$144+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — ORD
Jun 21 — Jun 281
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 22, 2026.
Explore the most affordable flight options available from San Jose to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 22, 2026.
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 8/266:00 am
SJC
- MDW
2 stops10h 33m
Delta
Tue 9/16:00 am
MDW
- SJC
1 stop7h 33m
Delta
Deal found 5/16![Delta logo]()
$282
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/97:00 am
SJC
- ORD
2 stops12h 57m
Delta
Wed 7/16:30 am
ORD
- SJC
1 stop7h 35m
Delta
Deal found 5/17![Delta logo]()
$282
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 9/27:00 am
SJC
- MDW
2 stops12h 46m
Delta
Tue 9/86:00 am
MDW
- SJC
2 stops12h 15m
Delta
Deal found 5/16![Delta logo]()
$288
This Alaska Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:00 am
SJC
- ORD
1 stop19h 00m
Alaska Airlines
Wed 6/106:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$292
This Expedia deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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.
Sat 8/158:25 pm
SJC
- ORD
1 stop7h 52m
Multiple Airlines
Tue 8/187:59 pm
ORD
- SJC
1 stop15h 23m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$293
This Gotogate deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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.
Mon 8/178:25 pm
SJC
- ORD
1 stop7h 52m
Frontier
Wed 8/199:07 pm
ORD
- SJC
1 stop16h 55m
Frontier
Deal found 5/17![Frontier logo]()
$294
This Frontier deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/12:12 pm
SJC
- ORD
1 stop13h 16m
Frontier
Thu 8/137:15 am
ORD
- SJC
1 stop8h 02m
Frontier
Deal found 5/18![Frontier logo]()
$298
This Expedia deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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.
Sat 7/112:12 pm
SJC
- ORD
1 stop13h 16m
Multiple Airlines
Tue 7/147:59 pm
ORD
- SJC
1 stop15h 27m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 5/21. 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 7/2810:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Wed 8/58:30 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 5/21![Southwest logo]()
$302
This Frontier deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/38:25 pm
SJC
- ORD
1 stop7h 52m
Frontier
Sat 8/87:15 am
ORD
- SJC
1 stop8h 02m
Frontier
Deal found 5/18![Frontier logo]()
$303
This SmartFares deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares 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
Alaska Airlines
Tue 6/166:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$306
This Alaska Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 7/112:03 pm
SJC
- ORD
1 stop14h 57m
Alaska Airlines
Wed 7/87:59 pm
ORD
- SJC
1 stop15h 27m
Alaska Airlines
Deal found 5/17![Alaska Airlines logo]()
$307
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 22, 2026.
Discover carefully curated flight deals from San Jose to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 22, 2026.
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/239:54 am
SJC
- ORD
2 stops10h 03m
Delta
Wed 6/248:36 am
ORD
- SJC
2 stops10h 41m
Delta
Deal found 5/17![Delta logo]()
$288
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/2210:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Wed 7/18:55 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 5/20![Southwest logo]()
$332
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:00 am
SJC
- PIA
1 stop7h 54m
American Airlines
Sat 9/1912:20 pm
PIA
- SJC
2 stops11h 55m
American Airlines
Deal found 5/18![American Airlines logo]()
$354
This Alaska Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/117:13 am
SJC
- ORD
1 stop14h 23m
Alaska Airlines
Wed 7/16:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/19![Alaska Airlines logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:10 am
SJC
- RFD
1 stop9h 29m
Multiple Airlines
Sun 9/279:29 pm
RFD
- SJC
1 stop18h 00m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$436
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/94:00 pm
SJC
- ORD
1 stop6h 44m
United Airlines
Thu 7/27:55 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Deal found 5/19![United Airlines logo]()
$442
This Delta deal was found by Cheapflights users on 5/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/912:40 pm
SJC
- MLI
1 stop7h 51m
Delta
Tue 7/145:07 pm
MLI
- SJC
1 stop7h 42m
Delta
Deal found 5/21![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/107:35 pm
SJC
- MDW
1 stop7h 05m
Southwest
Tue 6/165:25 am
MDW
- SJC
2 stops8h 00m
Southwest
Deal found 5/19![Southwest logo]()
$355
This Delta deal was found by Cheapflights users on 5/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:35 am
SJC
- MLI
1 stop7h 47m
Delta
Wed 7/155:07 pm
MLI
- SJC
1 stop7h 42m
Delta
Deal found 5/21![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 5/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/512:42 pm
SJC
- PIA
2 stops9h 24m
American Airlines
Sat 9/124:43 pm
PIA
- SJC
1 stop7h 13m
American Airlines
Deal found 5/21![American Airlines logo]()
$384
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/168:55 pm
SJC
- MDW
1 stop6h 30m
Southwest
Tue 6/235:50 pm
MDW
- SJC
2 stops7h 10m
Southwest
Deal found 5/17![Southwest logo]()
$355
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 8/2112:40 pm
SJC
- MLI
1 stop7h 48m
Delta
Sat 8/296:00 am
MLI
- SJC
1 stop7h 28m
Delta
Deal found 5/17![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 7/111:10 pm
SJC
- ORD
1 stop9h 35m
United Airlines
Tue 7/147:55 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Deal found 5/16![United Airlines logo]()
$443
This Delta deal was found by Cheapflights users on 5/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/97:00 am
SJC
- MLI
2 stops13h 31m
Delta
Wed 7/155:07 pm
MLI
- SJC
1 stop7h 42m
Delta
Deal found 5/21![Delta logo]()
$354
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/282:23 pm
SJC
- BMI
1 stop6h 45m
American Airlines
Sat 8/14:30 pm
BMI
- SJC
1 stop8h 29m
American Airlines
Deal found 5/20![American Airlines logo]()
$462
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/169:54 am
SJC
- ORD
2 stops10h 03m
Delta
Sat 6/207:45 am
ORD
- SJC
1 stop6h 53m
Delta
Deal found 5/17![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 5/21. 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.
Wed 6/106:35 am
SJC
- STL
1 stop6h 45m
Southwest
Tue 6/166:10 am
STL
- SJC
2 stops7h 15m
Southwest
Deal found 5/21![Southwest logo]()
$458
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:24 pm
SJC
- PIA
2 stops11h 59m
American Airlines
Mon 6/84:47 pm
PIA
- SJC
1 stop8h 25m
American Airlines
Deal found 5/20![American Airlines logo]()
$469
This United Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/274:00 pm
SJC
- ORD
1 stop6h 44m
United Airlines
Thu 7/27:55 pm
ORD
- SJC
Nonstop4h 45m
United Airlines
Deal found 5/16![United Airlines logo]()
$517
This Delta deal was found by Cheapflights users on 5/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/99:55 am
SJC
- MLI
2 stops10h 36m
Delta
Fri 7/1711:08 am
MLI
- SJC
2 stops10h 24m
Delta
Deal found 5/21![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 7/1710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Sun 7/195:25 am
MDW
- SJC
1 stop7h 10m
Southwest
Deal found 5/16![Southwest logo]()
$459
This United Airlines deal was found by Cheapflights users on 5/21. 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.
Sat 8/2912:51 pm
SJC
- PAH
2 stops22h 19m
United Airlines
Tue 9/15:00 am
PAH
- SJC
1 stop8h 45m
United Airlines
Deal found 5/21![United Airlines logo]()
$523
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1610:00 pm
SJC
- MLI
1 stop10h 16m
Delta
Mon 6/295:17 pm
MLI
- SJC
1 stop7h 40m
Delta
Deal found 5/19![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 5/21. 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.
Thu 6/1110:20 am
SJC
- MDW
2 stops7h 35m
Southwest
Tue 6/165:30 am
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 5/21![Southwest logo]()
$466
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/247:22 pm
SJC
- PIA
2 stops11h 55m
American Airlines
Mon 7/2712:25 pm
PIA
- SJC
2 stops12h 17m
American Airlines
Deal found 5/20![American Airlines logo]()
$514
This Delta deal was found by Cheapflights users on 5/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1012:40 pm
SJC
- MLI
1 stop7h 51m
Delta
Mon 7/135:07 pm
MLI
- SJC
1 stop7h 42m
Delta
Deal found 5/21![Delta logo]()
$374
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/310:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Sun 7/55:25 am
MDW
- SJC
1 stop7h 10m
Southwest
Deal found 5/20![Southwest logo]()
$481
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:00 am
SJC
- CMI
2 stops12h 27m
American Airlines
Sun 8/302:47 pm
CMI
- SJC
1 stop9h 24m
American Airlines
Deal found 5/20![American Airlines logo]()
$533
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 7/218:55 am
SJC
- STL
2 stops7h 30m
Southwest
Sat 7/252:20 pm
STL
- SJC
1 stop6h 20m
Southwest
Deal found 5/17![Southwest logo]()
$482
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/277:22 pm
SJC
- PIA
2 stops11h 55m
American Airlines
Mon 8/34:43 pm
PIA
- SJC
1 stop8h 16m
American Airlines
Deal found 5/20![American Airlines logo]()
$553
Last-minute flights from San Jose to IllinoisDiscover last-minute flight deals from San Jose to Illinois. Data last updated May 22, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Illinois. Data last updated May 22, 2026 and is based on user searches.
This SmartFares deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares 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
Alaska Airlines
Tue 6/166:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$306
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/97:00 am
SJC
- ORD
2 stops12h 57m
Delta
Wed 7/16:30 am
ORD
- SJC
1 stop7h 35m
Delta
Deal found 5/17![Delta logo]()
$282
This Alaska Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:00 am
SJC
- ORD
1 stop19h 00m
Alaska Airlines
Wed 6/106:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$292
This CheapOair deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:00 am
SJC
- ORD
1 stop19h 00m
Alaska Airlines
Mon 6/157:59 pm
ORD
- SJC
1 stop15h 27m
Alaska Airlines
Deal found 5/19![Alaska Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/98:55 pm
SJC
- MDW
1 stop6h 30m
Southwest
Tue 6/165:30 am
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 5/17![Southwest logo]()
$322
This CheapOair deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:00 am
SJC
- ORD
1 stop19h 00m
Alaska Airlines
Sat 6/275:59 pm
ORD
- SJC
1 stop7h 55m
Alaska Airlines
Deal found 5/17![Alaska Airlines logo]()
$337
This CheapOair deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1012:03 pm
SJC
- ORD
1 stop14h 57m
Alaska Airlines
Tue 6/167:59 pm
ORD
- SJC
1 stop15h 27m
Alaska Airlines
Deal found 5/21![Alaska Airlines logo]()
$322
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/2210:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Wed 7/18:55 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 5/20![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 5/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2312:46 pm
SJC
- ORD
1 stop9h 13m
Delta
Wed 6/242:09 pm
ORD
- SJC
1 stop6h 21m
Delta
Deal found 5/21![Delta logo]()
$338
This Frontier deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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.
Sat 6/272:12 pm
SJC
- ORD
1 stop12h 55m
Frontier
Thu 7/27:20 am
ORD
- SJC
1 stop7h 57m
Frontier
Deal found 5/16![Frontier logo]()
$329
This Alaska Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/303:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
Wed 7/156:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$307
This Alaska Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/303:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
Thu 7/166:20 am
ORD
- SJC
1 stop7h 04m
Alaska Airlines
Deal found 5/18![Alaska Airlines 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 May 22, 2026.
Search for one-way flight options from San Jose to Illinois. Find affordable one-way fares based on user searches. Data last updated May 22, 2026.
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/98:19 pm
SJC
- MDW
2 stops10h 18m
Delta
Deal found 5/16![Delta logo]()
$144
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:00 am
SJC
- ORD
2 stops12h 57m
Delta
Deal found 5/18![Delta logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/18:25 pm
SJC
- ORD
1 stop7h 52m
Frontier
Deal found 5/18![Frontier logo]()
$147
This Expedia deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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.
Sat 7/48:25 pm
SJC
- ORD
1 stop7h 54m
Frontier
Deal found 5/17![Frontier logo]()
$149
This Alaska Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/163:15 pm
SJC
- ORD
1 stop6h 21m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$154
This CheapOair deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 7/38:25 pm
SJC
- ORD
1 stop7h 54m
Frontier
Deal found 5/17![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:03 pm
SJC
- STL
2 stops20h 12m
Frontier
Deal found 5/20![Frontier logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/68:23 pm
SJC
- ORD
2 stops31h 14m
Frontier
Deal found 5/20![Frontier logo]()
$156
This CheapOair deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:02 pm
SJC
- ORD
1 stop18h 19m
Alaska Airlines
Deal found 5/19![Alaska Airlines logo]()
$159
This Expedia deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/292:12 pm
SJC
- ORD
1 stop12h 55m
Frontier
Deal found 5/18![Frontier logo]()
$160
This Expedia deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/92:12 pm
SJC
- ORD
1 stop13h 16m
Frontier
Deal found 5/18![Frontier logo]()
$161
This United Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/242:32 pm
SJC
- ORD
1 stop8h 12m
United Airlines
Deal found 5/17![United Airlines logo]()
$163
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 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $282 (Delta) |
One-way from | $144 (Delta) |
Popular in | March |
Cheapest in | February |
Average price | $486 |
Good round-trip deal | $471 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 22, 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
Tue 6/23
9:54 am-9:57 pm
2 stops10h 03m
Chicago O'Hare Intl
Wed 6/24
8:36 am-5:17 pm
2 stops10h 41m
$288
Quickest round-trip
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Mon 6/22
10:55 pm-5:00 am
Nonstop4h 05m
Chicago Midway
Wed 7/1
8:55 pm-11:25 pm
Nonstop4h 30m
$332
San JoseMoline
SJC - MLI
SJCMLI
San Jose
Thu 7/9
12:40 pm-10:31 pm
1 stop7h 51m
Moline Quad-City
Tue 7/14
5:07 pm-10:49 pm
1 stop7h 42m
$349
San JoseMoline
SJC - MLI
SJCMLI
San Jose
Wed 7/8
6:35 am-4:22 pm
1 stop7h 47m
Moline Quad-City
Wed 7/15
5:07 pm-10:49 pm
1 stop7h 42m
$349
San JoseMoline
SJC - MLI
SJCMLI
San Jose
Fri 8/21
12:40 pm-10:28 pm
1 stop7h 48m
Moline Quad-City
Sat 8/29
6:00 am-11:28 am
1 stop7h 28m
$349
San JosePeoria
SJC - PIA
SJCPIA
San Jose
Sat 9/12
6:00 am-3:54 pm
1 stop7h 54m
Greater Peoria
Sat 9/19
12:20 pm-10:15 pm
2 stops11h 55m
$354
San JoseMoline
SJC - MLI
SJCMLI
San Jose
Thu 7/9
7:00 am-10:31 pm
2 stops13h 31m
Moline Quad-City
Wed 7/15
5:07 pm-10:49 pm
1 stop7h 42m
$354
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 6/10
7:35 pm-4:40 am
1 stop7h 05m
Chicago Midway
Tue 6/16
5:25 am-11:25 am
2 stops8h 00m
$355
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 6/16
8:55 pm-5:25 am
1 stop6h 30m
Chicago Midway
Tue 6/23
5:50 pm-11:00 pm
2 stops7h 10m
$355
San JoseChicago
SJC - ORD
SJCORD
San Jose
Tue 6/16
9:54 am-9:57 pm
2 stops10h 03m
Chicago O'Hare Intl
Sat 6/20
7:45 am-12:38 pm
1 stop6h 53m
$357
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from San Jose to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from San Jose with our price prediction graph.
SJC-ORD
SJC-MDW
SJC-RFD
SJC-STL
SJC-PIA
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-RFD
SJC-STL
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 April is currently the most expensive (average of $265). 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 22, 2026.
It’s optimal to fly from San Jose, California to Illinois at noon. By choosing this option you can save up to 18% 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?
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.
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 22, 2026.
Read through reviews of airlines operating flights from San Jose to Illinois, such as Alaska Airlines,Southwest, andDelta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
7.9
Comfort
7.8
Entertainment
7.0
Food
7.0
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Overall
7.9
Comfort
7.8
Entertainment
7.0
Food
7.0
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Overall
7.9
Comfort
7.8
Entertainment
7.0
Food
7.0
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Overall
7.9
Comfort
7.8
Entertainment
7.0
Food
7.0
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Overall
7.9
Comfort
7.8
Entertainment
7.0
Food
7.0
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Overall
7.9
Comfort
7.8
Entertainment
7.0
Food
7.0
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Related info for your journey
Find useful and relevant information for your journey from San Jose to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for San Jose to Illinois
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Complete your trip
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Search flights from San Jose to Illinois by cabin class
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 May 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
San Jose to Illinois flights
Consider these flights traveling from San Jose to Illinois.
Top 7 airlines flying from San Jose to Illinois
Discover the top 7 airlines that operate flights from San Jose to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 22, 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$339 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$236 | Average$378 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$270 | Average$517 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$278 | Average$554 | FlexibilityNo cancel fee | On-time69% |