$170+ Cheap flights from San Jose, CA (SJC) to Illinois
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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — ORD
Oct 24 — Oct 311
Round-trip
1 adult, Economy
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Find cheap flights from San Jose to Illinois with Cheapflights
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Cheapest flights from San Jose to IllinoisExplore the most affordable flight options available from San Jose to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 24, 2026.
Explore the most affordable flight options available from San Jose to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 24, 2026.
This Mytrip deal was found by Cheapflights users on 9/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/59:07 pm -
2 stops25h 14m
Mon 11/96:30 am -
2 stops15h 42m
Deal found 9/19![Frontier logo]()
$302
This Priceline deal was found by Cheapflights users on 9/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:02 pm -
1 stop6h 14m
Mon 10/267:20 am -
1 stop9h 35m
Deal found 9/21![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:41 pm -
1 stop12h 32m
Mon 11/26:30 am -
2 stops15h 42m
Deal found 9/20![Frontier logo]()
$306
This Expedia deal was found by Cheapflights users on 9/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:37 am -
1 stop9h 22m
Thu 11/195:15 pm -
1 stop24h 15m
Deal found 9/19![Multiple Airlines logo]()
$307
This CheapOair deal was found by Cheapflights users on 9/19. 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 11/192:41 pm -
1 stop12h 32m
Sun 11/2210:30 pm -
1 stop17h 45m
Deal found 9/19![Frontier logo]()
$308
This Orbitz deal was found by Cheapflights users on 9/22. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:02 pm -
1 stop6h 14m
Mon 10/197:49 pm -
1 stop16h 05m
Deal found 9/22![Multiple Airlines logo]()
$309
This Mytrip deal was found by Cheapflights users on 9/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:07 pm -
2 stops25h 14m
Thu 11/196:30 am -
2 stops15h 42m
Deal found 9/20![Frontier logo]()
$311
This Mytrip deal was found by Cheapflights users on 9/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/199:02 pm -
2 stops25h 22m
Mon 10/266:30 am -
2 stops15h 37m
Deal found 9/20![Frontier logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Fri 10/99:02 pm -
2 stops31h 32m
Wed 10/148:01 pm -
1 stop26h 06m
Deal found 9/19![Frontier logo]()
$314
This Alaska Airlines deal was found by Cheapflights users on 9/23. 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.
Fri 10/306:17 am -
1 stop10h 03m
Mon 11/27:57 pm -
1 stop15h 24m
Deal found 9/23![Alaska Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 9/22. 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.
Sun 10/252:15 pm -
1 stop14h 19m
Wed 10/286:30 am -
2 stops39h 42m
Deal found 9/22![Frontier logo]()
$316
This Delta deal was found by Cheapflights users on 9/23. 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.
Mon 11/26:45 am -
2 stops24h 47m
Mon 11/91:31 pm -
2 stops21h 27m
Deal found 9/23![Delta logo]()
$333
Best flights from San Jose to IllinoisDiscover carefully curated flight deals from San Jose to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 24, 2026.
Discover carefully curated flight deals from San Jose to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 24, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/21. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2511:12 am -
1 stop10h 47m
Thu 10/297:20 am -
1 stop9h 35m
Deal found 9/21![Alaska Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 9/18. 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.
Sat 10/1711:00 pm -
Nonstop4h 00m
Mon 10/199:15 pm -
Nonstop4h 40m
Deal found 9/18![Southwest logo]()
$343
This Delta deal was found by Cheapflights users on 9/21. 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.
Tue 10/2712:57 pm -
1 stop7h 36m
Sat 10/3110:12 am -
2 stops8h 08m
Deal found 9/21![Delta logo]()
$362
This American Airlines deal was found by Cheapflights users on 9/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/132:41 pm -
1 stop6h 36m
Sat 10/174:38 pm -
1 stop7h 30m
Deal found 9/22![American Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 9/23. 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 11/122:14 pm -
Nonstop4h 18m
Sun 11/159:02 am -
Nonstop5h 00m
Deal found 9/23![United Airlines logo]()
$397
This Southwest deal was found by Cheapflights users on 9/21. 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 11/511:00 pm -
Nonstop4h 00m
Thu 11/127:30 am -
1 stop8h 25m
Deal found 9/21![Southwest logo]()
$343
This Delta deal was found by Cheapflights users on 9/21. 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.
Tue 10/271:40 pm -
1 stop6h 25m
Sat 10/3112:30 pm -
2 stops7h 50m
Deal found 9/21![Delta logo]()
$362
This Southwest deal was found by Cheapflights users on 9/22. 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.
Mon 10/266:00 am -
Nonstop4h 00m
Wed 10/286:30 am -
1 stop8h 05m
Deal found 9/22![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 9/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:32 pm -
2 stops10h 21m
Wed 10/286:20 am -
2 stops9h 37m
Deal found 9/19![Delta logo]()
$368
This United Airlines deal was found by Cheapflights users on 9/21. 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.
Tue 10/62:08 pm -
1 stop6h 50m
Sat 10/103:41 pm -
1 stop9h 01m
Deal found 9/21![United Airlines logo]()
$449
This Delta deal was found by Cheapflights users on 9/21. 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.
Fri 10/168:32 pm -
2 stops10h 21m
Wed 10/217:20 am -
1 stop16h 48m
Deal found 9/21![Delta logo]()
$381
This Southwest deal was found by Cheapflights users on 9/19. 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.
Fri 11/1311:00 pm -
Nonstop4h 00m
Thu 11/195:50 am -
1 stop7h 20m
Deal found 9/19![Southwest logo]()
$383
This United Airlines deal was found by Cheapflights users on 9/20. 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 10/191:00 pm -
1 stop6h 52m
Mon 10/268:08 pm -
Nonstop4h 51m
Deal found 9/20![United Airlines logo]()
$450
This American Airlines deal was found by Cheapflights users on 9/20. 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.
Sun 11/2211:56 am -
1 stop8h 06m
Wed 12/167:11 am -
1 stop8h 49m
Deal found 9/20![American Airlines logo]()
$540
This United Airlines deal was found by Cheapflights users on 9/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:30 am -
Nonstop4h 22m
Mon 10/268:08 pm -
Nonstop4h 51m
Deal found 9/19![United Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 9/23. 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.
Sun 10/257:33 pm -
2 stops10h 08m
Thu 10/296:20 am -
2 stops9h 37m
Deal found 9/23![Delta logo]()
$428
This Southwest deal was found by Cheapflights users on 9/19. 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.
Fri 10/233:10 pm -
1 stop7h 05m
Sun 10/255:10 am -
1 stop8h 15m
Deal found 9/19![Southwest logo]()
$448
This United Airlines deal was found by Cheapflights users on 9/23. 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.
Wed 10/286:30 am -
Nonstop4h 24m
Sat 10/319:02 am -
Nonstop5h 00m
Deal found 9/23![United Airlines logo]()
$457
This American Airlines deal was found by Cheapflights users on 9/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
2 stops14h 03m
Sat 12/1212:13 pm -
2 stops11h 21m
Deal found 9/19![American Airlines logo]()
$564
This United Airlines deal was found by Cheapflights users on 9/21. 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.
Mon 11/96:30 am -
Nonstop4h 24m
Thu 11/129:02 am -
Nonstop5h 00m
Deal found 9/21![United Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 9/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:20 am -
1 stop8h 27m
Sun 11/19:29 am -
2 stops10h 09m
Deal found 9/20![Delta logo]()
$463
This United Airlines deal was found by Cheapflights users on 9/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:45 am -
1 stop9h 07m
Mon 10/268:08 pm -
Nonstop4h 51m
Deal found 9/19![United Airlines logo]()
$467
This United Airlines deal was found by Cheapflights users on 9/21. 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.
Tue 10/276:30 am -
Nonstop4h 24m
Sat 10/318:40 am -
1 stop6h 38m
Deal found 9/21![United Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 9/21. 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.
Tue 10/136:34 pm -
2 stops13h 44m
Sat 10/1711:08 am -
2 stops10h 44m
Deal found 9/21![Delta logo]()
$518
This American Airlines deal was found by Cheapflights users on 9/21. 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 10/66:00 am -
2 stops10h 05m
Sat 10/102:37 pm -
1 stop9h 31m
Deal found 9/21![American Airlines logo]()
$722
This United Airlines deal was found by Cheapflights users on 9/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:30 am -
1 stop6h 36m
Sat 10/318:41 am -
1 stop6h 37m
Deal found 9/19![United Airlines logo]()
$499
This American Airlines deal was found by Cheapflights users on 9/21. 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.
Mon 11/307:26 pm -
2 stops14h 12m
Thu 12/177:11 am -
1 stop8h 52m
Deal found 9/21![American Airlines logo]()
$742
This American Airlines deal was found by Cheapflights users on 9/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
2 stops8h 59m
Mon 10/264:42 pm -
1 stop7h 26m
Deal found 9/23![American Airlines logo]()
$757
This United Airlines deal was found by Cheapflights users on 9/23. 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.
Wed 1/271:04 pm -
1 stop5h 43m
Sat 1/308:50 am -
1 stop6h 36m
Deal found 9/23![United Airlines logo]()
$579
This American Airlines deal was found by Cheapflights users on 9/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:00 am -
2 stops10h 05m
Mon 10/267:03 pm -
2 stops25h 33m
Deal found 9/24![American Airlines logo]()
$779
Last-minute flights from San Jose to IllinoisDiscover last-minute flight deals from San Jose to Illinois. Data last updated September 24, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Illinois. Data last updated September 24, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Fri 10/99:02 pm -
2 stops31h 32m
Wed 10/148:01 pm -
1 stop26h 06m
Deal found 9/19![Frontier logo]()
$314
This Orbitz deal was found by Cheapflights users on 9/22. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:02 pm -
1 stop6h 14m
Mon 10/197:49 pm -
1 stop16h 05m
Deal found 9/22![Multiple Airlines logo]()
$309
This Orbitz deal was found by Cheapflights users on 9/24. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:02 am -
1 stop8h 18m
Sun 10/253:30 pm -
1 stop23h 50m
Deal found 9/24![Multiple Airlines logo]()
$323
This Mytrip deal was found by Cheapflights users on 9/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/199:02 pm -
2 stops25h 22m
Mon 10/266:30 am -
2 stops15h 37m
Deal found 9/20![Frontier logo]()
$312
This Priceline deal was found by Cheapflights users on 9/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:02 pm -
1 stop6h 14m
Mon 10/267:20 am -
1 stop9h 35m
Deal found 9/21![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 10/232:15 pm -
1 stop14h 19m
Wed 10/286:30 am -
2 stops39h 42m
Deal found 9/22![Frontier logo]()
$319
This Expedia deal was found by Cheapflights users on 9/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:02 pm -
1 stop6h 14m
Sun 10/253:30 pm -
1 stop23h 50m
Deal found 9/22![Frontier logo]()
$324
This Travelocity deal was found by Cheapflights users on 9/22. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/252:15 pm -
1 stop14h 19m
Wed 10/287:00 am -
1 stop9h 18m
Deal found 9/22![Multiple Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 9/22. 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.
Sun 10/252:15 pm -
1 stop14h 19m
Wed 10/286:30 am -
2 stops39h 42m
Deal found 9/22![Frontier logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Sun 10/252:15 pm -
1 stop14h 19m
Thu 11/56:30 am -
2 stops15h 42m
Deal found 9/19![Frontier logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:41 pm -
1 stop12h 32m
Mon 11/26:30 am -
2 stops15h 42m
Deal found 9/20![Frontier logo]()
$306
This Alaska Airlines deal was found by Cheapflights users on 9/23. 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.
Fri 10/306:17 am -
1 stop10h 03m
Mon 11/27:57 pm -
1 stop15h 24m
Deal found 9/23![Alaska Airlines logo]()
$315
One-way flights from San Jose to IllinoisSearch for one-way flight options from San Jose to Illinois. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
Search for one-way flight options from San Jose to Illinois. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/162:41 pm -
2 stops18h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:02 pm -
2 stops15h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$171
This Super.com deal was found by Cheapflights users on 9/19. 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.
Sun 11/82:41 pm -
1 stop12h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$172
This Delta deal was found by Cheapflights users on 9/21. 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.
Tue 10/208:32 pm -
2 stops18h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$173
This Delta deal was found by Cheapflights users on 9/22. 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.
Mon 11/211:41 am -
2 stops19h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Delta logo]()
$173
This Southwest deal was found by Cheapflights users on 9/22. 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.
Wed 10/1411:00 pm -
Nonstop4h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$175
This Frontier deal was found by Cheapflights users on 9/19. 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.
Sun 11/224:15 pm -
1 stop10h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 9/21. 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.
Mon 10/199:02 pm -
2 stops15h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$176
This Southwest deal was found by Cheapflights users on 9/23. 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.
Wed 10/218:30 pm -
1 stop7h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Southwest logo]()
$179
This Delta deal was found by Cheapflights users on 9/21. 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.
Wed 10/1411:30 am -
1 stop10h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:15 pm -
2 stops31h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$181
This Expedia deal was found by Cheapflights users on 9/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/152:15 pm -
1 stop14h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$183
Find flight deals from San Jose to Illinois
Keep the following information in mind while searching for San Jose to Illinois flight deals. Data was last updated September 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $302 (Mytrip) |
One-way from | $170 (Kiwi.com) |
Popular in | March |
Cheapest in | February |
Average price | $453 |
Good round-trip deal | $387 or less |
Good one-way deal | $236 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Jose to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 24, 2026.
Use the filters below to find and compare flights from San Jose to Illinois 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 11/17
11:38 am-9:46 am
2 stops20h 08m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$173
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Wed 11/18
6:30 am-2:15 pm
1 stop5h 45m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Wed 12/16
6:20 am-4:50 pm
1 stop8h 30m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Wed 11/11
1:40 pm-9:30 pm
1 stop5h 50m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Wed 10/21
6:30 am-4:14 pm
1 stop7h 44m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Thu 10/15
4:50 pm-1:15 am
1 stop6h 25m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Sat 10/17
6:45 pm-4:30 am
1 stop7h 45m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Thu 10/29
6:30 am-4:14 pm
1 stop7h 44m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Wed 11/18
9:38 am-10:54 pm
2 stops11h 16m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$184
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Wed 11/18
7:00 am-9:33 pm
2 stops12h 33m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$184
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from San Jose to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from San Jose with our price prediction graph.
SJC-ORD
SJC-MDW
SJC-MLI
SJC-PIA
SJC-CMI
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 Illinois
SJC-USIL
SJC-ORD
SJC-MDW
SJC-MLI
SJC-PIA
What is the cheapest month to book a flight from San Jose, California to Illinois?
Currently, April is the cheapest month in which you can book a flight from San Jose, California to Illinois (average of $405). Flying from San Jose, California to Illinois 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 IL?
Find hourly flight availability from San Jose to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 24, 2026.
It’s optimal to fly from San Jose, California to Illinois in the afternoon. By choosing this option you can save up to 22% on the cost of your flight, compared to a flight at noon.
How much does it cost to fly round-trip from San Jose, California to Illinois?
Airfare is below average for this route at the moment.
San Jose, California to Illinois flights typically cost between $362 and $575 in November.The cheapest round-trip price found within the last 5 days was $302 on Frontier (Nov 5-Nov 9).
How far ahead should I book a flight from San Jose, California to Illinois?
The price you pay for your flight from San Jose, California to Illinois may vary depending on when you book. For the best chance of a lower fare, look to book 53 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated September 24, 2026.
Read through reviews of airlines operating flights from San Jose to Illinois, such as Southwest,Alaska Airlines, andDelta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
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Complete your trip
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San Jose and Illinois flights
Browse other San Jose and Illinois flight options. Last updated on September 24, 2026.
Popular flight searches
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San Jose to Illinois flights
Consider these flights traveling from San Jose to Illinois.
Top 6 airlines flying from San Jose to Illinois
Discover the top 6 airlines that operate flights from San Jose to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$131 | Average$490 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$236 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$256 | Average$339 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$256 | Average$514 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$278 | Average$547 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$438 | Average$718 | FlexibilityNo cancel fee | On-time71% |