$145+ Cheap flights from San Jose, CA (SJC) to Illinois
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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — ORD
juin 30 — juil. 71
Round-trip
1 adult, Economy
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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 mai 31, 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 mai 31, 2026.
This Southwest deal was found by Cheapflights users on 5/26. 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.
mar. 7/710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
mar. 7/148:55 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 5/26![Southwest logo]()
$298
This Travelocity deal was found by Cheapflights users on 5/26. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/233:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
mar. 6/306:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/26![Alaska Airlines logo]()
$303
This Expedia deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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.
sam. 7/48:25 pm
SJC
- ORD
1 stop7h 54m
Multiple Airlines
mar. 7/76:20 am
ORD
- SJC
1 stop7h 04m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$306
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
sam. 9/1211:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
mar. 9/158:30 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 5/29![Southwest logo]()
$308
This United Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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.
lun. 8/312:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
mar. 9/18:59 am
ORD
- SJC
Nonstop4h 46m
United Airlines
Deal found 5/28![United Airlines logo]()
$308
This Alaska Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
jeu. 8/272:25 pm
SJC
- ORD
1 stop7h 34m
Alaska Airlines
jeu. 9/36:01 am
ORD
- SJC
1 stop9h 44m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$309
This Alaska Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
mar. 6/302:19 pm
SJC
- ORD
1 stop12h 41m
Alaska Airlines
sam. 7/46:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/29![Alaska Airlines logo]()
$310
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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.
ven. 9/1811:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
mar. 9/228:30 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 5/28![Southwest logo]()
$311
This Expedia deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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.
dim. 7/58:23 pm
SJC
- ORD
1 stop7h 54m
Multiple Airlines
mer. 7/86:20 am
ORD
- SJC
1 stop7h 04m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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.
mar. 11/106:00 am
SJC
- MDW
Nonstop4h 10m
Southwest
mar. 11/101:25 pm
MDW
- SJC
2 stops8h 25m
Southwest
Deal found 5/28![Southwest logo]()
$313
This Alaska Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
mar. 7/73:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
mer. 7/156:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/31![Alaska Airlines logo]()
$313
This Delta deal was found by Cheapflights users on 5/26. 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.
lun. 7/134:30 pm
SJC
- ORD
2 stops14h 00m
Delta
mer. 7/297:37 am
ORD
- SJC
1 stop8h 35m
Delta
Deal found 5/26![Delta logo]()
$315
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 mai 31, 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 mai 31, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
mer. 7/296:37 pm
SJC
- ORD
1 stop8h 23m
Alaska Airlines
mar. 8/116:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$318
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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.
mar. 7/141:30 pm
SJC
- MDW
1 stop7h 40m
Southwest
mar. 7/215:25 am
MDW
- SJC
2 stops8h 00m
Southwest
Deal found 5/28![Southwest logo]()
$323
This United Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
jeu. 9/172:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
mar. 9/228:59 am
ORD
- SJC
Nonstop4h 46m
United Airlines
Deal found 5/30![United Airlines logo]()
$338
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
ven. 9/412:37 pm
SJC
- MLI
1 stop7h 51m
Delta
mer. 9/95:00 pm
MLI
- SJC
1 stop7h 41m
Delta
Deal found 5/29![Delta logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 5/26. 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.
jeu. 9/109:10 am
SJC
- RFD
1 stop9h 29m
Multiple Airlines
dim. 9/139:29 pm
RFD
- SJC
2 stops24h 39m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$417
This Kiwi.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
lun. 7/132:12 pm
SJC
- STL
1 stop25h 53m
Frontier
mar. 7/218:08 pm
STL
- SJC
2 stops43h 09m
Frontier
Deal found 5/30![Frontier logo]()
$498
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
sam. 7/182:23 pm
SJC
- EVV
1 stop7h 08m
American Airlines
lun. 7/275:19 am
EVV
- SJC
1 stop7h 30m
American Airlines
Deal found 5/29![American Airlines logo]()
$520
This Southwest deal was found by Cheapflights users on 5/26. 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.
mar. 9/228:15 pm
SJC
- MDW
1 stop6h 15m
Southwest
jeu. 9/246:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Deal found 5/26![Southwest logo]()
$345
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
ven. 9/410:10 pm
SJC
- MLI
1 stop10h 15m
Delta
jeu. 9/105:00 pm
MLI
- SJC
1 stop7h 41m
Delta
Deal found 5/29![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
sam. 9/52:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
mar. 9/88:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 5/31![United Airlines logo]()
$365
This Delta deal was found by Cheapflights users on 5/27. 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.
jeu. 9/246:59 am
SJC
- BMI
2 stops13h 25m
Delta
lun. 9/2812:08 pm
BMI
- SJC
2 stops12h 05m
Delta
Deal found 5/27![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 5/26. 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.
lun. 6/221:50 pm
SJC
- MDW
1 stop7h 35m
Southwest
mer. 6/245:30 am
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 5/26![Southwest logo]()
$370
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
jeu. 9/105:45 am
SJC
- MDW
2 stops10h 20m
Delta
dim. 9/1310:35 am
MDW
- SJC
1 stop10h 02m
Delta
Deal found 5/29![Delta logo]()
$363
This Southwest deal was found by Cheapflights users on 5/26. 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.
ven. 7/1010:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
mer. 7/158:55 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 5/26![Southwest logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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.
jeu. 7/238:23 pm
SJC
- RFD
2 stops37h 45m
Multiple Airlines
dim. 8/21:14 pm
RFD
- SJC
1 stop26h 03m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$454
This Alaska Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
sam. 7/48:00 am
SJC
- STL
1 stop6h 37m
Alaska Airlines
mer. 7/85:37 pm
STL
- SJC
1 stop7h 44m
Alaska Airlines
Deal found 5/29![Alaska Airlines logo]()
$477
This United Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
mar. 7/146:30 am
SJC
- ORD
Nonstop4h 24m
United Airlines
mar. 7/217:58 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Deal found 5/31![United Airlines logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
jeu. 9/249:10 am
SJC
- RFD
1 stop9h 29m
Multiple Airlines
dim. 9/279:29 pm
RFD
- SJC
1 stop18h 00m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$461
This Delta deal was found by Cheapflights users on 5/26. 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.
mer. 6/1012:46 pm
SJC
- MLI
1 stop7h 48m
Delta
mer. 6/245:17 pm
MLI
- SJC
1 stop7h 40m
Delta
Deal found 5/26![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 5/27. 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.
mer. 6/2410:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
mer. 7/16:55 pm
MDW
- SJC
1 stop6h 30m
Southwest
Deal found 5/27![Southwest logo]()
$395
This United Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
mar. 8/116:20 am
SJC
- STL
1 stop7h 18m
United Airlines
mar. 8/184:40 pm
STL
- SJC
1 stop6h 17m
United Airlines
Deal found 5/31![United Airlines logo]()
$440
This Alaska Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
sam. 7/256:47 pm
SJC
- ORD
1 stop8h 13m
Alaska Airlines
dim. 7/267:20 am
ORD
- SJC
1 stop8h 03m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$506
This Delta deal was found by Cheapflights users on 5/27. 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.
mar. 6/1612:46 pm
SJC
- MLI
1 stop7h 48m
Delta
mer. 6/245:17 pm
MLI
- SJC
1 stop7h 40m
Delta
Deal found 5/27![Delta logo]()
$384
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
mer. 7/811:47 am
SJC
- CMI
1 stop8h 12m
American Airlines
mer. 7/1511:37 am
CMI
- SJC
2 stops13h 04m
American Airlines
Deal found 5/29![American Airlines logo]()
$567
This Kiwi.com deal was found by Cheapflights users on 5/26. 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.
jeu. 9/179:10 am
SJC
- RFD
1 stop9h 29m
Multiple Airlines
dim. 9/209:29 pm
RFD
- SJC
1 stop18h 00m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$478
This United Airlines deal was found by Cheapflights users on 5/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/1112:51 pm
SJC
- ORD
1 stop9h 08m
United Airlines
sam. 8/158:59 am
ORD
- SJC
Nonstop4h 46m
United Airlines
Deal found 5/26![United Airlines logo]()
$440
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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.
lun. 7/204:20 pm
SJC
- MDW
1 stop6h 00m
Southwest
ven. 7/248:50 pm
MDW
- SJC
Nonstop4h 40m
Southwest
Deal found 5/28![Southwest logo]()
$413
This Alaska Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
mar. 6/232:16 pm
SJC
- STL
1 stop7h 43m
Alaska Airlines
sam. 6/275:37 pm
STL
- SJC
1 stop7h 44m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$515
This United Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
mar. 9/292:08 pm
SJC
- MLI
1 stop6h 30m
United Airlines
sam. 10/36:30 am
MLI
- SJC
1 stop7h 31m
United Airlines
Deal found 5/29![United Airlines logo]()
$449
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
mar. 6/2312:46 pm
SJC
- BMI
1 stop8h 01m
Delta
lun. 6/294:19 pm
BMI
- SJC
1 stop8h 38m
Delta
Deal found 5/30![Delta logo]()
$414
Last-minute flights from San Jose to IllinoisDiscover last-minute flight deals from San Jose to Illinois. Data last updated mai 31, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Illinois. Data last updated mai 31, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
sam. 6/207:13 am
SJC
- ORD
1 stop10h 24m
Alaska Airlines
mer. 6/247:59 pm
ORD
- SJC
1 stop15h 27m
Alaska Airlines
Deal found 5/29![Alaska Airlines logo]()
$345
This Travelocity deal was found by Cheapflights users on 5/26. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/233:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
mar. 6/306:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/26![Alaska Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 5/26. 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.
mar. 6/238:55 pm
SJC
- MDW
1 stop6h 30m
Southwest
mar. 6/305:35 am
MDW
- SJC
1 stop7h 05m
Southwest
Deal found 5/26![Southwest logo]()
$318
This CheapOair deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
mar. 6/233:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
ven. 6/267:59 pm
ORD
- SJC
1 stop15h 27m
Alaska Airlines
Deal found 5/29![Alaska Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 5/27. 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.
mer. 6/2412:46 pm
SJC
- ORD
1 stop9h 13m
Delta
mar. 6/306:55 am
ORD
- SJC
1 stop9h 16m
Delta
Deal found 5/27![Delta logo]()
$346
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
lun. 6/2910:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
mar. 7/145:30 am
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 5/29![Southwest logo]()
$340
This Frontier deal was found by Cheapflights users on 5/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/292:12 pm
SJC
- ORD
1 stop12h 55m
Frontier
sam. 7/47:20 am
ORD
- SJC
1 stop7h 57m
Frontier
Deal found 5/26![Frontier logo]()
$343
This Alaska Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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.
lun. 6/293:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
sam. 7/46:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/28![Alaska Airlines logo]()
$347
This Alaska Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
mar. 6/302:19 pm
SJC
- ORD
1 stop12h 41m
Alaska Airlines
sam. 7/46:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/29![Alaska Airlines logo]()
$310
This Alaska Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
mar. 6/303:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
mar. 7/76:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/31![Alaska Airlines logo]()
$313
This Expedia deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
mar. 6/303:15 pm
SJC
- ORD
1 stop6h 21m
Multiple Airlines
sam. 7/47:20 am
ORD
- SJC
1 stop7h 57m
Multiple Airlines
Deal found 5/31![Multiple Airlines logo]()
$326
This Alaska Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
mar. 6/303:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
ven. 7/32:20 pm
ORD
- SJC
1 stop6h 51m
Alaska Airlines
Deal found 5/29![Alaska Airlines 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 mai 31, 2026.
Search for one-way flight options from San Jose to Illinois. Find affordable one-way fares based on user searches. Data last updated mai 31, 2026.
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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.
lun. 8/2410:10 pm
SJC
- MDW
1 stop9h 49m
Delta
Deal found 5/28![Delta logo]()
$145
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
sam. 8/156:10 am
SJC
- ORD
1 stop6h 47m
Delta
Deal found 5/30![Delta logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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.
sam. 8/158:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Deal found 5/28![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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.
dim. 8/98:23 pm
SJC
- ORD
1 stop31h 54m
Frontier
Deal found 5/28![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
ven. 7/38:25 pm
SJC
- ORD
1 stop31h 54m
Frontier
Deal found 5/30![Frontier logo]()
$149
This Alaska Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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.
mar. 6/233:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
Deal found 5/28![Alaska Airlines logo]()
$152
This CheapOair deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
mer. 7/18:12 pm
SJC
- ORD
1 stop15h 09m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$162
This CheapOair deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
jeu. 8/67:13 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Deal found 5/31![Alaska Airlines logo]()
$165
This Super.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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.
lun. 8/178:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Deal found 5/28![Frontier logo]()
$168
This Frontier deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
sam. 7/48:25 pm
SJC
- ORD
1 stop7h 54m
Frontier
Deal found 5/29![Frontier logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
lun. 7/138:23 pm
SJC
- ORD
2 stops22h 29m
Frontier
Deal found 5/29![Frontier logo]()
$170
This Southwest deal was found by Cheapflights users on 5/27. 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.
mer. 7/1510:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 5/27![Southwest logo]()
$172
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 mai 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $298 (Southwest) |
One-way from | $145 (Delta) |
Popular in | March |
Cheapest in | February |
Average price | $497 |
Good round-trip deal | $491 or less |
Good one-way deal | $224 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 2,558,603 searches. Data last updated mai 31, 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 - ORD
SJCORD
San Jose
mer. 7/29
6:37 pm-5:00 am
1 stop8h 23m
Chicago O'Hare Intl
mar. 8/11
6:20 am-11:24 am
1 stop7h 04m
$318
San JoseChicago
SJC - MDW
SJCMDW
San Jose
mar. 7/14
1:30 pm-11:10 pm
1 stop7h 40m
Chicago Midway
mar. 7/21
5:25 am-11:25 am
2 stops8h 00m
$323
San JoseChicago
SJC - ORD
SJCORD
San Jose
jeu. 9/17
2:10 pm-8:35 pm
Nonstop4h 25m
Chicago O'Hare Intl
mar. 9/22
8:59 am-11:45 am
Nonstop4h 46m
$338
San JoseChicago
SJC - MDW
SJCMDW
San Jose
mar. 9/22
8:15 pm-4:30 am
1 stop6h 15m
Chicago Midway
jeu. 9/24
6:15 am-10:30 am
1 stop6h 15m
$345
San JoseMoline
SJC - MLI
SJCMLI
San Jose
ven. 9/4
12:37 pm-10:28 pm
1 stop7h 51m
Moline Quad-City
mer. 9/9
5:00 pm-10:41 pm
1 stop7h 41m
$349
San JoseMoline
SJC - MLI
SJCMLI
San Jose
ven. 9/4
10:10 pm-10:25 am
1 stop10h 15m
Moline Quad-City
jeu. 9/10
5:00 pm-10:41 pm
1 stop7h 41m
$349
San JoseBloomington
SJC - BMI
SJCBMI
San Jose
jeu. 9/24
6:59 am-10:24 pm
2 stops13h 25m
Bloomington-Normal
lun. 9/28
12:08 pm-10:13 pm
2 stops12h 05m
$359
San JoseChicago
SJC - MDW
SJCMDW
San Jose
jeu. 9/10
5:45 am-6:05 pm
2 stops10h 20m
Chicago Midway
dim. 9/13
10:35 am-6:37 pm
1 stop10h 02m
$363
San JoseChicago
SJC - ORD
SJCORD
San Jose
sam. 9/5
2:10 pm-8:35 pm
Nonstop4h 25m
Chicago O'Hare Intl
mar. 9/8
8:03 pm-10:50 pm
Nonstop4h 47m
$365
San JoseChicago
SJC - MDW
SJCMDW
San Jose
lun. 6/22
1:50 pm-11:25 pm
1 stop7h 35m
Chicago Midway
mer. 6/24
5:30 am-9:40 am
1 stop6h 10m
$370
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-RFD
SJC-STL
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-RFD
What is the cheapest month to book a flight from San Jose, California to Illinois?
Currently, March is the cheapest month in which you can book a flight from San Jose, California to Illinois (average of $95). Flying from San Jose, California to Illinois in April is currently the most expensive (average of $265). 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 mai 31, 2026.
It’s optimal to fly from San Jose, California to Illinois at noon. By choosing this option you can save up to 19% on the cost of your flight, compared to a flight in the evening.
Weekly flight availability from San Jose, California to Illinois
Explore weekly flight availability from San Jose to Illinois. 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 mai 31, 2026.
The most flights from SJC to USIL are scheduled on a Sunday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from San Jose, California to Illinois?
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 3 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 mai 31, 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.
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
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.
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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 mai 31, 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 7 airlines flying from San Jose to Illinois
Discover the top 7 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 2,558,603 searches. Data last updated mai 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$121 | Average$239 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$131 | Average$337 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$200 | Average$627 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$235 | Average$346 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$236 | Average$371 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$270 | Average$517 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$272 | Average$554 | FlexibilityNo cancel fee | On-time69% |