$75+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — ORD
Mar 24 — Mar 311
1 adult, Economy
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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
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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 February 22, 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 February 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Mon 3/167:42 pm
SJC
- STL
1 stop14h 33m
Frontier
Wed 3/258:12 pm
STL
- SJC
2 stops23h 55m
Frontier
Deal found 2/19![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Mon 3/167:42 pm
SJC
- STL
1 stop14h 33m
Frontier
Sun 3/298:06 pm
STL
- SJC
2 stops25h 19m
Frontier
Deal found 2/19![Frontier logo]()
$254
This Alaska Airlines deal was found by Cheapflights users on 2/21. 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 5/122:44 pm
SJC
- ORD
1 stop7h 15m
Alaska Airlines
Fri 5/152:10 pm
ORD
- SJC
1 stop10h 49m
Alaska Airlines
Deal found 2/21![Alaska Airlines logo]()
$256
This Alaska Airlines deal was found by Cheapflights users on 2/21. 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.
Mon 5/1112:44 pm
SJC
- ORD
1 stop8h 59m
Alaska Airlines
Thu 5/212:10 pm
ORD
- SJC
1 stop10h 49m
Alaska Airlines
Deal found 2/21![Alaska Airlines logo]()
$257
This CheapOair deal was found by Cheapflights users on 2/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2210:21 am
SJC
- ORD
2 stops11h 38m
Alaska Airlines
Mon 4/277:59 pm
ORD
- SJC
1 stop15h 45m
Alaska Airlines
Deal found 2/21![Alaska Airlines logo]()
$258
This Expedia deal was found by Cheapflights users on 2/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:45 pm
SJC
- ORD
1 stop9h 14m
Multiple Airlines
Sun 3/89:08 pm
ORD
- SJC
1 stop22h 59m
Multiple Airlines
Deal found 2/18![Multiple Airlines logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Mon 3/1610:20 am
SJC
- STL
2 stops45h 29m
Frontier
Mon 3/3012:14 pm
STL
- SJC
1 stop7h 53m
Frontier
Deal found 2/19![Frontier logo]()
$262
This CheapOair deal was found by Cheapflights users on 2/19. 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 3/127:00 am
SJC
- ORD
1 stop14h 59m
Alaska Airlines
Mon 3/237:59 pm
ORD
- SJC
1 stop19h 59m
Alaska Airlines
Deal found 2/19![Alaska Airlines logo]()
$263
This Frontier deal was found by Cheapflights users on 2/21. 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.
Mon 3/237:42 pm
SJC
- ORD
1 stop8h 26m
Frontier
Mon 3/3012:35 pm
ORD
- SJC
1 stop7h 32m
Frontier
Deal found 2/21![Frontier logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/158:20 pm
SJC
- STL
1 stop12h 59m
Frontier
Wed 3/258:12 pm
STL
- SJC
2 stops23h 55m
Frontier
Deal found 2/19![Frontier logo]()
$266
This Alaska Airlines deal was found by Cheapflights users on 2/21. 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.
Thu 5/712:44 pm
SJC
- ORD
1 stop8h 59m
Alaska Airlines
Thu 5/149:00 am
ORD
- SJC
1 stop7h 13m
Alaska Airlines
Deal found 2/21![Alaska Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Thu 5/76:57 pm
SJC
- ORD
1 stop8h 53m
Multiple Airlines
Sun 5/109:18 pm
ORD
- SJC
2 stops24h 07m
Multiple Airlines
Deal found 2/19![Multiple Airlines logo]()
$268
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 February 22, 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 February 22, 2026.
This Frontier deal was found by Cheapflights users on 2/18. 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 3/510:34 am
SJC
- STL
1 stop8h 52m
Frontier
Mon 3/912:14 pm
STL
- SJC
1 stop7h 53m
Frontier
Deal found 2/18![Frontier logo]()
$270
This Alaska Airlines deal was found by Cheapflights users on 2/19. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:06 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Mon 9/283:09 pm
ORD
- SJC
1 stop9h 03m
Alaska Airlines
Deal found 2/19![Alaska Airlines logo]()
$293
This Southwest deal was found by Cheapflights users on 2/18. 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 5/1310:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Fri 5/157:40 pm
MDW
- SJC
1 stop6h 15m
Southwest
Deal found 2/18![Southwest logo]()
$300
This United Airlines deal was found by Cheapflights users on 2/18. 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.
Wed 4/293:45 pm
SJC
- ORD
1 stop6h 45m
United Airlines
Thu 4/307:45 pm
ORD
- SJC
Nonstop4h 56m
United Airlines
Deal found 2/18![United Airlines logo]()
$300
This Delta deal was found by Cheapflights users on 2/18. 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.
Wed 3/258:35 pm
SJC
- MDW
2 stops10h 18m
Delta
Wed 4/112:47 pm
MDW
- SJC
1 stop10h 46m
Delta
Deal found 2/18![Delta logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:36 pm
SJC
- RFD
1 stop14h 24m
Multiple Airlines
Thu 4/1612:50 pm
RFD
- SJC
1 stop8h 26m
Multiple Airlines
Deal found 2/18![Multiple Airlines logo]()
$505
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Tue 3/246:00 am
SJC
- MLI
1 stop7h 01m
American Airlines
Tue 3/312:02 pm
MLI
- SJC
2 stops10h 30m
American Airlines
Deal found 2/20![American Airlines logo]()
$510
This Alaska Airlines deal was found by Cheapflights users on 2/18. 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.
Wed 8/121:19 pm
SJC
- ORD
1 stop8h 40m
Alaska Airlines
Mon 8/173:41 pm
ORD
- SJC
1 stop9h 53m
Alaska Airlines
Deal found 2/18![Alaska Airlines logo]()
$293
This Southwest deal was found by Cheapflights users on 2/18. 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 4/296:05 am
SJC
- MDW
1 stop7h 50m
Southwest
Thu 4/308:25 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 2/18![Southwest logo]()
$300
This United Airlines deal was found by Cheapflights users on 2/18. 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.
Wed 5/1312:56 pm
SJC
- ORD
1 stop10h 31m
United Airlines
Fri 5/157:55 pm
ORD
- SJC
Nonstop4h 56m
United Airlines
Deal found 2/18![United Airlines logo]()
$300
This Delta deal was found by Cheapflights users on 2/18. 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.
Tue 3/247:00 am
SJC
- ORD
2 stops9h 05m
Delta
Wed 4/17:10 pm
ORD
- SJC
1 stop6h 48m
Delta
Deal found 2/18![Delta logo]()
$302
This Alaska Airlines deal was found by Cheapflights users on 2/19. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:06 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Sun 9/276:00 am
ORD
- SJC
1 stop10h 30m
Alaska Airlines
Deal found 2/19![Alaska Airlines logo]()
$293
This Southwest deal was found by Cheapflights users on 2/19. 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 3/316:30 am
SJC
- MDW
1 stop6h 20m
Southwest
Tue 4/147:30 am
MDW
- SJC
2 stops8h 15m
Southwest
Deal found 2/19![Southwest logo]()
$302
This Delta deal was found by Cheapflights users on 2/18. 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.
Tue 3/318:35 pm
SJC
- MDW
2 stops10h 18m
Delta
Wed 4/1512:52 pm
MDW
- SJC
2 stops11h 09m
Delta
Deal found 2/18![Delta logo]()
$307
This United Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2410:55 pm
SJC
- MLI
1 stop9h 14m
United Airlines
Tue 3/313:20 pm
MLI
- SJC
1 stop9h 16m
United Airlines
Deal found 2/20![United Airlines logo]()
$309
This Alaska Airlines deal was found by Cheapflights users on 2/20. 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 5/142:00 pm
SJC
- ORD
1 stop7h 55m
Alaska Airlines
Tue 5/199:00 am
ORD
- SJC
1 stop7h 13m
Alaska Airlines
Deal found 2/20![Alaska Airlines logo]()
$298
This Delta deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/711:40 am
SJC
- STL
2 stops10h 41m
Delta
Wed 4/156:45 pm
STL
- SJC
1 stop6h 57m
Delta
Deal found 2/22![Delta logo]()
$308
This United Airlines deal was found by Cheapflights users on 2/20. 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 3/2310:55 pm
SJC
- MLI
1 stop9h 14m
United Airlines
Tue 3/313:20 pm
MLI
- SJC
1 stop9h 16m
United Airlines
Deal found 2/20![United Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 2/21. 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.
Mon 3/169:10 pm
SJC
- MDW
1 stop5h 50m
Southwest
Tue 3/2410:30 am
MDW
- SJC
1 stop8h 35m
Southwest
Deal found 2/21![Southwest logo]()
$310
This Alaska Airlines deal was found by Cheapflights users on 2/19. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/261:14 pm
SJC
- ORD
1 stop8h 45m
Alaska Airlines
Mon 9/286:00 am
ORD
- SJC
1 stop8h 11m
Alaska Airlines
Deal found 2/19![Alaska Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 2/18. 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.
Wed 4/111:40 am
SJC
- ORD
1 stop10h 12m
Delta
Fri 4/37:10 pm
ORD
- SJC
1 stop6h 48m
Delta
Deal found 2/18![Delta logo]()
$310
This Southwest deal was found by Cheapflights users on 2/18. 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.
Tue 3/2410:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 3/319:00 pm
MDW
- SJC
Nonstop4h 45m
Southwest
Deal found 2/18![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 2/18. 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.
Tue 3/317:15 am
SJC
- STL
2 stops15h 06m
Delta
Tue 4/142:20 pm
STL
- SJC
2 stops9h 55m
Delta
Deal found 2/18![Delta logo]()
$313
This Alaska Airlines deal was found by Cheapflights users on 2/18. 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.
Mon 4/67:05 pm
SJC
- STL
1 stop26h 54m
Alaska Airlines
Tue 4/143:50 pm
STL
- SJC
1 stop28h 21m
Alaska Airlines
Deal found 2/18![Alaska Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 2/19. 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 5/89:35 pm
SJC
- MDW
1 stop5h 50m
Southwest
Mon 5/118:25 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 2/19![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 2/18. 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.
Wed 4/19:40 am
SJC
- STL
1 stop5h 27m
Delta
Tue 4/142:20 pm
STL
- SJC
2 stops9h 55m
Delta
Deal found 2/18![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 2/18. 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.
Tue 5/1211:15 am
SJC
- ORD
2 stops9h 40m
Southwest
Mon 5/187:20 pm
ORD
- SJC
1 stop6h 35m
Southwest
Deal found 2/18![Southwest logo]()
$315
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Fri 3/62:07 pm
SJC
- MLI
1 stop6h 46m
American Airlines
Tue 3/1012:40 pm
MLI
- SJC
2 stops11h 52m
American Airlines
Deal found 2/19![American Airlines logo]()
$531
This Delta deal was found by Cheapflights users on 2/18. 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.
Tue 3/317:15 am
SJC
- STL
2 stops15h 06m
Delta
Sat 4/117:15 am
STL
- SJC
1 stop7h 16m
Delta
Deal found 2/18![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 2/18. 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 4/2412:55 pm
SJC
- MDW
1 stop7h 00m
Southwest
Fri 5/16:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Deal found 2/18![Southwest logo]()
$318
Last-minute flights from San Jose to IllinoisDiscover last-minute flight deals from San Jose to Illinois. Data last updated February 22, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Illinois. Data last updated February 22, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 2/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:45 pm
SJC
- ORD
1 stop9h 14m
Multiple Airlines
Sun 3/89:08 pm
ORD
- SJC
1 stop22h 59m
Multiple Airlines
Deal found 2/18![Multiple Airlines logo]()
$261
This Expedia deal was found by Cheapflights users on 2/19. 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.
Thu 3/510:24 am
SJC
- ORD
1 stop11h 35m
Multiple Airlines
Sun 3/87:39 pm
ORD
- SJC
1 stop25h 46m
Multiple Airlines
Deal found 2/19![Multiple Airlines logo]()
$267
This Frontier deal was found by Cheapflights users on 2/18. 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 3/510:34 am
SJC
- STL
1 stop8h 52m
Frontier
Mon 3/912:14 pm
STL
- SJC
1 stop7h 53m
Frontier
Deal found 2/18![Frontier logo]()
$270
This CheapOair deal was found by Cheapflights users on 2/19. 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 3/127:00 am
SJC
- ORD
1 stop14h 59m
Alaska Airlines
Mon 3/237:59 pm
ORD
- SJC
1 stop19h 59m
Alaska Airlines
Deal found 2/19![Alaska Airlines logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/158:20 pm
SJC
- STL
1 stop12h 59m
Frontier
Wed 3/258:12 pm
STL
- SJC
2 stops23h 55m
Frontier
Deal found 2/19![Frontier logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Mon 3/167:42 pm
SJC
- STL
1 stop14h 33m
Frontier
Wed 3/258:12 pm
STL
- SJC
2 stops23h 55m
Frontier
Deal found 2/19![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Mon 3/167:42 pm
SJC
- STL
1 stop14h 33m
Frontier
Sun 3/298:06 pm
STL
- SJC
2 stops25h 19m
Frontier
Deal found 2/19![Frontier logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Mon 3/1610:20 am
SJC
- STL
2 stops45h 29m
Frontier
Mon 3/3012:14 pm
STL
- SJC
1 stop7h 53m
Frontier
Deal found 2/19![Frontier logo]()
$262
This Expedia deal was found by Cheapflights users on 2/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/232:35 pm
SJC
- ORD
1 stop7h 24m
Multiple Airlines
Mon 3/3012:35 pm
ORD
- SJC
1 stop7h 32m
Multiple Airlines
Deal found 2/18![Multiple Airlines logo]()
$257
This Priceline deal was found by Cheapflights users on 2/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/237:42 pm
SJC
- ORD
1 stop8h 26m
Frontier
Mon 3/3012:35 pm
ORD
- SJC
1 stop7h 32m
Frontier
Deal found 2/18![Frontier logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/237:42 pm
SJC
- ORD
1 stop8h 26m
Multiple Airlines
Wed 4/17:45 pm
ORD
- SJC
2 stops25h 17m
Multiple Airlines
Deal found 2/18![Multiple Airlines logo]()
$269
This Alaska Airlines deal was found by Cheapflights users on 2/19. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/307:05 pm
SJC
- ORD
1 stop9h 34m
Alaska Airlines
Tue 3/314:13 pm
ORD
- SJC
1 stop19h 45m
Alaska Airlines
Deal found 2/19![Alaska Airlines logo]()
$268
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 February 22, 2026.
Search for one-way flight options from San Jose to Illinois. Find affordable one-way fares based on user searches. Data last updated February 22, 2026.
This Trip.com deal was found by Cheapflights users on 2/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/278:22 pm
SJC
- ORD
1 stop7h 46m
Frontier
Deal found 2/20![Frontier logo]()
$75
This Trip.com deal was found by Cheapflights users on 2/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/237:42 pm
SJC
- ORD
1 stop8h 26m
Frontier
Deal found 2/19![Frontier logo]()
$79
This Trip.com deal was found by Cheapflights users on 2/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/208:22 pm
SJC
- ORD
1 stop7h 28m
Multiple Airlines
Deal found 2/21![Multiple Airlines logo]()
$81
This Alaska Airlines deal was found by Cheapflights users on 2/20. 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 3/162:53 pm
SJC
- ORD
1 stop7h 06m
Alaska Airlines
Deal found 2/20![Alaska Airlines logo]()
$86
This Trip.com deal was found by Cheapflights users on 2/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:22 pm
SJC
- ORD
1 stop8h 25m
Frontier
Deal found 2/20![Frontier logo]()
$91
This Frontier deal was found by Cheapflights users on 2/20. 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.
Sun 4/198:22 pm
SJC
- ORD
1 stop8h 01m
Frontier
Deal found 2/20![Frontier logo]()
$95
This Trip.com deal was found by Cheapflights users on 2/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:57 pm
SJC
- ORD
1 stop9h 50m
Frontier
Deal found 2/19![Frontier logo]()
$97
This Frontier deal was found by Cheapflights users on 2/21. 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.
Mon 3/29:35 am
SJC
- STL
1 stop9h 38m
Frontier
Deal found 2/21![Frontier logo]()
$122
This CheapOair deal was found by Cheapflights users on 2/19. 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.
Sun 4/511:56 am
SJC
- STL
1 stop7h 21m
Frontier
Deal found 2/19![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 5/46:39 pm
SJC
- MDW
2 stops40h 21m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 4/276:39 pm
SJC
- MDW
2 stops40h 21m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$136
This Southwest deal was found by Cheapflights users on 2/19. 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 4/710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 2/19![Southwest logo]()
$139
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 February 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $248 (Kiwi.com) |
One-way from | $75 (Trip.com) |
Popular in | December |
Cheapest in | February |
Average price | $393 |
Good round-trip deal | $348 or less |
Good one-way deal | $209 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 February 22, 2026.
Use the filters below to find and compare flights from San Jose to Illinois that are best for you.
Fly from
San Jose
Fly to
Illinois
Route
Depart
Return
Price
San JoseSt. Louis
SJC - STL
SJCSTL
San Jose
Thu 3/5
10:34 am-9:26 pm
1 stop8h 52m
Lambert-St Louis
Mon 3/9
12:14 pm-6:07 pm
1 stop7h 53m
$270
San JoseChicago
SJC - ORD
SJCORD
San Jose
Fri 5/29
7:06 am-6:50 pm
1 stop9h 44m
Chicago O'Hare Intl
Mon 9/28
3:09 pm-10:12 pm
1 stop9h 03m
$293
San JoseChicago
SJC - ORD
SJCORD
San Jose
Wed 8/12
1:19 pm-11:59 pm
1 stop8h 40m
Chicago O'Hare Intl
Mon 8/17
3:41 pm-11:34 pm
1 stop9h 53m
$293
San JoseChicago
SJC - ORD
SJCORD
San Jose
Fri 5/29
7:06 am-6:50 pm
1 stop9h 44m
Chicago O'Hare Intl
Sun 9/27
6:00 am-2:30 pm
1 stop10h 30m
$293
San JoseChicago
SJC - ORD
SJCORD
San Jose
Thu 5/14
2:00 pm-11:55 pm
1 stop7h 55m
Chicago O'Hare Intl
Tue 5/19
9:00 am-2:13 pm
1 stop7h 13m
$298
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 5/13
10:55 pm-5:00 am
Nonstop4h 05m
Chicago Midway
Fri 5/15
7:40 pm-11:55 pm
1 stop6h 15m
$300
San JoseChicago
SJC - ORD
SJCORD
San Jose
Wed 4/29
3:45 pm-12:30 am
1 stop6h 45m
Chicago O'Hare Intl
Thu 4/30
7:45 pm-10:41 pm
Nonstop4h 56m
$300
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 4/29
6:05 am-3:55 pm
1 stop7h 50m
Chicago Midway
Thu 4/30
8:25 pm-11:00 pm
Nonstop4h 35m
$300
San JoseChicago
SJC - ORD
SJCORD
San Jose
Wed 5/13
12:56 pm-1:27 am
1 stop10h 31m
Chicago O'Hare Intl
Fri 5/15
7:55 pm-10:51 pm
Nonstop4h 56m
$300
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 3/25
8:35 pm-8:53 am
2 stops10h 18m
Chicago Midway
Wed 4/1
12:47 pm-9:33 pm
1 stop10h 46m
$302
Showing 1-10 of 60 results
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-STL
SJC-ORD
SJC-MDW
SJC-RFD
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-STL
SJC-ORD
SJC-MDW
SJC-RFD
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 $123). Flying from San Jose, California to Illinois in December is currently the most expensive (average of $233). 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 February 22, 2026.
It’s optimal to fly from San Jose, California to Illinois in the afternoon. By choosing this option you can save up to 21% on the cost of your flight, compared to a flight in the evening.
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 February 22, 2026.
Read through reviews of airlines operating flights from San Jose to Illinois, such as Alaska Airlines, Southwest, and Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.0
Comfort
7.8
Overall
8.0
Food
7.1
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Entertainment
7.0
Comfort
7.8
Overall
8.0
Food
7.1
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Entertainment
7.0
Comfort
7.8
Overall
8.0
Food
7.1
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Entertainment
7.0
Comfort
7.8
Overall
8.0
Food
7.1
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Entertainment
7.0
Comfort
7.8
Overall
8.0
Food
7.1
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Entertainment
7.0
Comfort
7.8
Overall
8.0
Food
7.1
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
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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Alternative routes for San Jose to Illinois
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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 February 22, 2026.
Popular flight searches
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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 February 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$62 | Average$244 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$125 | Average$239 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$170 | Average$315 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$200 | Average$616 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$208 | Average$399 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$297 | Average$519 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$331 | Average$511 | FlexibilityNo cancel fee | On-time63% |