Sun 9/209:05 pm -
1 stop6h 50m
Tue 9/296:50 am -
2 stops8h 00m
Deal found 8/23![Southwest logo]()
$312
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/203:20 pm -
1 stop7h 10m
Sat 9/261:50 pm -
1 stop6h 15m
Deal found 8/27![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 8/24. 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.
Tue 9/2212:51 pm -
1 stop7h 53m
Sat 9/269:59 am -
1 stop9h 47m
Deal found 8/24![Delta logo]()
$308
This Delta deal was found by Cheapflights users on 8/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2211:41 am -
2 stops19h 26m
Tue 9/295:11 pm -
2 stops19h 34m
Deal found 8/22![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 8/24. 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.
Wed 9/238:00 am -
2 stops7h 10m
Wed 9/238:30 pm -
Nonstop4h 35m
Deal found 8/24![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 8/24. 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.
Thu 9/247:35 pm -
1 stop7h 30m
Sat 9/262:15 pm -
2 stops9h 05m
Deal found 8/24![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates ” 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 9/2411:00 pm -
Nonstop4h 00m
Thu 10/19:15 pm -
Nonstop4h 35m
Deal found 8/27![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 8/24. 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 9/2511:00 pm -
Nonstop4h 00m
Tue 9/296:50 am -
2 stops8h 00m
Deal found 8/24![Southwest logo]()
$302
One-way flights from San Jose to ChicagoSearch for one-way flight options from San Jose to Chicago. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
Search for one-way flight options from San Jose to Chicago. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
This Southwest deal was found by Cheapflights users on 8/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:00 pm -
Nonstop4h 00m
Deal found 8/25![Southwest logo]()
$169
This United Airlines deal was found by Cheapflights users on 8/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/162:10 pm -
Nonstop4h 25m
Deal found 8/25![United Airlines logo]()
$169
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/83:10 pm -
1 stop7h 05m
Deal found 8/26![Southwest logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/141:38 pm -
1 stop14h 00m
Deal found 8/25![Frontier logo]()
$170
This Delta deal was found by Cheapflights users on 8/24. 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.
Tue 9/228:41 pm -
2 stops19h 38m
Deal found 8/24![Delta logo]()
$173
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/1911:41 am -
2 stops19h 44m
Deal found 8/26![Delta logo]()
$173
This Alaska Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Sun 11/226:56 pm -
1 stop16h 22m
Deal found 8/27![Alaska Airlines logo]()
$174
This Southwest deal was found by Cheapflights users on 8/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:00 am -
2 stops9h 25m
Deal found 8/25![Southwest logo]()
$175
This Southwest deal was found by Cheapflights users on 8/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:55 pm -
1 stop6h 45m
Deal found 8/25![Southwest logo]()
$179
This American Airlines deal was found by Cheapflights users on 8/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:48 pm -
1 stop7h 26m
Deal found 8/25![American Airlines logo]()
$179
This Delta deal was found by Cheapflights users on 8/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1612:51 pm -
1 stop7h 53m
Deal found 8/25![Delta logo]()
$180
This CheapOair deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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.
Mon 11/302:03 pm -
1 stop19h 43m
Deal found 8/26![Frontier logo]()
$180
Find flight deals from San Jose to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) 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 August 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $295 (Delta) |
One-way from | $169 (Southwest) |
Popular in | March |
Cheapest in | February |
Average price | $428 |
Good round-trip deal | $387 or less |
Good one-way deal | $175 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Jose 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 August 28, 2026.
Use the filters below to find and compare flights from San Jose to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Tue 9/22
12:51 pm-10:44 pm
1 stop7h 53m
Chicago Midway
Mon 9/28
7:13 pm-9:12 am
2 stops15h 59m
$295
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Sun 10/25
3:51 pm-1:25 pm
1 stop19h 34m
Chicago O'Hare Intl
Thu 10/29
7:49 pm-9:54 am
1 stop16h 05m
$298
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Sat 10/10
6:30 am-6:00 pm
2 stops9h 30m
Chicago Midway
Sat 10/17
6:15 am-10:25 am
1 stop6h 10m
$303
San JoseChicago
SJC San Jose - RFD Chicago Greater Rockford
SJCRFD
San Jose
Thu 11/12
2:41 pm-10:33 am
2 stops17h 52m
Chicago Greater Rockford
Sun 11/15
8:37 pm-1:46 pm
1 stop19h 09m
$306
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Fri 11/6
8:30 pm-5:55 am
1 stop7h 25m
Chicago Midway
Mon 11/9
5:20 pm-10:30 pm
2 stops7h 10m
$312
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Sun 10/4
6:30 am-12:52 pm
Nonstop4h 22m
Chicago O'Hare Intl
Wed 10/7
7:55 pm-10:42 pm
Nonstop4h 47m
$328
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Sat 10/3
6:45 pm-4:30 am
1 stop7h 45m
Chicago Midway
Tue 10/6
1:05 pm-7:00 pm
2 stops7h 55m
$328
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Tue 10/6
2:08 pm-8:35 pm
Nonstop4h 27m
Chicago O'Hare Intl
Tue 10/20
7:55 pm-10:42 pm
Nonstop4h 47m
$337
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Sun 10/11
8:06 pm-1:25 pm
1 stop15h 19m
Chicago O'Hare Intl
Sun 10/18
7:49 pm-9:54 am
1 stop16h 05m
$337
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Sat 10/3
8:45 am-6:30 pm
1 stop7h 45m
Chicago O'Hare Intl
Tue 10/6
7:55 pm-10:42 pm
Nonstop4h 47m
$347
Showing 1-10 of 54 resultsSorted by cheapest first
Compare providers for flights from San Jose 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 Jose to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San Jose, California-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Jose, California-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Jose, California-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Jose, California-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 Jose, California-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 Jose to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San Jose with our price prediction graph.
SJC-CHI
SJC-ORD
SJC-MDW
SJC-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 Jose to Chicago
SJC-CHI
SJC-ORD
SJC-MDW
SJC-RFD
What is the cheapest month to book a flight from San Jose, California to Chicago?
Currently, April is the cheapest month in which you can book a flight from San Jose, California to Chicago (average of $405). Flying from San Jose, California to Chicago in June is currently the most expensive (average of $577). 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 SJC to CHI?
Find hourly flight availability from San Jose 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 August 28, 2026.
A simple way to save on the total cost of your ticket is to fly from San Jose, California to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 22% on your trip compared to booking a flight at noon.
Weekly flight availability from San Jose, California to Chicago
Explore weekly flight availability from San Jose 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 August 28, 2026.
The most flights from SJC to CHI are scheduled on a Tuesday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).
How much does it cost to fly round-trip from San Jose, California to Chicago?
Airfare is below average for this route at the moment.
San Jose, California to Chicago flights typically cost between $359 and $518 in September.The cheapest round-trip price found within the last 5 days was $295 on Delta (Sep 19-Sep 28).
How far ahead should I book a flight from San Jose, California to Chicago?
The best time to book flights from San Jose, California to Chicago is 53 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
The best insider tips for San Jose 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 Jose 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 August 28, 2026.
Peruse reviews from past customers who have flown with Southwest,Alaska Airlines, andDelta from San Jose to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
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 Jose 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?
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San Jose and Chicago flights
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Top 6 airlines flying from San Jose to Chicago
Discover the top 6 airlines that operate flights from San Jose 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 August 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$131 | Average$490 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$200 | Average$427 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$236 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$256 | Average$346 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$256 | Average$517 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$294 | Average$558 | FlexibilityNo cancel fee | On-time69% |