$96+ 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 6/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — ORD
May 11 — May 181
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 April 11, 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 April 11, 2026.
This CheapOair deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/72:12 pm
SJC
- STL
1 stop28h 11m
Frontier
Sun 5/1012:36 pm
STL
- SJC
1 stop26h 41m
Frontier
Deal found 4/8![Frontier logo]()
$171
This CheapOair deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/72:12 pm
SJC
- STL
1 stop28h 11m
Frontier
Thu 5/1412:36 pm
STL
- SJC
1 stop26h 41m
Frontier
Deal found 4/9![Frontier logo]()
$196
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/510:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Wed 5/276:05 pm
MDW
- SJC
1 stop6h 55m
Southwest
Deal found 4/7![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/612:45 pm
SJC
- ORD
2 stops9h 10m
Southwest
Wed 5/137:45 am
ORD
- SJC
2 stops8h 00m
Southwest
Deal found 4/6![Southwest logo]()
$267
This Expedia deal was found by Cheapflights users on 4/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/812:59 pm
SJC
- ORD
1 stop8h 56m
Multiple Airlines
Thu 6/117:12 am
ORD
- SJC
1 stop8h 05m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$268
This Frontier deal was found by Cheapflights users on 4/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/112:12 pm
SJC
- ORD
1 stop13h 20m
Frontier
Sun 6/147:12 am
ORD
- SJC
1 stop8h 05m
Frontier
Deal found 4/10![Frontier logo]()
$270
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/2710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Sat 5/305:20 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 4/7![Southwest logo]()
$271
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/272:51 pm
SJC
- ORD
1 stop7h 06m
Delta
Sat 5/307:45 am
ORD
- SJC
1 stop7h 03m
Delta
Deal found 4/6![Delta logo]()
$271
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/510:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 5/127:30 am
MDW
- SJC
2 stops8h 15m
Southwest
Deal found 4/7![Southwest logo]()
$272
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:18 pm
SJC
- ORD
1 stop6h 14m
American Airlines
Tue 5/127:04 am
ORD
- SJC
1 stop7h 02m
American Airlines
Deal found 4/8![American Airlines logo]()
$272
This Expedia deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/3012:44 pm
SJC
- ORD
1 stop8h 59m
Multiple Airlines
Sun 5/37:21 pm
ORD
- SJC
1 stop26h 06m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/910:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Thu 5/145:25 pm
MDW
- SJC
1 stop7h 00m
Southwest
Deal found 4/8![Southwest logo]()
$275
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 April 11, 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 April 11, 2026.
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/66:45 am
SJC
- ORD
2 stops9h 19m
Delta
Tue 5/128:42 am
ORD
- SJC
2 stops10h 20m
Delta
Deal found 4/9![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/2710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Fri 5/2910:05 am
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 4/6![Southwest logo]()
$328
This Alaska Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 8/278:29 am
SJC
- ORD
1 stop8h 34m
Alaska Airlines
Mon 8/312:18 pm
ORD
- SJC
1 stop6h 51m
Alaska Airlines
Deal found 4/6![Alaska Airlines logo]()
$347
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 8/182:36 pm
SJC
- PIA
1 stop6h 44m
American Airlines
Wed 8/264:43 pm
PIA
- SJC
1 stop7h 13m
American Airlines
Deal found 4/8![American Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 4/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:30 am
SJC
- CMI
1 stop8h 58m
United Airlines
Sat 8/225:45 am
CMI
- SJC
1 stop7h 40m
United Airlines
Deal found 4/11![United Airlines logo]()
$447
This Southwest deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/2810:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 7/75:50 pm
MDW
- SJC
2 stops7h 10m
Southwest
Deal found 4/8![Southwest logo]()
$351
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/812:12 pm
SJC
- ORD
1 stop7h 41m
Delta
Tue 5/128:42 am
ORD
- SJC
2 stops10h 20m
Delta
Deal found 4/9![Delta logo]()
$367
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/272:34 pm
SJC
- MLI
1 stop6h 56m
American Airlines
Sat 5/304:42 pm
MLI
- SJC
1 stop8h 31m
American Airlines
Deal found 4/8![American Airlines logo]()
$369
This Alaska Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 7/107:13 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Mon 7/206:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 4/7![Alaska Airlines logo]()
$372
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/289:05 pm
SJC
- MDW
1 stop5h 55m
Southwest
Fri 5/296:00 am
MDW
- SJC
2 stops7h 45m
Southwest
Deal found 4/6![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 4/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:45 pm
SJC
- MLI
1 stop7h 45m
Delta
Tue 9/85:00 pm
MLI
- SJC
1 stop7h 41m
Delta
Deal found 4/11![Delta logo]()
$369
This American Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/612:46 pm
SJC
- MLI
2 stops9h 08m
American Airlines
Sat 5/912:49 pm
MLI
- SJC
2 stops12h 10m
American Airlines
Deal found 4/7![American Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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
- STL
1 stop7h 15m
Alaska Airlines
Wed 5/135:33 pm
STL
- SJC
1 stop7h 26m
Alaska Airlines
Deal found 4/6![Alaska Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/83:25 pm
SJC
- ORD
1 stop6h 30m
Southwest
Mon 5/118:00 am
ORD
- SJC
2 stops9h 05m
Southwest
Deal found 4/6![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 9/512:45 pm
SJC
- MLI
1 stop7h 45m
Delta
Mon 9/75:00 pm
MLI
- SJC
1 stop7h 41m
Delta
Deal found 4/9![Delta logo]()
$369
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/297:24 pm
SJC
- MLI
2 stops13h 15m
American Airlines
Sat 6/610:57 am
MLI
- SJC
2 stops13h 46m
American Airlines
Deal found 4/8![American Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 4/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:30 am
SJC
- ORD
Nonstop4h 27m
United Airlines
Sat 5/93:35 pm
ORD
- SJC
Nonstop4h 56m
United Airlines
Deal found 4/11![United Airlines logo]()
$468
This Delta deal was found by Cheapflights users on 4/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:45 pm
SJC
- MLI
1 stop7h 45m
Delta
Tue 9/85:00 pm
MLI
- SJC
1 stop7h 41m
Delta
Deal found 4/11![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/142:50 pm
SJC
- MDW
1 stop7h 05m
Southwest
Fri 5/156:00 am
MDW
- SJC
2 stops7h 45m
Southwest
Deal found 4/9![Southwest logo]()
$381
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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
- CMI
1 stop7h 56m
United Airlines
Sat 8/295:45 am
CMI
- SJC
1 stop7h 40m
United Airlines
Deal found 4/6![United Airlines logo]()
$478
This KAYAK deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:15 am
SJC
- ORD
1 stop8h 41m
Alaska Airlines
Tue 4/288:50 am
ORD
- SJC
1 stop7h 18m
Alaska Airlines
Deal found 4/6![Alaska Airlines logo]()
$441
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/810:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Mon 5/118:25 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 4/6![Southwest logo]()
$381
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/87:00 am
SJC
- MDW
2 stops9h 33m
Delta
Mon 5/111:22 pm
MDW
- SJC
2 stops10h 52m
Delta
Deal found 4/6![Delta logo]()
$386
This American Airlines deal was found by Cheapflights users on 4/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/252:02 pm
SJC
- MLI
1 stop7h 27m
American Airlines
Wed 4/293:48 pm
MLI
- SJC
1 stop8h 11m
American Airlines
Deal found 4/10![American Airlines logo]()
$439
This Alaska Airlines deal was found by Cheapflights users on 4/11. 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 4/266:15 am
SJC
- ORD
1 stop8h 41m
Alaska Airlines
Thu 4/303:52 pm
ORD
- SJC
1 stop9h 03m
Alaska Airlines
Deal found 4/11![Alaska Airlines logo]()
$457
This United Airlines deal was found by Cheapflights users on 4/10. 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.
Wed 8/196:30 am
SJC
- CMI
1 stop8h 58m
United Airlines
Sun 8/235:45 am
CMI
- SJC
1 stop7h 40m
United Airlines
Deal found 4/10![United Airlines logo]()
$513
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 9/410:20 pm
SJC
- MLI
1 stop10h 06m
Delta
Mon 9/75:00 pm
MLI
- SJC
1 stop7h 41m
Delta
Deal found 4/9![Delta logo]()
$394
This Southwest deal was found by Cheapflights users on 4/11. 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.
Thu 5/288:45 pm
SJC
- MDW
1 stop7h 05m
Southwest
Sun 5/315:10 am
MDW
- SJC
2 stops8h 00m
Southwest
Deal found 4/11![Southwest logo]()
$394
This American Airlines deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 6/611:48 am
SJC
- PIA
1 stop9h 45m
American Airlines
Sat 6/204:46 pm
PIA
- SJC
1 stop8h 27m
American Airlines
Deal found 4/9![American Airlines logo]()
$470
This United Airlines deal was found by Cheapflights users on 4/10. 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.
Sat 4/259:40 am
SJC
- PIA
1 stop7h 13m
United Airlines
Wed 4/295:35 pm
PIA
- SJC
1 stop7h 06m
United Airlines
Deal found 4/10![United Airlines logo]()
$519
Last-minute flights from San Jose to IllinoisDiscover last-minute flight deals from San Jose to Illinois. Data last updated April 11, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Illinois. Data last updated April 11, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/3012:44 pm
SJC
- ORD
1 stop8h 59m
Multiple Airlines
Sun 5/37:21 pm
ORD
- SJC
1 stop26h 06m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$273
This United Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3012:56 pm
SJC
- ORD
1 stop9h 49m
United Airlines
Mon 5/48:02 pm
ORD
- SJC
Nonstop4h 56m
United Airlines
Deal found 4/8![United Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 4/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:39 pm
SJC
- ORD
1 stop9h 11m
Frontier
Tue 5/59:37 pm
ORD
- SJC
2 stops40h 22m
Frontier
Deal found 4/10![Frontier logo]()
$270
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:18 pm
SJC
- ORD
1 stop6h 14m
American Airlines
Tue 5/127:04 am
ORD
- SJC
1 stop7h 02m
American Airlines
Deal found 4/8![American Airlines logo]()
$272
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/510:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Wed 5/276:05 pm
MDW
- SJC
1 stop6h 55m
Southwest
Deal found 4/7![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/510:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 5/127:30 am
MDW
- SJC
2 stops8h 15m
Southwest
Deal found 4/7![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/612:45 pm
SJC
- ORD
2 stops9h 10m
Southwest
Wed 5/137:45 am
ORD
- SJC
2 stops8h 00m
Southwest
Deal found 4/6![Southwest logo]()
$267
This CheapOair deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/72:12 pm
SJC
- STL
1 stop28h 11m
Frontier
Sun 5/1012:36 pm
STL
- SJC
1 stop26h 41m
Frontier
Deal found 4/8![Frontier logo]()
$171
This CheapOair deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/72:12 pm
SJC
- STL
1 stop28h 11m
Frontier
Thu 5/1412:36 pm
STL
- SJC
1 stop26h 41m
Frontier
Deal found 4/9![Frontier logo]()
$196
This Southwest deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/910:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Thu 5/145:25 pm
MDW
- SJC
1 stop7h 00m
Southwest
Deal found 4/8![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/2710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Sat 5/305:20 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 4/7![Southwest logo]()
$271
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/272:51 pm
SJC
- ORD
1 stop7h 06m
Delta
Sat 5/307:45 am
ORD
- SJC
1 stop7h 03m
Delta
Deal found 4/6![Delta logo]()
$271
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 April 11, 2026.
Search for one-way flight options from San Jose to Illinois. Find affordable one-way fares based on user searches. Data last updated April 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/812:57 pm
SJC
- STL
2 stops28h 26m
Frontier
Deal found 4/10![Frontier logo]()
$96
This CheapOair deal was found by Cheapflights users on 4/10. 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 5/72:12 pm
SJC
- STL
1 stop28h 11m
Frontier
Deal found 4/10![Frontier logo]()
$117
This CheapOair deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 4/179:41 pm
SJC
- STL
1 stop15h 40m
Frontier
Deal found 4/8![Frontier logo]()
$131
This CheapOair deal was found by Cheapflights users on 4/10. 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.
Mon 5/1112:57 pm
SJC
- ORD
1 stop15h 42m
Frontier
Deal found 4/10![Frontier logo]()
$137
This CheapOair deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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
- STL
1 stop22h 59m
Frontier
Deal found 4/6![Frontier logo]()
$138
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/69:25 pm
SJC
- MDW
1 stop6h 00m
Southwest
Deal found 4/7![Southwest logo]()
$139
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/36:20 am
SJC
- ORD
1 stop8h 31m
Delta
Deal found 4/6![Delta logo]()
$139
This Southwest deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/79:10 am
SJC
- MDW
1 stop6h 45m
Southwest
Deal found 4/8![Southwest logo]()
$143
This Southwest deal was found by Cheapflights users on 4/10. 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.
Thu 4/307:45 am
SJC
- ORD
1 stop9h 05m
Southwest
Deal found 4/10![Southwest logo]()
$143
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/56:45 am
SJC
- MDW
2 stops13h 43m
Delta
Deal found 4/7![Delta logo]()
$144
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/2810:10 am
SJC
- ORD
2 stops9h 08m
Delta
Deal found 4/6![Delta logo]()
$144
This Expedia deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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.
Sun 6/218:25 pm
SJC
- ORD
1 stop7h 54m
Frontier
Deal found 4/9![Frontier logo]()
$145
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 April 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $171 (CheapOair) |
One-way from | $96 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $470 |
Good round-trip deal | $386 or less |
Good one-way deal | $228 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 April 11, 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
Wed 5/6
6:45 am-6:04 pm
2 stops9h 19m
Chicago O'Hare Intl
Tue 5/12
8:42 am-5:02 pm
2 stops10h 20m
$267
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 5/27
10:55 pm-5:00 am
Nonstop4h 05m
Chicago Midway
Fri 5/29
10:05 am-2:15 pm
1 stop6h 10m
$328
San JoseChicago
SJC - ORD
SJCORD
San Jose
Thu 8/27
8:29 am-7:03 pm
1 stop8h 34m
Chicago O'Hare Intl
Mon 8/31
2:18 pm-7:09 pm
1 stop6h 51m
$347
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 5/28
10:55 pm-5:00 am
Nonstop4h 05m
Chicago Midway
Tue 7/7
5:50 pm-11:00 pm
2 stops7h 10m
$351
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 5/28
9:05 pm-5:00 am
1 stop5h 55m
Chicago Midway
Fri 5/29
6:00 am-11:45 am
2 stops7h 45m
$361
San JoseChicago
SJC - ORD
SJCORD
San Jose
Fri 5/8
3:25 pm-11:55 pm
1 stop6h 30m
Chicago O'Hare Intl
Mon 5/11
8:00 am-3:05 pm
2 stops9h 05m
$361
San JoseChicago
SJC - ORD
SJCORD
San Jose
Fri 5/8
12:12 pm-9:53 pm
1 stop7h 41m
Chicago O'Hare Intl
Tue 5/12
8:42 am-5:02 pm
2 stops10h 20m
$367
San JosePeoria
SJC - PIA
SJCPIA
San Jose
Tue 8/18
2:36 pm-11:20 pm
1 stop6h 44m
Greater Peoria
Wed 8/26
4:43 pm-9:56 pm
1 stop7h 13m
$369
San JoseMoline
SJC - MLI
SJCMLI
San Jose
Wed 5/27
2:34 pm-11:30 pm
1 stop6h 56m
Moline Quad-City
Sat 5/30
4:42 pm-11:13 pm
1 stop8h 31m
$369
San JoseMoline
SJC - MLI
SJCMLI
San Jose
Thu 9/3
12:45 pm-10:30 pm
1 stop7h 45m
Moline Quad-City
Tue 9/8
5:00 pm-10:41 pm
1 stop7h 41m
$369
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-STL
SJC-MDW
SJC-ORD
SJC-PIA
SJC-CMI
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from San Jose to Illinois
SJC-USIL
SJC-STL
SJC-MDW
SJC-ORD
SJC-PIA
What is the cheapest month to book a flight from San Jose, California to Illinois?
Currently, October is the cheapest month in which you can book a flight from San Jose, California to Illinois (average of $125). 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 April 11, 2026.
It’s optimal to fly from San Jose, California to Illinois in the afternoon. By choosing this option you can save up to 24% on the cost of your flight, compared to a flight in the evening.
How much does it cost to fly round-trip from San Jose, California to Illinois?
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 April 11, 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.
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
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 April 11, 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 April 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$121 | Average$239 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$131 | Average$294 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$170 | Average$315 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$200 | Average$621 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$208 | Average$417 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$280 | Average$525 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$330 | Average$515 | FlexibilityNo cancel fee | On-time63% |