$135+ Cheap flights from Illinois to San José (SJO)
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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJO
jul. 12 — jul. 191
Round-trip
1 adult, Economy
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Cheapest flights from Illinois to San JoséExplore the most affordable flight options available from Illinois to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on junio 12, 2026.
Explore the most affordable flight options available from Illinois to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on junio 12, 2026.
This Delta deal was found by Cheapflights users on 6/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/306:00 am
STL
- SJO
1 stop6h 49m
Delta
jue. 9/31:14 pm
SJO
- STL
1 stop9h 44m
Delta
Deal found 6/8![Delta logo]()
$400
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/95:00 am
STL
- SJO
1 stop16h 07m
American Airlines
jue. 9/172:57 pm
SJO
- STL
2 stops17h 32m
American Airlines
Deal found 6/9![American Airlines logo]()
$405
This JetBlue deal was found by Cheapflights users on 6/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/217:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
mié. 9/22:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 6/7![JetBlue logo]()
$460
This Southwest deal was found by Cheapflights users on 6/9. 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.
lun. 10/58:20 pm
MDW
- SJO
1 stop10h 40m
Southwest
vie. 10/1612:55 pm
SJO
- MDW
1 stop15h 45m
Southwest
Deal found 6/9![Southwest logo]()
$462
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/87:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
vie. 9/181:05 pm
SJO
- ORD
1 stop9h 26m
JetBlue
Deal found 6/10![JetBlue logo]()
$465
This Southwest deal was found by Cheapflights users on 6/8. 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.
lun. 10/265:05 am
MDW
- SJO
1 stop7h 55m
Southwest
vie. 10/301:30 pm
SJO
- MDW
2 stops10h 15m
Southwest
Deal found 6/8![Southwest logo]()
$466
This Delta deal was found by Cheapflights users on 6/10. 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.
jue. 8/276:00 am
STL
- SJO
1 stop6h 49m
Delta
jue. 9/31:14 pm
SJO
- STL
1 stop9h 44m
Delta
Deal found 6/10![Delta logo]()
$469
This Southwest deal was found by Cheapflights users on 6/8. 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.
sáb. 8/295:00 am
MDW
- SJO
1 stop8h 15m
Southwest
sáb. 9/59:30 am
SJO
- MDW
1 stop10h 25m
Southwest
Deal found 6/8![Southwest logo]()
$469
This Faresmojo deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/77:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
jue. 8/132:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 6/11![JetBlue logo]()
$469
This JetBlue deal was found by Cheapflights users on 6/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/87:00 am
ORD
- SJO
1 stop6h 59m
JetBlue
vie. 11/133:05 pm
SJO
- ORD
1 stop8h 39m
JetBlue
Deal found 6/8![JetBlue logo]()
$470
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/1610:10 am
MDW
- SJO
2 stops9h 30m
Southwest
sáb. 9/269:30 am
SJO
- MDW
2 stops9h 50m
Southwest
Deal found 6/11![Southwest logo]()
$471
This Southwest deal was found by Cheapflights users on 6/8. 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.
lun. 8/247:55 am
MDW
- SJO
2 stops11h 45m
Southwest
mar. 9/19:00 am
SJO
- MDW
2 stops12h 20m
Southwest
Deal found 6/8![Southwest logo]()
$473
Best flights from Illinois to San JoséDiscover carefully curated flight deals from Illinois to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated junio 12, 2026.
Discover carefully curated flight deals from Illinois to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated junio 12, 2026.
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/1910:25 am
MDW
- SJO
1 stop8h 35m
Southwest
mié. 9/231:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Deal found 6/10![Southwest logo]()
$462
This Volaris deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/81:49 pm
ORD
- SJO
1 stop11h 10m
Multiple Airlines
dom. 10/114:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$481
This Copa Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/168:02 am
ORD
- SJO
1 stop25h 17m
Copa Airlines
mié. 8/198:45 am
SJO
- ORD
1 stop15h 17m
Copa Airlines
Deal found 6/11![Copa Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 6/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/316:05 am
MDW
- SJO
1 stop6h 44m
Delta
lun. 9/71:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Deal found 6/8![Delta logo]()
$502
This United Airlines deal was found by Cheapflights users on 6/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/268:50 am
STL
- SJO
1 stop11h 49m
United Airlines
mié. 10/2810:28 pm
SJO
- STL
1 stop17h 12m
United Airlines
Deal found 6/9![United Airlines logo]()
$520
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/1610:10 am
MDW
- SJO
2 stops9h 30m
Southwest
sáb. 9/269:30 am
SJO
- MDW
2 stops9h 50m
Southwest
Deal found 6/11![Southwest logo]()
$471
This Copa Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/308:01 am
ORD
- SJO
1 stop11h 58m
Copa Airlines
dom. 10/45:45 am
SJO
- ORD
1 stop18h 12m
Copa Airlines
Deal found 6/11![Copa Airlines logo]()
$490
This Copa Airlines deal was found by Cheapflights users on 6/7. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/43:21 pm
ORD
- SJO
1 stop17h 58m
Copa Airlines
lun. 8/104:08 am
SJO
- ORD
1 stop19h 54m
Copa Airlines
Deal found 6/7![Copa Airlines logo]()
$490
This United Airlines deal was found by Cheapflights users on 6/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/12:26 pm
MLI
- SJO
2 stops20h 59m
United Airlines
jue. 11/52:20 pm
SJO
- MLI
2 stops24h 45m
United Airlines
Deal found 6/9![United Airlines logo]()
$543
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/306:15 am
MDW
- SJO
1 stop7h 30m
Southwest
dom. 10/41:35 pm
SJO
- MDW
1 stop15h 05m
Southwest
Deal found 6/11![Southwest logo]()
$497
This Delta deal was found by Cheapflights users on 6/7. 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.
dom. 8/306:00 am
STL
- SJO
1 stop6h 49m
Delta
jue. 9/31:14 pm
SJO
- STL
1 stop9h 44m
Delta
Deal found 6/7![Delta logo]()
$552
This Copa Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/233:20 pm
ORD
- SJO
1 stop18h 44m
Copa Airlines
vie. 10/3010:26 am
SJO
- ORD
1 stop13h 39m
Copa Airlines
Deal found 6/11![Copa Airlines logo]()
$490
This KAYAK deal was found by Cheapflights users on 6/9. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/218:13 pm
BMI
- SJO
2 stops26h 46m
GOL
sáb. 11/286:22 am
SJO
- BMI
1 stop15h 14m
GOL
Deal found 6/9![GOL logo]()
$1,193
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/196:15 am
STL
- SJO
1 stop7h 06m
United Airlines
vie. 10/231:25 pm
SJO
- STL
1 stop8h 05m
United Airlines
Deal found 6/8![United Airlines logo]()
$552
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/116:00 pm
BMI
- SJO
2 stops20h 00m
American Airlines
sáb. 7/1811:41 pm
SJO
- BMI
1 stop22h 27m
American Airlines
Deal found 6/11![American Airlines logo]()
$1,236
This Southwest deal was found by Cheapflights users on 6/7. 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.
dom. 10/49:55 pm
MDW
- SJO
2 stops15h 40m
Southwest
mié. 10/71:00 pm
SJO
- MDW
1 stop9h 00m
Southwest
Deal found 6/7![Southwest logo]()
$511
This Delta deal was found by Cheapflights users on 6/7. 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.
vie. 11/131:30 pm
STL
- SJO
1 stop8h 45m
Delta
dom. 11/227:00 am
SJO
- STL
1 stop8h 58m
Delta
Deal found 6/7![Delta logo]()
$592
This Copa Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/18:02 am
ORD
- SJO
1 stop24h 08m
Copa Airlines
vie. 8/74:08 am
SJO
- ORD
1 stop19h 54m
Copa Airlines
Deal found 6/11![Copa Airlines logo]()
$490
This Copa Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/223:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
dom. 7/265:45 am
SJO
- ORD
1 stop21h 15m
Copa Airlines
Deal found 6/11![Copa Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 6/9. 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.
mar. 12/86:00 am
MDW
- SJO
1 stop7h 05m
Delta
mar. 12/227:00 am
SJO
- MDW
1 stop9h 25m
Delta
Deal found 6/9![Delta logo]()
$611
This Southwest deal was found by Cheapflights users on 6/7. 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.
dom. 8/308:20 am
STL
- SJO
2 stops11h 20m
Southwest
jue. 9/31:40 pm
SJO
- STL
1 stop7h 10m
Southwest
Deal found 6/7![Southwest logo]()
$559
This Copa Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 7/273:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
mié. 8/510:03 am
SJO
- ORD
1 stop26h 56m
Copa Airlines
Deal found 6/11![Copa Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 6/10. 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.
mié. 10/286:00 am
MDW
- SJO
1 stop6h 58m
Delta
jue. 11/52:23 pm
SJO
- MDW
1 stop7h 47m
Delta
Deal found 6/10![Delta logo]()
$611
This Copa Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/213:20 pm
ORD
- SJO
1 stop20h 38m
Copa Airlines
dom. 10/2510:26 am
SJO
- ORD
1 stop26h 20m
Copa Airlines
Deal found 6/11![Copa Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 6/9. 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.
mié. 12/26:00 am
MDW
- SJO
1 stop16h 15m
Delta
lun. 12/72:30 pm
SJO
- MDW
1 stop7h 40m
Delta
Deal found 6/9![Delta logo]()
$611
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 7/276:30 pm
MLI
- SJO
2 stops18h 51m
United Airlines
lun. 8/37:55 am
SJO
- MLI
2 stops29h 01m
United Airlines
Deal found 6/12![United Airlines logo]()
$777
This Copa Airlines deal was found by Cheapflights users on 6/7. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 7/273:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
sáb. 8/14:08 am
SJO
- ORD
1 stop19h 54m
Copa Airlines
Deal found 6/7![Copa Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 6/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/276:00 am
MDW
- SJO
1 stop6h 58m
Delta
dom. 11/12:23 pm
SJO
- MDW
1 stop7h 47m
Delta
Deal found 6/8![Delta logo]()
$611
This Copa Airlines deal was found by Cheapflights users on 6/7. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 7/53:21 pm
ORD
- SJO
1 stop18h 00m
Copa Airlines
dom. 7/128:30 am
SJO
- ORD
1 stop18h 30m
Copa Airlines
Deal found 6/7![Copa Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 6/9. 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.
mar. 11/246:00 am
MDW
- SJO
1 stop16h 15m
Delta
jue. 11/267:00 am
SJO
- MDW
1 stop15h 10m
Delta
Deal found 6/9![Delta logo]()
$611
Last-minute flights from Illinois to San JoséDiscover last-minute flight deals from Illinois to San José. Data last updated junio 12, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to San José. Data last updated junio 12, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 6/10. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/139:20 pm
ORD
- SJO
2 stops24h 15m
Air Canada
lun. 6/157:15 am
SJO
- ORD
1 stop26h 03m
Air Canada
Deal found 6/10![Air Canada logo]()
$507
This Air Canada deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/139:55 am
ORD
- SJO
1 stop13h 05m
Air Canada
mar. 6/237:10 am
SJO
- ORD
2 stops23h 40m
Air Canada
Deal found 6/11![Air Canada logo]()
$511
This Air Canada deal was found by Cheapflights users on 6/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 6/146:22 pm
ORD
- SJO
2 stops28h 38m
Air Canada
mar. 6/307:10 am
SJO
- ORD
1 stop11h 37m
Air Canada
Deal found 6/9![Air Canada logo]()
$508
This Air Canada deal was found by Cheapflights users on 6/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/176:22 pm
ORD
- SJO
2 stops28h 38m
Air Canada
mar. 6/237:10 am
SJO
- ORD
2 stops23h 40m
Air Canada
Deal found 6/9![Air Canada logo]()
$516
This Air Canada deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/186:22 pm
ORD
- SJO
2 stops26h 58m
Air Canada
lun. 6/227:15 am
SJO
- ORD
2 stops23h 30m
Air Canada
Deal found 6/12![Air Canada logo]()
$503
This Copa Airlines deal was found by Cheapflights users on 6/8. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/71:20 am
ORD
- SJO
1 stop10h 46m
Copa Airlines
mar. 7/141:37 pm
SJO
- ORD
1 stop13h 23m
Copa Airlines
Deal found 6/8![Copa Airlines logo]()
$505
This Copa Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/108:02 am
ORD
- SJO
1 stop24h 10m
Copa Airlines
sáb. 7/188:45 am
SJO
- ORD
1 stop18h 15m
Copa Airlines
Deal found 6/12![Copa Airlines logo]()
$525
This United Airlines deal was found by Cheapflights users on 6/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/149:40 pm
ORD
- SJO
1 stop13h 31m
United Airlines
sáb. 7/181:00 pm
SJO
- ORD
Nonstop5h 35m
United Airlines
Deal found 6/9![United Airlines logo]()
$492
This Copa Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/228:02 am
ORD
- SJO
1 stop25h 19m
Copa Airlines
dom. 7/268:45 am
SJO
- ORD
1 stop18h 15m
Copa Airlines
Deal found 6/12![Copa Airlines logo]()
$490
This Kiwi.com deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/228:02 am
ORD
- SJO
1 stop11h 59m
Copa Airlines
mar. 7/284:08 am
SJO
- ORD
1 stop8h 49m
Copa Airlines
Deal found 6/12![Copa Airlines logo]()
$521
This Orbitz deal was found by Cheapflights users on 6/10. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/245:13 pm
ORD
- SJO
1 stop16h 17m
Frontier
dom. 7/269:35 am
SJO
- ORD
1 stop22h 36m
Frontier
Deal found 6/10![Frontier logo]()
$478
This Expedia deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/314:09 pm
STL
- SJO
1 stop17h 21m
Frontier
jue. 8/69:35 am
SJO
- STL
1 stop13h 24m
Frontier
Deal found 6/10![Frontier logo]()
$498
One-way flights from Illinois to San JoséSearch for one-way flight options from Illinois to San José. Find affordable one-way fares based on user searches. Data last updated junio 12, 2026.
Search for one-way flight options from Illinois to San José. Find affordable one-way fares based on user searches. Data last updated junio 12, 2026.
This Southwest deal was found by Cheapflights users on 6/8. 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.
lun. 8/3110:05 am
MDW
- SJO
2 stops9h 35m
Southwest
Deal found 6/8![Southwest logo]()
$135
This Cheapflightsfares deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/87:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 6/12![JetBlue logo]()
$155
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/138:35 pm
MDW
- SJO
1 stop10h 25m
Southwest
Deal found 6/12![Southwest logo]()
$160
This Faresmojo deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/217:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 6/11![JetBlue logo]()
$164
This SmartFares deal was found by Cheapflights users on 6/8. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/307:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 6/8![JetBlue logo]()
$175
This Super.com deal was found by Cheapflights users on 6/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/297:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 6/8![JetBlue logo]()
$177
This American Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/76:45 pm
STL
- SJO
1 stop17h 37m
American Airlines
Deal found 6/8![American Airlines logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/317:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 6/11![JetBlue logo]()
$185
This Ovago deal was found by Cheapflights users on 6/8. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/287:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 6/8![JetBlue logo]()
$189
This Southwest deal was found by Cheapflights users on 6/8. 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.
mié. 9/910:30 am
MDW
- SJO
1 stop9h 10m
Southwest
Deal found 6/8![Southwest logo]()
$190
This JetBlue deal was found by Cheapflights users on 6/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/137:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 6/10![JetBlue logo]()
$190
This Viva deal was found by Cheapflights users on 6/9. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/81:30 am
ORD
- SJO
1 stop24h 45m
Viva
Deal found 6/9![Viva logo]()
$191
Find flight deals from Illinois to San José
Keep the following information in mind while searching for Illinois to San José flight deals. Data was last updated junio 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $400 (Delta) |
One-way from | $135 (Southwest) |
Popular in | December |
Cheapest in | September |
Average price | $572 |
Good round-trip deal | $607 or less |
Good one-way deal | $434 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois to San José 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 junio 12, 2026.
Use the filters below to find and compare flights from Illinois to San José that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
sáb. 9/19
10:25 am-6:00 pm
1 stop8h 35m
San José Juan Santamaria Intl
mié. 9/23
1:40 pm-11:10 pm
1 stop8h 30m
$462
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
mié. 9/16
10:10 am-6:40 pm
2 stops9h 30m
San José Juan Santamaria Intl
sáb. 9/26
9:30 am-8:20 pm
2 stops9h 50m
$471
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
jue. 10/8
1:49 pm-11:59 pm
1 stop11h 10m
San José Juan Santamaria Intl
dom. 10/11
4:15 pm-12:09 pm
1 stop18h 54m
$481
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
dom. 8/16
8:02 am-8:19 am
1 stop25h 17m
San José Juan Santamaria Intl
mié. 8/19
8:45 am-1:02 am
1 stop15h 17m
$490
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
mié. 9/30
8:01 am-6:59 pm
1 stop11h 58m
San José Juan Santamaria Intl
dom. 10/4
5:45 am-12:57 am
1 stop18h 12m
$490
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
mar. 8/4
3:21 pm-8:19 am
1 stop17h 58m
San José Juan Santamaria Intl
lun. 8/10
4:08 am-1:02 am
1 stop19h 54m
$490
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
vie. 10/23
3:20 pm-9:04 am
1 stop18h 44m
San José Juan Santamaria Intl
vie. 10/30
10:26 am-1:05 am
1 stop13h 39m
$490
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
sáb. 8/1
8:02 am-7:10 am
1 stop24h 08m
San José Juan Santamaria Intl
vie. 8/7
4:08 am-1:02 am
1 stop19h 54m
$490
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
mié. 7/22
3:21 pm-9:06 am
1 stop18h 45m
San José Juan Santamaria Intl
dom. 7/26
5:45 am-4:00 am
1 stop21h 15m
$490
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
lun. 7/27
3:21 pm-9:06 am
1 stop18h 45m
San José Juan Santamaria Intl
mié. 8/5
10:03 am-1:59 pm
1 stop26h 56m
$490
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Illinois to San José
Have a flexible travel schedule? Discover the best time to fly to San José from Illinois with our price prediction graph.
MDW-SJO
ORD-SJO
STL-SJO
MLI-SJO
BMI-SJO
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 Illinois to San José
USIL-SJO
MDW-SJO
ORD-SJO
STL-SJO
MLI-SJO
What is the cheapest month to book a flight from Illinois to San José?
Currently, August is the cheapest month in which you can book a flight from Illinois to San José (average of $88). Flying from Illinois to San José in December is currently the most expensive (average of $2,688). 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 IL to SJO?
Find hourly flight availability from Illinois to San José. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated junio 12, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to San José as you normally would.
How much does it cost to fly round-trip from Illinois to San José?
How far ahead should I book a flight from Illinois to San José?
Booking 8 days in advance of your planned departure date is, on average, the best time to get cheap flights from Illinois to San José. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Related info for your journey
Find useful and relevant information for your journey from Illinois to San José. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near San José?
Book flights to San José if you plan to visit one of these locationsAlajuela
Jacó
Heredia
Dominical
Manuel Antonio
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Illinois and San José flights
Browse other Illinois and San José flight options. Last updated on junio 12, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Other flights to San José
Explore flights to San José departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on junio 12, 2026.
Illinois to San José flights
Consider these flights traveling from Illinois to San José.
Top 9 airlines flying from Illinois to San José
Discover the top 9 airlines that operate flights from Illinois to San José. 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 junio 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$139 | Average$562 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$221 | Average$547 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$271 | Average$796 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$303 | Average$479 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$341 | Average$627 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$383 | Average$588 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$384 | Average$740 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$386 | Average$518 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$628 | Average$664 | FlexibilityNo cancel fee | On-time67% |