$90+ 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 1/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — ORD
Nov 22 — Nov 291
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from San Jose to Illinois 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.Cheap flight deals from San Jose to Illinois
Cheapest
Best
Last-minute
One-way
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 October 23, 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 October 23, 2026.
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/175:59 pm -
2 stops18h 53m
Sun 12/207:45 am -
2 stops11h 19m
Deal found 10/21![Frontier logo]()
$316
This Delta deal was found by Cheapflights users on 10/19. 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.
Thu 11/196:30 am -
1 stop8h 35m
Thu 11/269:30 am -
1 stop9h 46m
Deal found 10/19![Delta logo]()
$317
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 12/32:00 pm -
1 stop6h 00m
Mon 12/76:05 am -
1 stop6h 20m
Deal found 10/21![Southwest logo]()
$318
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:59 pm -
1 stop9h 50m
Sat 1/25:40 am -
1 stop10h 50m
Deal found 10/22![Frontier logo]()
$318
This Southwest deal was found by Cheapflights users on 10/19. 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.
Wed 12/211:55 am -
2 stops7h 35m
Sat 12/53:00 pm -
1 stop6h 25m
Deal found 10/19![Southwest logo]()
$319
This Frontier deal was found by Cheapflights users on 10/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:41 pm -
1 stop12h 32m
Tue 11/245:15 am -
1 stop12h 15m
Deal found 10/18![Frontier logo]()
$319
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/214:15 pm -
1 stop10h 55m
Tue 11/245:15 am -
1 stop12h 15m
Deal found 10/21![Frontier logo]()
$320
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.
Mon 11/166:00 am -
Nonstop4h 10m
Wed 11/1810:10 am -
Nonstop4h 45m
Deal found 10/23![Southwest logo]()
$323
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.
Mon 12/711:55 am -
2 stops7h 35m
Thu 12/105:05 pm -
1 stop6h 55m
Deal found 10/20![Southwest logo]()
$324
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:41 pm -
1 stop12h 32m
Thu 11/265:15 am -
1 stop12h 15m
Deal found 10/21![Frontier logo]()
$324
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.
Fri 12/46:00 am -
Nonstop4h 10m
Mon 12/76:05 am -
1 stop6h 20m
Deal found 10/20![Southwest logo]()
$326
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:59 pm -
1 stop9h 50m
Wed 12/305:40 am -
1 stop10h 50m
Deal found 10/20![Frontier logo]()
$326
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 October 23, 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 October 23, 2026.
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.
Mon 11/911:00 pm -
Nonstop4h 00m
Tue 11/1010:10 am -
Nonstop4h 45m
Deal found 10/20![Southwest logo]()
$328
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/113:17 pm -
1 stop20h 37m
Tue 3/92:54 pm -
1 stop9h 39m
Deal found 10/20![Alaska Airlines logo]()
$377
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 11/161:00 pm -
1 stop8h 08m
Sun 11/2211:05 am -
2 stops11h 23m
Deal found 10/21![Delta logo]()
$384
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.
Sat 11/76:30 am -
1 stop8h 17m
Wed 11/115:30 pm -
1 stop7h 29m
Deal found 10/22![United Airlines logo]()
$449
This Southwest deal was found by Cheapflights users on 10/19. 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.
Tue 11/178:10 am -
2 stops7h 10m
Sat 11/215:55 pm -
2 stops8h 00m
Deal found 10/19![Southwest logo]()
$341
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:02 pm -
2 stops9h 01m
Wed 11/1112:25 pm -
2 stops11h 09m
Deal found 10/22![American Airlines logo]()
$729
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1810:20 am -
1 stop6h 35m
Mon 3/225:55 pm -
1 stop18h 21m
Deal found 10/22![Alaska Airlines logo]()
$397
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 11/166:20 am -
2 stops14h 48m
Sat 11/216:00 am -
2 stops11h 53m
Deal found 10/21![Delta logo]()
$399
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.
Sat 12/58:30 am -
Nonstop4h 00m
Sat 12/126:10 pm -
Nonstop4h 45m
Deal found 10/21![Southwest logo]()
$388
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:57 pm -
1 stop7h 33m
Sun 11/86:00 am -
1 stop7h 47m
Deal found 10/18![Delta logo]()
$414
This Alaska Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:11 pm -
1 stop6h 38m
Sun 11/222:16 pm -
1 stop7h 36m
Deal found 10/18![Alaska Airlines logo]()
$417
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1910:20 am -
1 stop6h 35m
Mon 3/227:55 pm -
1 stop15h 44m
Deal found 10/20![Alaska Airlines logo]()
$417
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.
Wed 2/1010:30 am -
Nonstop4h 05m
Mon 2/1510:05 am -
Nonstop4h 45m
Deal found 10/22![Southwest logo]()
$418
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1710:30 pm -
1 stop9h 56m
Wed 1/65:55 am -
1 stop8h 46m
Deal found 10/18![Delta logo]()
$424
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 11/181:40 pm -
1 stop5h 50m
Wed 11/259:45 am -
1 stop6h 25m
Deal found 10/20![Southwest logo]()
$420
This Alaska Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/203:05 pm -
1 stop6h 44m
Mon 11/237:26 am -
1 stop8h 24m
Deal found 10/18![Alaska Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:30 am -
1 stop8h 35m
Sun 11/226:23 am -
2 stops11h 16m
Deal found 10/18![Delta logo]()
$502
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.
Tue 12/16:00 am -
Nonstop4h 10m
Wed 12/23:50 pm -
Nonstop4h 40m
Deal found 10/21![Southwest logo]()
$477
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 1/274:05 pm -
1 stop27h 05m
Sat 1/308:40 am -
1 stop6h 41m
Deal found 10/21![United Airlines logo]()
$705
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:37 am -
1 stop9h 22m
Fri 11/62:07 pm -
1 stop9h 44m
Deal found 10/21![Alaska Airlines logo]()
$487
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2111:38 am -
2 stops10h 21m
Sun 11/227:30 am -
2 stops11h 46m
Deal found 10/20![Delta logo]()
$504
This American Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:00 am -
2 stops12h 21m
Tue 11/2412:14 pm -
2 stops12h 32m
Deal found 10/18![American Airlines logo]()
$769
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 11/73:05 pm -
1 stop5h 50m
Wed 11/1110:10 am -
Nonstop4h 45m
Deal found 10/20![Southwest logo]()
$485
This United Airlines deal was found by Cheapflights users on 10/19. 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 2/64:05 pm -
1 stop26h 54m
Tue 2/98:40 am -
1 stop6h 42m
Deal found 10/19![United Airlines logo]()
$740
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/187:00 am -
2 stops8h 57m
Mon 3/221:55 pm -
2 stops9h 52m
Deal found 10/20![Delta logo]()
$507
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:59 pm -
2 stops9h 41m
Tue 11/102:15 pm -
1 stop10h 16m
Deal found 10/20![Alaska Airlines logo]()
$533
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:10 am -
2 stops7h 10m
Tue 1/55:50 am -
2 stops8h 10m
Deal found 10/18![Southwest logo]()
$507
This American Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/197:15 pm -
2 stops16h 01m
Sat 1/23:50 pm -
1 stop9h 36m
Deal found 10/18![American Airlines logo]()
$830
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/203:00 pm -
1 stop7h 15m
Sun 11/229:15 pm -
Nonstop4h 40m
Deal found 10/18![Southwest logo]()
$520
This United Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/22:14 pm -
1 stop6h 44m
Fri 11/610:43 am -
1 stop27h 19m
Deal found 10/18![United Airlines logo]()
$867
Last-minute flights from San Jose to IllinoisDiscover last-minute flight deals from San Jose to Illinois. Data last updated October 23, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Illinois. Data last updated October 23, 2026 and is based on user searches.
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.
Mon 11/911:00 pm -
Nonstop4h 00m
Tue 11/1010:10 am -
Nonstop4h 45m
Deal found 10/20![Southwest logo]()
$328
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.
Mon 11/166:00 am -
Nonstop4h 10m
Wed 11/1810:10 am -
Nonstop4h 45m
Deal found 10/23![Southwest logo]()
$323
This Delta deal was found by Cheapflights users on 10/19. 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 11/161:43 pm -
1 stop6h 04m
Mon 11/232:32 pm -
1 stop9h 40m
Deal found 10/19![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 10/19. 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.
Tue 11/176:00 am -
Nonstop4h 10m
Sat 11/215:55 pm -
2 stops8h 00m
Deal found 10/19![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 10/18. 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.
Wed 11/187:40 am -
1 stop7h 25m
Tue 12/110:15 am -
2 stops8h 15m
Deal found 10/18![Southwest logo]()
$324
This Delta deal was found by Cheapflights users on 10/19. 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.
Thu 11/196:30 am -
1 stop8h 35m
Mon 11/302:32 pm -
1 stop7h 17m
Deal found 10/19![Delta logo]()
$317
This Frontier deal was found by Cheapflights users on 10/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:41 pm -
1 stop12h 32m
Tue 11/245:15 am -
1 stop12h 15m
Deal found 10/18![Frontier logo]()
$319
This Delta deal was found by Cheapflights users on 10/19. 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.
Thu 11/199:38 am -
2 stops12h 16m
Thu 11/269:30 am -
1 stop9h 46m
Deal found 10/19![Delta logo]()
$322
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:41 pm -
1 stop12h 32m
Thu 11/265:15 am -
1 stop12h 15m
Deal found 10/21![Frontier logo]()
$324
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:41 pm -
1 stop12h 32m
Mon 11/2312:05 pm -
2 stops28h 10m
Deal found 10/20![Frontier logo]()
$328
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/214:15 pm -
1 stop10h 55m
Tue 11/245:15 am -
1 stop12h 15m
Deal found 10/21![Frontier logo]()
$320
This Frontier deal was found by Cheapflights users on 10/19. 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.
Sat 11/213:10 pm -
1 stop13h 04m
Thu 11/265:15 am -
1 stop12h 15m
Deal found 10/19![Frontier logo]()
$330
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 October 23, 2026.
Search for one-way flight options from San Jose to Illinois. Find affordable one-way fares based on user searches. Data last updated October 23, 2026.
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/45:59 pm -
1 stop10h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$90
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 11/122:41 pm -
1 stop12h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$101
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/1412:58 pm -
1 stop15h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$109
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:59 pm -
1 stop9h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$115
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:52 pm -
1 stop11h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$116
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.
Mon 11/92:41 pm -
2 stops42h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Frontier logo]()
$122
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.
Mon 11/162:41 pm -
2 stops31h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Frontier logo]()
$123
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.
Mon 11/92:41 pm -
2 stops30h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Frontier logo]()
$124
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/143:48 pm -
1 stop11h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$125
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/234:15 pm -
1 stop10h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$126
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:52 pm -
2 stops15h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$133
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.
Tue 12/225:59 pm -
1 stop9h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$133
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 October 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $316 (Mytrip) |
One-way from | $90 (Priceline) |
Popular in | March |
Cheapest in | February |
Average price | $443 |
Good round-trip deal | $380 or less |
Good one-way deal | $217 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 October 23, 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
Wed 12/16
9:00 am-5:30 pm
1 stop6h 30m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$159
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Mon 12/21
4:40 pm-12:40 am
1 stop6h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$159
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Thu 11/26
6:55 am-4:50 pm
2 stops7h 55m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$165
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Fri 12/25
6:00 am-12:10 pm
Nonstop4h 10m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$167
Quickest round-trip
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Sun 11/15
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$167
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Mon 11/16
8:35 pm-5:40 am
1 stop7h 05m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$171
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Sun 11/22
7:20 pm-4:25 am
1 stop7h 05m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$177
San JoseChicago
SJC San Jose - MDW Chicago Midway
SJCMDW
San Jose
Tue 11/10
6:35 am-5:05 pm
2 stops8h 30m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$182
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Tue 11/24
9:59 am-8:03 pm
1 stop8h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$189
San JoseChicago
SJC San Jose - ORD Chicago O'Hare Intl
SJCORD
San Jose
Tue 3/16
10:20 am-6:55 pm
1 stop6h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$189
Showing 1-10 of 57 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-MDW
SJC-ORD
SJC-CMI
SJC-PIA
SJC-MLI
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-MDW
SJC-ORD
SJC-CMI
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 $573). 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 October 23, 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 $452 and $744 in December.The cheapest round-trip price found within the last 5 days was $316 on Frontier (Dec 17-Dec 20).
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 October 23, 2026.
Read through reviews of airlines operating flights from San Jose to Illinois, such as Alaska Airlines,Southwest, andDelta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Crew
8.5
Comfort
7.8
Overall
7.9
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Dec 2025
SJC - SEA
Food
7.0
Crew
8.5
Comfort
7.8
Overall
7.9
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Dec 2025
SJC - SEA
Food
7.0
Crew
8.5
Comfort
7.8
Overall
7.9
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Dec 2025
SJC - SEA
Food
7.0
Crew
8.5
Comfort
7.8
Overall
7.9
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Dec 2025
SJC - SEA
Food
7.0
Crew
8.5
Comfort
7.8
Overall
7.9
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Dec 2025
SJC - SEA
Food
7.0
Crew
8.5
Comfort
7.8
Overall
7.9
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Dec 2025
SJC - SEA
Related info for your journey
Find useful and relevant information for your journey from San Jose to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for San Jose to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from San Jose to Illinois by cabin class
Find flights from San Jose to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
San Jose and Illinois flights
Browse other San Jose and Illinois flight options. Last updated on October 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 October 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$183 | Average$490 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$200 | Average$579 | 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$514 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$278 | Average$560 | FlexibilityNo cancel fee | On-time69% |