$125+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — ORD
Jun 9 — Jun 161
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 May 10, 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 May 10, 2026.
This Frontier deal was found by Cheapflights users on 5/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:21 am
SJC
- STL
1 stop10h 05m
Frontier
Wed 6/36:51 pm
STL
- SJC
1 stop20h 26m
Frontier
Deal found 5/7![Frontier logo]()
$232
This Gotogate deal was found by Cheapflights users on 5/8. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/72:12 pm
SJC
- STL
1 stop27h 59m
Frontier
Sun 8/22:52 pm
STL
- SJC
1 stop24h 25m
Frontier
Deal found 5/8![Frontier logo]()
$259
This CheapOair deal was found by Cheapflights users on 5/6. 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.
Mon 5/252:12 pm
SJC
- STL
1 stop25h 54m
Frontier
Fri 5/299:06 pm
STL
- SJC
1 stop18h 11m
Frontier
Deal found 5/6![Frontier logo]()
$270
This Expedia deal was found by Cheapflights users on 5/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:03 am
SJC
- ORD
1 stop6h 54m
Multiple Airlines
Mon 8/177:15 am
ORD
- SJC
1 stop8h 02m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$273
This CheapOair deal was found by Cheapflights users on 5/9. 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.
Mon 6/12:12 pm
SJC
- STL
1 stop25h 54m
Frontier
Thu 6/49:06 pm
STL
- SJC
1 stop18h 11m
Frontier
Deal found 5/9![Frontier logo]()
$274
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/102:10 pm
SJC
- MDW
1 stop7h 40m
Southwest
Tue 6/235:30 am
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 5/5![Southwest logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 6/21:14 pm
SJC
- ORD
1 stop7h 45m
Alaska Airlines
Wed 6/32:10 pm
ORD
- SJC
1 stop7h 12m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$277
This CheapOair deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/52:12 pm
SJC
- STL
1 stop25h 22m
Frontier
Sun 6/142:56 pm
STL
- SJC
1 stop24h 21m
Frontier
Deal found 5/5![Frontier logo]()
$280
This CheapOair deal was found by Cheapflights users on 5/8. 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.
Sat 5/2312:57 pm
SJC
- ORD
1 stop15h 37m
Frontier
Wed 5/278:46 pm
ORD
- SJC
1 stop17h 13m
Frontier
Deal found 5/8![Frontier logo]()
$280
This Mytrip deal was found by Cheapflights users on 5/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:57 pm
SJC
- ORD
1 stop15h 22m
Frontier
Sun 8/309:07 pm
ORD
- SJC
1 stop16h 55m
Frontier
Deal found 5/7![Frontier logo]()
$281
This Southwest deal was found by Cheapflights users on 5/8. 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.
Tue 6/21:45 pm
SJC
- MDW
1 stop6h 15m
Southwest
Wed 6/35:30 pm
MDW
- SJC
2 stops7h 30m
Southwest
Deal found 5/8![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 5/8. 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.
Tue 6/212:45 pm
SJC
- ORD
2 stops8h 10m
Southwest
Wed 6/34:50 pm
ORD
- SJC
1 stop7h 25m
Southwest
Deal found 5/8![Southwest logo]()
$282
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 May 10, 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 May 10, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:29 am
SJC
- ORD
1 stop8h 34m
Alaska Airlines
Tue 8/256:01 am
ORD
- SJC
1 stop9h 44m
Alaska Airlines
Deal found 5/8![Alaska Airlines logo]()
$312
This American Airlines deal was found by Cheapflights users on 5/7. 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 5/272:34 pm
SJC
- MLI
1 stop6h 56m
American Airlines
Sat 5/304:42 pm
MLI
- SJC
1 stop8h 31m
American Airlines
Deal found 5/7![American Airlines logo]()
$349
This Southwest deal was found by Cheapflights users on 5/8. 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.
Wed 6/247:35 pm
SJC
- MDW
1 stop7h 05m
Southwest
Mon 6/298:50 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 5/8![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 5/9. 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 5/277:10 am
SJC
- MLI
1 stop7h 27m
Delta
Sat 5/305:56 am
MLI
- SJC
2 stops13h 06m
Delta
Deal found 5/9![Delta logo]()
$394
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/412:57 pm
SJC
- RFD
2 stops29h 23m
Multiple Airlines
Sun 6/141:13 pm
RFD
- SJC
1 stop26h 04m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$413
This United Airlines deal was found by Cheapflights users on 5/6. 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.
Fri 8/212:09 pm
SJC
- ORD
Nonstop4h 23m
United Airlines
Tue 9/18:40 am
ORD
- SJC
Nonstop4h 45m
United Airlines
Deal found 5/6![United Airlines logo]()
$432
This Alaska Airlines deal was found by Cheapflights users on 5/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/282:25 pm
SJC
- ORD
1 stop7h 32m
Alaska Airlines
Thu 10/19:00 am
ORD
- SJC
1 stop8h 51m
Alaska Airlines
Deal found 5/8![Alaska Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/210:00 pm
SJC
- STL
1 stop8h 18m
Delta
Tue 6/92:28 pm
STL
- SJC
1 stop6h 02m
Delta
Deal found 5/5![Delta logo]()
$397
This Southwest deal was found by Cheapflights users on 5/7. 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.
Mon 7/2010:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Sat 7/258:25 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 5/7![Southwest logo]()
$407
This Alaska Airlines deal was found by Cheapflights users on 5/9. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:06 am
SJC
- ORD
1 stop9h 44m
Alaska Airlines
Mon 6/157:59 pm
ORD
- SJC
1 stop15h 27m
Alaska Airlines
Deal found 5/9![Alaska Airlines logo]()
$388
This American Airlines deal was found by Cheapflights users on 5/7. 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.
Thu 5/286:00 am
SJC
- PIA
1 stop7h 50m
American Airlines
Mon 6/14:46 pm
PIA
- SJC
1 stop8h 27m
American Airlines
Deal found 5/7![American Airlines logo]()
$449
This United Airlines deal was found by Cheapflights users on 5/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/202:32 pm
SJC
- ORD
1 stop8h 12m
United Airlines
Sat 7/257:55 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Deal found 5/7![United Airlines logo]()
$455
This Delta deal was found by Cheapflights users on 5/6. 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.
Thu 8/66:30 am
SJC
- MLI
1 stop7h 55m
Delta
Tue 8/116:00 am
MLI
- SJC
1 stop7h 28m
Delta
Deal found 5/6![Delta logo]()
$419
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/1010:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 6/168:55 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 5/5![Southwest logo]()
$425
This American Airlines deal was found by Cheapflights users on 5/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:34 pm
SJC
- MLI
1 stop6h 56m
American Airlines
Wed 6/1011:09 am
MLI
- SJC
2 stops9h 27m
American Airlines
Deal found 5/6![American Airlines logo]()
$452
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/62:05 pm
SJC
- MDW
1 stop5h 50m
Southwest
Sun 6/75:25 am
MDW
- SJC
1 stop7h 10m
Southwest
Deal found 5/5![Southwest logo]()
$427
This Delta deal was found by Cheapflights users on 5/9. 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.
Mon 6/81:15 pm
SJC
- MDW
1 stop21h 54m
Delta
Tue 6/161:49 pm
MDW
- SJC
1 stop8h 50m
Delta
Deal found 5/9![Delta logo]()
$431
This United Airlines deal was found by Cheapflights users on 5/6. 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.
Wed 9/306:40 am
SJC
- ORD
Nonstop4h 20m
United Airlines
Thu 10/18:00 pm
ORD
- SJC
Nonstop4h 36m
United Airlines
Deal found 5/6![United Airlines logo]()
$477
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/192:12 pm
SJC
- RFD
2 stops20h 02m
Multiple Airlines
Sun 6/211:13 pm
RFD
- SJC
1 stop26h 04m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$537
This Alaska Airlines deal was found by Cheapflights users on 5/9. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:06 am
SJC
- STL
2 stops14h 48m
Alaska Airlines
Sat 6/135:37 pm
STL
- SJC
1 stop7h 44m
Alaska Airlines
Deal found 5/9![Alaska Airlines logo]()
$445
This Southwest deal was found by Cheapflights users on 5/8. 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 6/115:00 pm
SJC
- MDW
1 stop6h 25m
Southwest
Tue 6/168:55 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 5/8![Southwest logo]()
$437
This Delta deal was found by Cheapflights users on 5/7. 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.
Sat 9/261:35 pm
SJC
- ORD
1 stop6h 23m
Delta
Sun 9/277:35 am
ORD
- SJC
1 stop7h 18m
Delta
Deal found 5/7![Delta logo]()
$437
This Alaska Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/198:15 pm
SJC
- ORD
1 stop8h 05m
Alaska Airlines
Wed 5/209:00 am
ORD
- SJC
1 stop7h 13m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$451
This American Airlines deal was found by Cheapflights users on 5/7. 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.
Sat 5/232:34 pm
SJC
- PIA
1 stop6h 59m
American Airlines
Wed 5/274:46 pm
PIA
- SJC
1 stop8h 27m
American Airlines
Deal found 5/7![American Airlines logo]()
$519
This Southwest deal was found by Cheapflights users on 5/9. 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 7/302:35 pm
SJC
- MDW
1 stop7h 35m
Southwest
Sat 8/86:25 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 5/9![Southwest logo]()
$437
This Delta deal was found by Cheapflights users on 5/9. 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.
Thu 9/177:00 am
SJC
- ORD
1 stop8h 30m
Delta
Mon 9/211:55 pm
ORD
- SJC
2 stops9h 50m
Delta
Deal found 5/9![Delta logo]()
$440
This Alaska Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/210:22 am
SJC
- STL
2 stops11h 32m
Alaska Airlines
Mon 6/87:41 pm
STL
- SJC
1 stop26h 19m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$473
This Delta deal was found by Cheapflights users on 5/9. 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.
Tue 6/306:00 am
SJC
- ORD
2 stops8h 26m
Delta
Mon 7/67:45 am
ORD
- SJC
1 stop6h 53m
Delta
Deal found 5/9![Delta logo]()
$440
This Southwest deal was found by Cheapflights users on 5/7. 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.
Thu 5/281:00 pm
SJC
- STL
2 stops7h 40m
Southwest
Wed 6/35:40 pm
STL
- SJC
2 stops7h 20m
Southwest
Deal found 5/7![Southwest logo]()
$441
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/2712:38 pm
SJC
- PIA
2 stops9h 21m
American Airlines
Wed 6/34:46 pm
PIA
- SJC
1 stop8h 27m
American Airlines
Deal found 5/5![American Airlines logo]()
$534
Last-minute flights from San Jose to IllinoisDiscover last-minute flight deals from San Jose to Illinois. Data last updated May 10, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Illinois. Data last updated May 10, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 5/8. 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.
Sat 5/2312:57 pm
SJC
- ORD
1 stop15h 37m
Frontier
Wed 5/278:46 pm
ORD
- SJC
1 stop17h 13m
Frontier
Deal found 5/8![Frontier logo]()
$280
This CheapOair deal was found by Cheapflights users on 5/6. 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.
Mon 5/252:12 pm
SJC
- STL
1 stop25h 54m
Frontier
Fri 5/299:06 pm
STL
- SJC
1 stop18h 11m
Frontier
Deal found 5/6![Frontier logo]()
$270
This Frontier deal was found by Cheapflights users on 5/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:21 am
SJC
- STL
1 stop10h 05m
Frontier
Wed 6/36:51 pm
STL
- SJC
1 stop20h 26m
Frontier
Deal found 5/7![Frontier logo]()
$232
This CheapOair deal was found by Cheapflights users on 5/9. 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.
Mon 6/12:12 pm
SJC
- STL
1 stop25h 54m
Frontier
Thu 6/49:06 pm
STL
- SJC
1 stop18h 11m
Frontier
Deal found 5/9![Frontier logo]()
$274
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 6/21:14 pm
SJC
- ORD
1 stop7h 45m
Alaska Airlines
Wed 6/32:10 pm
ORD
- SJC
1 stop7h 12m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 5/8. 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.
Tue 6/21:45 pm
SJC
- MDW
1 stop6h 15m
Southwest
Wed 6/35:30 pm
MDW
- SJC
2 stops7h 30m
Southwest
Deal found 5/8![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 5/8. 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.
Tue 6/212:45 pm
SJC
- ORD
2 stops8h 10m
Southwest
Wed 6/34:50 pm
ORD
- SJC
1 stop7h 25m
Southwest
Deal found 5/8![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 5/6. 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.
Tue 6/29:45 am
SJC
- MDW
2 stops7h 45m
Southwest
Tue 6/95:25 am
MDW
- SJC
2 stops8h 00m
Southwest
Deal found 5/6![Southwest logo]()
$287
This CheapOair deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/52:12 pm
SJC
- STL
1 stop25h 22m
Frontier
Sun 6/142:56 pm
STL
- SJC
1 stop24h 21m
Frontier
Deal found 5/5![Frontier logo]()
$280
This Gotogate deal was found by Cheapflights users on 5/8. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/72:12 pm
SJC
- STL
1 stop27h 59m
Frontier
Sun 8/22:52 pm
STL
- SJC
1 stop24h 25m
Frontier
Deal found 5/8![Frontier logo]()
$259
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/102:10 pm
SJC
- MDW
1 stop7h 40m
Southwest
Tue 6/235:30 am
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 5/5![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 5/10. 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.
Wed 6/106:20 am
SJC
- MDW
2 stops10h 11m
Delta
Tue 6/161:26 pm
MDW
- SJC
2 stops9h 13m
Delta
Deal found 5/10![Delta logo]()
$288
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 May 10, 2026.
Search for one-way flight options from San Jose to Illinois. Find affordable one-way fares based on user searches. Data last updated May 10, 2026.
This Priceline deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:21 am
SJC
- STL
1 stop10h 05m
Frontier
Deal found 5/5![Frontier logo]()
$125
This CheapOair deal was found by Cheapflights users on 5/6. 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.
Mon 6/82:12 pm
SJC
- STL
1 stop24h 53m
Frontier
Deal found 5/6![Frontier logo]()
$130
This CheapOair deal was found by Cheapflights users on 5/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/262:12 pm
SJC
- STL
1 stop21h 55m
Frontier
Deal found 5/7![Frontier logo]()
$131
This Booking.com deal was found by Cheapflights users on 5/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/72:12 pm
SJC
- STL
1 stop27h 59m
Frontier
Deal found 5/8![Frontier logo]()
$136
This Delta deal was found by Cheapflights users on 5/6. 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 6/210:00 pm
SJC
- MDW
1 stop10h 00m
Delta
Deal found 5/6![Delta logo]()
$144
This Southwest deal was found by Cheapflights users on 5/8. 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.
Tue 6/212:45 pm
SJC
- ORD
2 stops9h 10m
Southwest
Deal found 5/8![Southwest logo]()
$144
This Frontier deal was found by Cheapflights users on 5/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/178:25 pm
SJC
- ORD
1 stop7h 52m
Frontier
Deal found 5/9![Frontier logo]()
$145
This Delta deal was found by Cheapflights users on 5/7. 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 6/25:45 pm
SJC
- ORD
2 stops12h 51m
Delta
Deal found 5/7![Delta logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/112:57 pm
SJC
- ORD
2 stops29h 35m
Frontier
Deal found 5/5![Frontier logo]()
$150
This Frontier deal was found by Cheapflights users on 5/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/152:12 pm
SJC
- ORD
1 stop12h 55m
Frontier
Deal found 5/6![Frontier logo]()
$151
This Booking.com deal was found by Cheapflights users on 5/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/3112:57 pm
SJC
- ORD
1 stop15h 37m
Frontier
Deal found 5/9![Frontier logo]()
$152
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 6/163:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$154
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 May 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $232 (Frontier) |
One-way from | $125 (Priceline) |
Popular in | March |
Cheapest in | February |
Average price | $479 |
Good round-trip deal | $448 or less |
Good one-way deal | $203 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 May 10, 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
Thu 8/20
8:29 am-7:03 pm
1 stop8h 34m
Chicago O'Hare Intl
Tue 8/25
6:01 am-1:45 pm
1 stop9h 44m
$312
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
$349
San JoseChicago
SJC - ORD
SJCORD
San Jose
Mon 9/28
2:25 pm-11:57 pm
1 stop7h 32m
Chicago O'Hare Intl
Thu 10/1
9:00 am-3:51 pm
1 stop8h 51m
$357
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 6/24
7:35 pm-4:40 am
1 stop7h 05m
Chicago Midway
Mon 6/29
8:50 pm-11:25 pm
Nonstop4h 35m
$387
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 6/9
7:06 am-6:50 pm
1 stop9h 44m
Chicago O'Hare Intl
Mon 6/15
7:59 pm-9:26 am
1 stop15h 27m
$388
San JoseMoline
SJC - MLI
SJCMLI
San Jose
Wed 5/27
7:10 am-4:37 pm
1 stop7h 27m
Moline Quad-City
Sat 5/30
5:56 am-5:02 pm
2 stops13h 06m
$394
San JoseSt. Louis
SJC - STL
SJCSTL
San Jose
Tue 6/2
10:00 pm-8:18 am
1 stop8h 18m
Lambert-St Louis
Tue 6/9
2:28 pm-6:30 pm
1 stop6h 02m
$397
Quickest round-trip
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Mon 7/20
10:55 pm-5:00 am
Nonstop4h 05m
Chicago Midway
Sat 7/25
8:25 pm-10:55 pm
Nonstop4h 30m
$407
San JoseChicago
SJC - RFD
SJCRFD
San Jose
Thu 6/4
12:57 pm-8:20 pm
2 stops29h 23m
Chicago Greater Rockford
Sun 6/14
1:13 pm-1:17 pm
1 stop26h 04m
$413
San JoseMoline
SJC - MLI
SJCMLI
San Jose
Thu 8/6
6:30 am-4:25 pm
1 stop7h 55m
Moline Quad-City
Tue 8/11
6:00 am-11:28 am
1 stop7h 28m
$419
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from San Jose to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from San Jose with our price prediction graph.
SJC-ORD
SJC-MDW
SJC-STL
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-ORD
SJC-MDW
SJC-STL
SJC-RFD
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 88 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from San Jose, California to Illinois?
Currently, March is the cheapest month in which you can book a flight from San Jose, California to Illinois (average of $95). Flying from San Jose, California to Illinois in December is currently the most expensive (average of $258). 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 May 10, 2026.
It’s optimal to fly from San Jose, California to Illinois at noon. By choosing this option you can save up to 12% 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 May 10, 2026.
Read through reviews of airlines operating flights from San Jose to Illinois, such as Southwest,Alaska Airlines, andDelta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
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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San Jose and Illinois flights
Browse other San Jose and Illinois flight options. Last updated on May 10, 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 May 10, 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$200 | Average$627 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$235 | Average$334 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$236 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$270 | Average$516 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$278 | Average$548 | FlexibilityNo cancel fee | On-time69% |