$136+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — ORD
Aug 25 — Sep 11
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 July 26, 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 July 26, 2026.
This Travelocity deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/141:38 pm
SJC
- STL
1 stop19h 54m
Frontier
Wed 9/1612:17 pm
STL
- SJC
1 stop26h 26m
Frontier
Deal found 7/24![Frontier logo]()
$252
This Orbitz deal was found by Cheapflights users on 7/21. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:24 pm
SJC
- STL
1 stop19h 27m
Frontier
Sat 9/2612:46 pm
STL
- SJC
1 stop21h 27m
Frontier
Deal found 7/21![Frontier logo]()
$256
This Expedia deal was found by Cheapflights users on 7/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:24 pm
SJC
- STL
1 stop19h 27m
Frontier
Sun 9/2012:46 pm
STL
- SJC
1 stop26h 43m
Frontier
Deal found 7/21![Frontier logo]()
$257
This CheapOair deal was found by Cheapflights users on 7/21. 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.
Thu 8/201:02 pm
SJC
- STL
1 stop26h 48m
Frontier
Sun 8/236:45 pm
STL
- SJC
1 stop20h 37m
Frontier
Deal found 7/21![Frontier logo]()
$262
This Orbitz deal was found by Cheapflights users on 7/21. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/82:24 pm
SJC
- STL
1 stop8h 53m
Multiple Airlines
Tue 10/137:02 am
STL
- SJC
2 stops17h 50m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$264
This CheapOair deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/242:24 pm
SJC
- STL
1 stop19h 27m
Frontier
Sun 9/2712:46 pm
STL
- SJC
1 stop26h 43m
Frontier
Deal found 7/24![Frontier logo]()
$268
This Travelocity deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/148:17 pm
SJC
- STL
2 stops18h 53m
Alaska Airlines
Wed 9/166:29 am
STL
- SJC
2 stops14h 40m
Alaska Airlines
Deal found 7/24![Alaska Airlines logo]()
$284
This CheapOair deal was found by Cheapflights users on 7/21. 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.
Fri 10/232:24 pm
SJC
- STL
1 stop8h 53m
Frontier
Sun 10/255:19 pm
STL
- SJC
1 stop22h 10m
Frontier
Deal found 7/21![Frontier logo]()
$286
This Expedia deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:17 pm
SJC
- STL
2 stops18h 53m
Alaska Airlines
Tue 9/16:35 am
STL
- SJC
2 stops13h 29m
Alaska Airlines
Deal found 7/23![Alaska Airlines logo]()
$294
This Expedia deal was found by Cheapflights users on 7/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/252:24 pm
SJC
- STL
1 stop19h 27m
Frontier
Sun 9/2712:46 pm
STL
- SJC
1 stop26h 43m
Frontier
Deal found 7/21![Frontier logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 10/11:38 pm
SJC
- ORD
1 stop14h 00m
Frontier
Sun 10/48:55 pm
ORD
- SJC
2 stops24h 58m
Frontier
Deal found 7/25![Frontier logo]()
$318
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:00 am
SJC
- MDW
2 stops7h 25m
Southwest
Mon 10/57:00 am
MDW
- SJC
1 stop7h 45m
Southwest
Deal found 7/23![Southwest logo]()
$319
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 July 26, 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 July 26, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:29 am
SJC
- ORD
2 stops13h 30m
Alaska Airlines
Mon 9/218:17 pm
ORD
- SJC
1 stop15h 06m
Alaska Airlines
Deal found 7/23![Alaska Airlines logo]()
$320
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:35 pm
SJC
- STL
2 stops11h 13m
Delta
Wed 11/186:30 am
STL
- SJC
2 stops12h 27m
Delta
Deal found 7/23![Delta logo]()
$323
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/262:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Thu 8/278:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 7/24![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:00 pm
SJC
- STL
1 stop6h 20m
Southwest
Wed 8/199:05 am
STL
- SJC
2 stops7h 25m
Southwest
Deal found 7/21![Southwest logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/239:03 pm
SJC
- RFD
2 stops21h 36m
Multiple Airlines
Sun 9/279:29 pm
RFD
- SJC
1 stop18h 00m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 11/612:58 pm
SJC
- STL
1 stop8h 58m
American Airlines
Mon 11/95:00 am
STL
- SJC
1 stop8h 06m
American Airlines
Deal found 7/25![American Airlines logo]()
$401
This Alaska Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 9/78:29 am
SJC
- ORD
1 stop13h 30m
Alaska Airlines
Thu 9/107:20 am
ORD
- SJC
1 stop8h 25m
Alaska Airlines
Deal found 7/25![Alaska Airlines logo]()
$320
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:45 am
SJC
- ORD
1 stop8h 45m
United Airlines
Tue 8/258:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 7/22![United Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/1312:10 pm
SJC
- MDW
2 stops7h 30m
Southwest
Wed 9/1612:20 pm
MDW
- SJC
1 stop7h 55m
Southwest
Deal found 7/24![Southwest logo]()
$352
This Delta deal was found by Cheapflights users on 7/22. 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.
Thu 8/2012:35 pm
SJC
- MDW
1 stop8h 01m
Delta
Thu 8/275:10 pm
MDW
- SJC
1 stop7h 48m
Delta
Deal found 7/22![Delta logo]()
$352
This Alaska Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/158:17 pm
SJC
- STL
2 stops18h 53m
Alaska Airlines
Thu 9/176:08 pm
STL
- SJC
1 stop16h 54m
Alaska Airlines
Deal found 7/22![Alaska Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/82:24 pm
SJC
- RFD
2 stops19h 03m
Multiple Airlines
Sun 10/119:33 pm
RFD
- SJC
1 stop17h 56m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$367
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/148:30 pm
SJC
- MDW
1 stop7h 10m
Southwest
Mon 8/178:50 am
MDW
- SJC
1 stop6h 45m
Southwest
Deal found 7/23![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 7/22. 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.
Fri 8/2112:35 pm
SJC
- MDW
1 stop8h 01m
Delta
Tue 9/11:51 pm
MDW
- SJC
1 stop8h 33m
Delta
Deal found 7/22![Delta logo]()
$372
This Alaska Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/59:15 am
SJC
- ORD
2 stops12h 44m
Alaska Airlines
Thu 10/87:49 pm
ORD
- SJC
1 stop16h 05m
Alaska Airlines
Deal found 7/23![Alaska Airlines logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:03 pm
SJC
- RFD
2 stops21h 36m
Multiple Airlines
Sun 9/209:29 pm
RFD
- SJC
1 stop18h 00m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$406
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/119:35 am
SJC
- STL
2 stops8h 20m
Southwest
Sat 8/158:25 am
STL
- SJC
2 stops8h 45m
Southwest
Deal found 7/21![Southwest logo]()
$373
This United Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 8/212:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Tue 9/18:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 7/25![United Airlines logo]()
$415
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/86:00 am
SJC
- PIA
1 stop7h 53m
American Airlines
Wed 8/127:11 am
PIA
- SJC
1 stop8h 29m
American Airlines
Deal found 7/24![American Airlines logo]()
$474
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 10/212:51 pm
SJC
- MDW
1 stop7h 53m
Delta
Tue 10/612:45 pm
MDW
- SJC
1 stop10h 40m
Delta
Deal found 7/25![Delta logo]()
$401
This Alaska Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 10/810:37 am
SJC
- STL
1 stop11h 22m
Alaska Airlines
Tue 10/137:02 am
STL
- SJC
2 stops17h 50m
Alaska Airlines
Deal found 7/24![Alaska Airlines logo]()
$366
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Fri 11/2710:15 am
MDW
- SJC
2 stops8h 00m
Southwest
Deal found 7/25![Southwest logo]()
$375
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:51 pm
SJC
- ORD
1 stop7h 55m
United Airlines
Fri 8/288:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 7/22![United Airlines logo]()
$427
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/510:50 pm
SJC
- MDW
1 stop9h 02m
Delta
Thu 10/81:00 pm
MDW
- SJC
1 stop10h 25m
Delta
Deal found 7/24![Delta logo]()
$403
This Alaska Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 8/149:09 am
SJC
- ORD
1 stop7h 48m
Alaska Airlines
Tue 8/186:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 7/25![Alaska Airlines logo]()
$372
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/262:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Fri 8/288:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 7/24![United Airlines logo]()
$427
This Alaska Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:08 am
SJC
- ORD
1 stop9h 51m
Alaska Airlines
Fri 11/277:26 am
ORD
- SJC
1 stop8h 24m
Alaska Airlines
Deal found 7/25![Alaska Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:05 pm
SJC
- MDW
1 stop8h 25m
Southwest
Tue 8/112:15 pm
MDW
- SJC
1 stop5h 50m
Southwest
Deal found 7/21![Southwest logo]()
$417
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 10/110:50 pm
SJC
- MDW
1 stop8h 59m
Delta
Sat 10/39:59 am
MDW
- SJC
1 stop9h 47m
Delta
Deal found 7/25![Delta logo]()
$428
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/72:32 pm
SJC
- ORD
1 stop6h 17m
United Airlines
Tue 8/119:00 am
ORD
- SJC
Nonstop4h 46m
United Airlines
Deal found 7/21![United Airlines logo]()
$447
Last-minute flights from San Jose to IllinoisDiscover last-minute flight deals from San Jose to Illinois. Data last updated July 26, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Illinois. Data last updated July 26, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 7/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/72:12 pm
SJC
- ORD
1 stop13h 25m
Multiple Airlines
Thu 8/136:20 am
ORD
- SJC
1 stop7h 04m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$323
This CheapOair deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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.
Sat 8/82:12 pm
SJC
- ORD
1 stop13h 25m
Frontier
Sun 8/238:11 pm
ORD
- SJC
1 stop19h 11m
Frontier
Deal found 7/24![Frontier logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/108:23 pm
SJC
- ORD
1 stop7h 54m
Multiple Airlines
Tue 8/252:18 pm
ORD
- SJC
1 stop6h 51m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/108:23 pm
SJC
- ORD
1 stop7h 54m
Multiple Airlines
Sat 8/226:01 am
ORD
- SJC
1 stop6h 58m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$326
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/132:50 pm
SJC
- MDW
1 stop6h 30m
Southwest
Mon 8/177:10 am
MDW
- SJC
2 stops7h 40m
Southwest
Deal found 7/22![Southwest logo]()
$323
This KAYAK deal was found by Cheapflights users on 7/22. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:45 pm
SJC
- ORD
1 stop6h 44m
Delta
Thu 8/206:00 am
ORD
- SJC
1 stop8h 27m
Delta
Deal found 7/22![Delta logo]()
$320
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:51 pm
SJC
- ORD
1 stop7h 55m
United Airlines
Tue 8/258:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 7/23![United Airlines logo]()
$321
This CheapOair deal was found by Cheapflights users on 7/21. 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.
Thu 8/201:02 pm
SJC
- STL
1 stop26h 48m
Frontier
Sun 8/236:45 pm
STL
- SJC
1 stop20h 37m
Frontier
Deal found 7/21![Frontier logo]()
$262
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:51 pm
SJC
- ORD
1 stop9h 08m
United Airlines
Thu 8/278:03 pm
ORD
- SJC
Nonstop4h 47m
United Airlines
Deal found 7/23![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:00 pm
SJC
- MDW
1 stop7h 30m
Southwest
Fri 8/288:50 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 7/26![Southwest logo]()
$325
This Expedia deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:17 pm
SJC
- STL
2 stops18h 53m
Alaska Airlines
Tue 9/16:35 am
STL
- SJC
2 stops13h 29m
Alaska Airlines
Deal found 7/23![Alaska Airlines logo]()
$294
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3011:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Tue 9/110:20 am
MDW
- SJC
Nonstop4h 25m
Southwest
Deal found 7/22![Southwest logo]()
$327
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 July 26, 2026.
Search for one-way flight options from San Jose to Illinois. Find affordable one-way fares based on user searches. Data last updated July 26, 2026.
This CheapOair deal was found by Cheapflights users on 7/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/179:10 am
SJC
- STL
1 stop24h 41m
Frontier
Deal found 7/22![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:03 pm
SJC
- STL
2 stops10h 37m
Frontier
Deal found 7/21![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:14 pm
SJC
- MDW
2 stops22h 17m
Frontier
Deal found 7/23![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 8/168:23 pm
SJC
- ORD
1 stop7h 54m
Frontier
Deal found 7/25![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:03 pm
SJC
- MDW
2 stops22h 55m
Frontier
Deal found 7/22![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:23 pm
SJC
- RFD
3 stops39h 00m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 10/19:10 am
SJC
- ORD
2 stops13h 13m
Frontier
Deal found 7/25![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:14 pm
SJC
- MDW
2 stops22h 17m
Frontier
Deal found 7/21![Frontier logo]()
$163
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:10 pm
SJC
- ORD
Nonstop4h 25m
United Airlines
Deal found 7/22![United Airlines logo]()
$164
This Alaska Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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.
Sat 8/156:37 pm
SJC
- ORD
1 stop8h 23m
Alaska Airlines
Deal found 7/24![Alaska Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/152:12 pm
SJC
- ORD
1 stop13h 25m
Frontier
Deal found 7/23![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 8/242:17 pm
SJC
- MDW
2 stops18h 38m
Frontier
Deal found 7/25![Frontier logo]()
$168
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 July 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $252 (Travelocity) |
One-way from | $136 (CheapOair) |
Popular in | December |
Cheapest in | February |
Average price | $510 |
Good round-trip deal | $387 or less |
Good one-way deal | $234 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 July 26, 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 9/16
8:29 am-11:59 pm
2 stops13h 30m
Chicago O'Hare Intl
Mon 9/21
8:17 pm-9:23 am
1 stop15h 06m
$320
San JoseChicago
SJC - ORD
SJCORD
San Jose
Mon 9/7
8:29 am-11:59 pm
1 stop13h 30m
Chicago O'Hare Intl
Thu 9/10
7:20 am-1:45 pm
1 stop8h 25m
$320
San JoseSt. Louis
SJC - STL
SJCSTL
San Jose
Tue 9/15
8:17 pm-5:10 pm
2 stops18h 53m
Lambert-St Louis
Thu 9/17
6:08 pm-9:02 am
1 stop16h 54m
$321
San JoseSt. Louis
SJC - STL
SJCSTL
San Jose
Mon 11/16
7:35 pm-8:48 am
2 stops11h 13m
Lambert-St Louis
Wed 11/18
6:30 am-4:57 pm
2 stops12h 27m
$323
Quickest round-trip
San JoseChicago
SJC - ORD
SJCORD
San Jose
Wed 8/26
2:10 pm-8:35 pm
Nonstop4h 25m
Chicago O'Hare Intl
Thu 8/27
8:03 pm-10:50 pm
Nonstop4h 47m
$337
San JoseChicago
SJC - ORD
SJCORD
San Jose
Sat 8/22
8:45 am-7:30 pm
1 stop8h 45m
Chicago O'Hare Intl
Tue 8/25
8:03 pm-10:50 pm
Nonstop4h 47m
$347
San JoseChicago
SJC - ORD
SJCORD
San Jose
Mon 10/5
9:15 am-11:59 pm
2 stops12h 44m
Chicago O'Hare Intl
Thu 10/8
7:49 pm-9:54 am
1 stop16h 05m
$350
San JoseSt. Louis
SJC - STL
SJCSTL
San Jose
Tue 8/18
12:00 pm-8:20 pm
1 stop6h 20m
Lambert-St Louis
Wed 8/19
9:05 am-2:30 pm
2 stops7h 25m
$352
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Sun 9/13
12:10 pm-9:40 pm
2 stops7h 30m
Chicago Midway
Wed 9/16
12:20 pm-6:15 pm
1 stop7h 55m
$352
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 8/20
12:35 pm-10:36 pm
1 stop8h 01m
Chicago Midway
Thu 8/27
5:10 pm-10:58 pm
1 stop7h 48m
$352
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-RFD
SJC-EVV
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-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 $405). Flying from San Jose, California to Illinois in June is currently the most expensive (average of $577). 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 July 26, 2026.
It’s optimal to fly from San Jose, California to Illinois in the afternoon. By choosing this option you can save up to 20% on the cost of your flight, compared to a flight at noon.
How much does it cost to fly round-trip from San Jose, California to Illinois?
Airfare is below average for this route at the moment.
San Jose, California to Illinois flights typically cost between $370 and $570 in October.The cheapest round-trip price found within the last 5 days was $318 on Frontier (Oct 1-Oct 4).
How far ahead should I book a flight from San Jose, California to Illinois?
The price you pay for your flight from San Jose, California to Illinois may vary depending on when you book. For the best chance of a lower fare, look to book 67 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated July 26, 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
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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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Find flights from San Jose to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
San Jose and Illinois flights
Browse other San Jose and Illinois flight options. Last updated on July 26, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
San Jose to Illinois flights
Consider these flights traveling from San Jose to Illinois.
Top 6 airlines flying from San Jose to Illinois
Discover the top 6 airlines that operate flights from San Jose to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$157 | Average$490 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$200 | Average$644 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$235 | Average$346 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$236 | Average$378 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$270 | Average$522 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$296 | Average$562 | FlexibilityNo cancel fee | On-time69% |