$86+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — ORD
Apr 14 — Apr 211
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 March 15, 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 March 15, 2026.
This CheapOair deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:22 pm
SJC
- STL
1 stop19h 44m
Frontier
Wed 5/66:51 pm
STL
- SJC
1 stop20h 26m
Frontier
Deal found 3/12![Frontier logo]()
$242
This CheapOair deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/308:20 pm
SJC
- STL
1 stop12h 59m
Frontier
Thu 4/210:12 pm
STL
- SJC
1 stop23h 25m
Frontier
Deal found 3/12![Frontier logo]()
$275
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/1410:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Sat 4/1810:10 am
MDW
- SJC
2 stops8h 30m
Southwest
Deal found 3/12![Southwest logo]()
$277
This CheapOair deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
Tue 3/316:15 am
SJC
- ORD
1 stop15h 44m
Alaska Airlines
Mon 4/64:10 pm
ORD
- SJC
1 stop8h 00m
Alaska Airlines
Deal found 3/10![Alaska Airlines logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/712:23 pm
SJC
- ORD
1 stop28h 39m
Alaska Airlines
Wed 4/154:10 pm
ORD
- SJC
1 stop8h 00m
Alaska Airlines
Deal found 3/10![Alaska Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 5/712:57 pm
SJC
- ORD
1 stop8h 30m
Multiple Airlines
Mon 5/115:15 am
ORD
- SJC
1 stop8h 44m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” 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 5/78:40 pm
SJC
- MDW
1 stop7h 10m
Southwest
Mon 5/116:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Deal found 3/13![Southwest logo]()
$280
This CheapOair deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” 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 4/168:11 pm
SJC
- ORD
1 stop7h 57m
Frontier
Sat 4/187:21 pm
ORD
- SJC
1 stop26h 06m
Frontier
Deal found 3/13![Frontier logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” 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 4/168:11 pm
SJC
- ORD
2 stops25h 16m
Multiple Airlines
Mon 4/205:15 am
ORD
- SJC
1 stop16h 12m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$281
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 4/17:50 pm
SJC
- MDW
1 stop7h 50m
Southwest
Mon 4/611:50 am
MDW
- SJC
1 stop6h 35m
Southwest
Deal found 3/11![Southwest logo]()
$282
This Alaska Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/162:35 pm
SJC
- ORD
1 stop7h 24m
Alaska Airlines
Sat 4/186:00 am
ORD
- SJC
1 stop9h 35m
Alaska Airlines
Deal found 3/12![Alaska Airlines logo]()
$282
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/141:45 pm
SJC
- MDW
2 stops7h 35m
Southwest
Thu 4/166:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Deal found 3/12![Southwest logo]()
$283
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 March 15, 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 March 15, 2026.
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/143:15 pm
SJC
- MDW
1 stop6h 05m
Southwest
Thu 4/166:40 am
MDW
- SJC
1 stop6h 20m
Southwest
Deal found 3/12![Southwest logo]()
$282
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/256:32 pm
SJC
- STL
2 stops13h 10m
Delta
Tue 4/287:00 am
STL
- SJC
2 stops12h 52m
Delta
Deal found 3/10![Delta logo]()
$307
This American Airlines deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 4/72:02 pm
SJC
- STL
1 stop6h 57m
American Airlines
Sat 4/115:20 am
STL
- SJC
1 stop6h 47m
American Airlines
Deal found 3/15![American Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/146:30 am
SJC
- ORD
Nonstop4h 26m
United Airlines
Thu 4/167:46 pm
ORD
- SJC
Nonstop4h 55m
United Airlines
Deal found 3/12![United Airlines logo]()
$341
This Alaska Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/25:28 pm
SJC
- ORD
2 stops9h 34m
Alaska Airlines
Thu 8/66:22 am
ORD
- SJC
1 stop7h 02m
Alaska Airlines
Deal found 3/11![Alaska Airlines logo]()
$433
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/256:25 am
SJC
- STL
1 stop5h 55m
Southwest
Tue 4/281:45 pm
STL
- SJC
1 stop6h 30m
Southwest
Deal found 3/10![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 5/138:45 pm
SJC
- MDW
2 stops9h 57m
Delta
Sat 5/161:59 pm
MDW
- SJC
2 stops9h 42m
Delta
Deal found 3/12![Delta logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/47:32 pm
SJC
- RFD
1 stop14h 23m
Multiple Airlines
Sun 4/1212:50 pm
RFD
- SJC
2 stops22h 44m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$638
This Delta deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 5/138:45 pm
SJC
- MDW
2 stops9h 57m
Delta
Tue 5/199:23 am
MDW
- SJC
2 stops9h 52m
Delta
Deal found 3/14![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2410:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Wed 5/275:15 pm
MDW
- SJC
1 stop6h 45m
Southwest
Deal found 3/10![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/133:45 pm
SJC
- ORD
1 stop6h 44m
United Airlines
Thu 4/237:46 pm
ORD
- SJC
Nonstop4h 55m
United Airlines
Deal found 3/10![United Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 4/2410:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Mon 4/278:25 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 3/11![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 5/286:15 am
SJC
- ORD
1 stop8h 36m
Delta
Sun 5/318:42 am
ORD
- SJC
2 stops12h 37m
Delta
Deal found 3/10![Delta logo]()
$372
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
Fri 7/101:10 pm
SJC
- ORD
1 stop8h 05m
United Airlines
Tue 7/147:45 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Deal found 3/10![United Airlines logo]()
$417
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/1810:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Sun 4/266:00 am
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 3/10![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 6/510:00 pm
SJC
- MLI
1 stop10h 20m
Delta
Mon 6/85:00 pm
MLI
- SJC
1 stop7h 53m
Delta
Deal found 3/12![Delta logo]()
$374
This American Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 7/182:35 pm
SJC
- EVV
1 stop6h 56m
American Airlines
Mon 7/275:14 pm
EVV
- SJC
1 stop7h 46m
American Airlines
Deal found 3/11![American Airlines logo]()
$523
This Southwest deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 4/202:15 pm
SJC
- STL
1 stop7h 35m
Southwest
Sat 4/254:45 pm
STL
- SJC
1 stop6h 05m
Southwest
Deal found 3/14![Southwest logo]()
$358
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 8/252:09 pm
SJC
- PIA
1 stop6h 43m
United Airlines
Sat 8/292:33 pm
PIA
- SJC
1 stop10h 08m
United Airlines
Deal found 3/10![United Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 5/2911:00 pm
SJC
- MDW
1 stop7h 43m
Delta
Mon 6/15:08 pm
MDW
- SJC
1 stop7h 47m
Delta
Deal found 3/14![Delta logo]()
$376
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/178:15 pm
SJC
- MDW
1 stop7h 10m
Southwest
Mon 4/206:25 pm
MDW
- SJC
1 stop7h 00m
Southwest
Deal found 3/10![Southwest logo]()
$367
This United Airlines deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” 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 4/216:30 am
SJC
- ORD
Nonstop4h 26m
United Airlines
Fri 4/247:46 pm
ORD
- SJC
Nonstop4h 55m
United Airlines
Deal found 3/13![United Airlines logo]()
$446
This Delta deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 5/97:00 am
SJC
- ORD
2 stops12h 50m
Delta
Sun 5/108:42 am
ORD
- SJC
2 stops10h 20m
Delta
Deal found 3/15![Delta logo]()
$386
This American Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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.
Wed 3/252:08 pm
SJC
- EVV
1 stop6h 38m
American Airlines
Sat 3/283:50 pm
EVV
- SJC
1 stop7h 31m
American Airlines
Deal found 3/12![American Airlines logo]()
$577
This United Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 8/122:09 pm
SJC
- CMI
1 stop7h 56m
United Airlines
Wed 8/195:45 am
CMI
- SJC
1 stop7h 40m
United Airlines
Deal found 3/14![United Airlines logo]()
$448
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 4/302:40 pm
SJC
- MDW
1 stop6h 00m
Southwest
Sun 5/39:20 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 3/15![Southwest logo]()
$376
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/245:50 am
SJC
- MDW
2 stops10h 43m
Delta
Wed 5/271:59 pm
MDW
- SJC
2 stops11h 42m
Delta
Deal found 3/10![Delta logo]()
$394
This Kiwi.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/47:32 pm
SJC
- RFD
1 stop14h 23m
Multiple Airlines
Thu 4/1612:50 pm
RFD
- SJC
1 stop8h 26m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$702
This United Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 8/126:30 am
SJC
- CMI
1 stop8h 58m
United Airlines
Tue 8/185:45 am
CMI
- SJC
1 stop7h 40m
United Airlines
Deal found 3/14![United Airlines logo]()
$448
This American Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/912:46 pm
SJC
- BMI
2 stops9h 06m
American Airlines
Thu 4/166:00 am
BMI
- SJC
1 stop9h 12m
American Airlines
Deal found 3/12![American Airlines logo]()
$597
Last-minute flights from San Jose to IllinoisDiscover last-minute flight deals from San Jose to Illinois. Data last updated March 15, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Illinois. Data last updated March 15, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/308:20 pm
SJC
- STL
1 stop12h 59m
Frontier
Thu 4/210:12 pm
STL
- SJC
1 stop23h 25m
Frontier
Deal found 3/12![Frontier logo]()
$275
This CheapOair deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
Tue 3/316:15 am
SJC
- ORD
1 stop15h 44m
Alaska Airlines
Mon 4/64:10 pm
ORD
- SJC
1 stop8h 00m
Alaska Airlines
Deal found 3/10![Alaska Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 4/17:50 pm
SJC
- MDW
1 stop7h 50m
Southwest
Mon 4/611:50 am
MDW
- SJC
1 stop6h 35m
Southwest
Deal found 3/11![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 4/610:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Mon 4/138:25 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 3/15![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 4/610:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Thu 4/98:25 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 3/11![Southwest logo]()
$287
This Alaska Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/712:23 pm
SJC
- ORD
1 stop28h 39m
Alaska Airlines
Wed 4/154:10 pm
ORD
- SJC
1 stop8h 00m
Alaska Airlines
Deal found 3/10![Alaska Airlines logo]()
$278
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/1410:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Sat 4/2510:10 am
MDW
- SJC
2 stops8h 30m
Southwest
Deal found 3/12![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/141:45 pm
SJC
- MDW
2 stops7h 35m
Southwest
Thu 4/166:15 am
MDW
- SJC
1 stop6h 15m
Southwest
Deal found 3/12![Southwest logo]()
$283
This CheapOair deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” 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 4/168:11 pm
SJC
- ORD
1 stop7h 57m
Frontier
Sat 4/187:21 pm
ORD
- SJC
1 stop26h 06m
Frontier
Deal found 3/13![Frontier logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” 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 4/168:11 pm
SJC
- ORD
2 stops25h 16m
Multiple Airlines
Mon 4/205:15 am
ORD
- SJC
1 stop16h 12m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$281
This Alaska Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/1612:23 pm
SJC
- ORD
1 stop9h 36m
Alaska Airlines
Wed 4/226:00 am
ORD
- SJC
1 stop9h 50m
Alaska Airlines
Deal found 3/12![Alaska Airlines logo]()
$282
This CheapOair deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/306:43 am
SJC
- ORD
1 stop10h 20m
Alaska Airlines
Tue 5/56:00 am
ORD
- SJC
2 stops15h 04m
Alaska Airlines
Deal found 3/10![Alaska Airlines logo]()
$283
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 March 15, 2026.
Search for one-way flight options from San Jose to Illinois. Find affordable one-way fares based on user searches. Data last updated March 15, 2026.
This CheapOair deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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.
Tue 4/217:00 am
SJC
- ORD
1 stop9h 40m
Alaska Airlines
Deal found 3/11![Alaska Airlines logo]()
$86
This Vakatrip deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Vakatrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2810:21 am
SJC
- ORD
1 stop6h 42m
Alaska Airlines
Deal found 3/14![Alaska Airlines logo]()
$90
This CheapOair deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/138:39 pm
SJC
- ORD
1 stop15h 42m
Alaska Airlines
Deal found 3/11![Alaska Airlines logo]()
$91
This Alaska Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 5/112:21 pm
SJC
- ORD
1 stop7h 22m
Alaska Airlines
Deal found 3/14![Alaska Airlines logo]()
$96
This CheapOair deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 5/62:44 pm
SJC
- ORD
1 stop7h 15m
Alaska Airlines
Deal found 3/12![Alaska Airlines logo]()
$98
This CheapOair deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/196:39 pm
SJC
- ORD
1 stop9h 41m
Frontier
Deal found 3/10![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 5/112:12 pm
SJC
- MDW
2 stops29h 50m
Frontier
Deal found 3/11![Frontier logo]()
$107
This Booking.com deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1012:57 pm
SJC
- ORD
1 stop15h 42m
Frontier
Deal found 3/15![Frontier logo]()
$111
This Expedia deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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.
Tue 5/129:38 am
SJC
- ORD
1 stop17h 27m
Alaska Airlines
Deal found 3/14![Alaska Airlines logo]()
$113
This CheapOair deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/2310:21 am
SJC
- ORD
1 stop6h 42m
Alaska Airlines
Deal found 3/12![Alaska Airlines logo]()
$114
This CheapOair deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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.
Fri 5/297:06 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Deal found 3/12![Alaska Airlines logo]()
$115
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/810:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 3/12![Southwest logo]()
$119
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 March 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $242 (CheapOair) |
One-way from | $86 (CheapOair) |
Popular in | December |
Cheapest in | February |
Average price | $460 |
Good round-trip deal | $377 or less |
Good one-way deal | $193 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 March 15, 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 - MDW
SJCMDW
San Jose
Tue 4/14
3:15 pm-11:20 pm
1 stop6h 05m
Chicago Midway
Thu 4/16
6:40 am-11:00 am
1 stop6h 20m
$282
San JoseSt. Louis
SJC - STL
SJCSTL
San Jose
Sat 4/25
6:32 pm-9:42 am
2 stops13h 10m
Lambert-St Louis
Tue 4/28
7:00 am-5:52 pm
2 stops12h 52m
$307
San JoseSt. Louis
SJC - STL
SJCSTL
San Jose
Sat 4/25
6:25 am-2:20 pm
1 stop5h 55m
Lambert-St Louis
Tue 4/28
1:45 pm-6:15 pm
1 stop6h 30m
$312
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 5/13
8:45 pm-8:42 am
2 stops9h 57m
Chicago Midway
Sat 5/16
1:59 pm-9:41 pm
2 stops9h 42m
$312
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 5/13
8:45 pm-8:42 am
2 stops9h 57m
Chicago Midway
Tue 5/19
9:23 am-5:15 pm
2 stops9h 52m
$315
San JoseSt. Louis
SJC - STL
SJCSTL
San Jose
Tue 4/7
2:02 pm-10:59 pm
1 stop6h 57m
Lambert-St Louis
Sat 4/11
5:20 am-10:07 am
1 stop6h 47m
$317
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Sun 5/24
10:55 pm-5:00 am
Nonstop4h 05m
Chicago Midway
Wed 5/27
5:15 pm-10:00 pm
1 stop6h 45m
$322
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 4/14
6:30 am-12:56 pm
Nonstop4h 26m
Chicago O'Hare Intl
Thu 4/16
7:46 pm-10:41 pm
Nonstop4h 55m
$341
Quickest round-trip
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 4/24
10:55 pm-5:00 am
Nonstop4h 05m
Chicago Midway
Mon 4/27
8:25 pm-11:00 pm
Nonstop4h 35m
$347
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Sat 4/18
10:55 pm-5:00 am
Nonstop4h 05m
Chicago Midway
Sun 4/26
6:00 am-10:10 am
1 stop6h 10m
$357
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-MDW
SJC-STL
SJC-ORD
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-MDW
SJC-STL
SJC-ORD
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 $115). 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 March 15, 2026.
It’s optimal to fly from San Jose, California to Illinois in the afternoon. 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 March 15, 2026.
The most flights from SJC to USIL are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
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 March 15, 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.
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
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 March 15, 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 March 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$121 | Average$239 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$131 | Average$244 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$170 | Average$315 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$200 | Average$578 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$208 | Average$407 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$297 | Average$523 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$330 | Average$514 | FlexibilityNo cancel fee | On-time63% |