$155+ Cheap flights from O'Hare Intl (ORD) 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJO
Jun 16 — Jun 231
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to San José with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago O'Hare Intl to San José Juan Santamaria Intl are usually found in October or September, booked 44 days in advance, depart on a Tuesday or Monday and return on a Tuesday
Cheap flight deals from O'Hare Intl to San José
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Best
Last-minute
One-way
Cheapest flights from O'Hare Intl to San JoséExplore the most affordable flight options available from O'Hare Intl to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 17, 2026.
Explore the most affordable flight options available from O'Hare Intl to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 17, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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.
Mon 8/317:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Tue 9/82:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 5/14![JetBlue logo]()
$430
This Kiwi.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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.
Tue 8/111:50 pm
ORD
- SJO
2 stops43h 30m
Frontier
Fri 8/219:35 am
SJO
- ORD
1 stop12h 39m
Frontier
Deal found 5/15![Frontier logo]()
$431
This Priceline deal was found by Cheapflights users on 5/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/44:59 pm
ORD
- SJO
1 stop16h 21m
Multiple Airlines
Fri 7/102:02 pm
SJO
- ORD
1 stop8h 42m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$432
This Air Canada deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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.
Sun 6/148:45 am
ORD
- SJO
1 stop12h 50m
Air Canada
Mon 6/227:15 am
SJO
- ORD
2 stops23h 30m
Air Canada
Deal found 5/14![Air Canada logo]()
$434
This JetBlue deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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.
Tue 8/117:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Sat 8/222:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 5/15![JetBlue logo]()
$435
This CheapOair deal was found by Cheapflights users on 5/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:13 pm
ORD
- SJO
1 stop16h 07m
Multiple Airlines
Fri 8/72:02 pm
SJO
- ORD
1 stop8h 42m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$437
This Super.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Tue 8/117:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Mon 8/172:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 5/13![JetBlue logo]()
$438
This Super.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Sun 8/237:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Sun 8/302:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 5/13![JetBlue logo]()
$440
This Air Canada deal was found by Cheapflights users on 5/12. 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.
Sun 6/148:45 am
ORD
- SJO
1 stop12h 50m
Air Canada
Tue 6/237:10 am
SJO
- ORD
1 stop29h 12m
Air Canada
Deal found 5/12![Air Canada logo]()
$444
This Cheapflightsfares deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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.
Wed 8/57:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Thu 8/132:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 5/14![JetBlue logo]()
$445
Best flights from O'Hare Intl to San JoséDiscover carefully curated flight deals from O'Hare Intl to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 17, 2026.
Discover carefully curated flight deals from O'Hare Intl to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 17, 2026.
This Copa Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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.
Sun 7/123:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
Wed 7/1510:03 am
SJO
- ORD
1 stop16h 57m
Copa Airlines
Deal found 5/14![Copa Airlines logo]()
$470
This JetBlue deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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.
Wed 7/297:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Thu 7/302:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 5/15![JetBlue logo]()
$490
This United Airlines deal was found by Cheapflights users on 5/12. 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.
Sat 7/47:36 am
ORD
- SJO
Nonstop5h 19m
United Airlines
Sat 7/111:00 pm
SJO
- ORD
Nonstop5h 35m
United Airlines
Deal found 5/12![United Airlines logo]()
$549
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 8/105:28 am
ORD
- SJO
1 stop7h 21m
Delta
Tue 8/181:14 pm
SJO
- ORD
2 stops17h 42m
Delta
Deal found 5/14![Delta logo]()
$606
This Copa Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Fri 7/33:21 pm
ORD
- SJO
1 stop17h 05m
Copa Airlines
Sun 7/121:37 pm
SJO
- ORD
1 stop13h 23m
Copa Airlines
Deal found 5/13![Copa Airlines logo]()
$470
This Copa Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Fri 8/73:21 pm
ORD
- SJO
1 stop18h 43m
Copa Airlines
Sun 8/165:55 pm
SJO
- ORD
1 stop19h 04m
Copa Airlines
Deal found 5/13![Copa Airlines logo]()
$505
This JetBlue deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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.
Fri 8/147:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Sat 8/222:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 5/15![JetBlue logo]()
$568
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.
Sat 7/46:35 am
ORD
- SJO
1 stop7h 32m
Delta
Tue 7/211:16 pm
SJO
- ORD
1 stop18h 19m
Delta
Deal found 5/16![Delta logo]()
$611
This Copa Airlines deal was found by Cheapflights users on 5/12. 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.
Sun 7/263:21 pm
ORD
- SJO
1 stop17h 05m
Copa Airlines
Tue 8/45:45 am
SJO
- ORD
1 stop18h 17m
Copa Airlines
Deal found 5/12![Copa Airlines logo]()
$505
This JetBlue deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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.
Sat 8/87:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Sat 8/222:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 5/15![JetBlue logo]()
$568
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.
Sun 6/285:30 am
ORD
- SJO
1 stop7h 24m
Delta
Thu 7/231:16 pm
SJO
- ORD
2 stops17h 43m
Delta
Deal found 5/16![Delta logo]()
$616
This Copa Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Thu 6/188:02 am
ORD
- SJO
1 stop11h 57m
Copa Airlines
Sun 6/216:19 pm
SJO
- ORD
1 stop8h 41m
Copa Airlines
Deal found 5/13![Copa Airlines logo]()
$556
Last-minute flights from O'Hare Intl to San JoséDiscover last-minute flight deals from O'Hare Intl to San José. Data last updated May 17, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to San José. Data last updated May 17, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 5/12. 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.
Fri 6/56:22 pm
ORD
- SJO
2 stops28h 38m
Air Canada
Mon 6/87:15 am
SJO
- ORD
2 stops23h 45m
Air Canada
Deal found 5/12![Air Canada logo]()
$453
This Air Canada deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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.
Sat 6/62:00 pm
ORD
- SJO
2 stops31h 35m
Air Canada
Tue 6/237:10 am
SJO
- ORD
1 stop30h 45m
Air Canada
Deal found 5/15![Air Canada logo]()
$473
This Air Canada deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Thu 6/119:20 pm
ORD
- SJO
2 stops24h 15m
Air Canada
Mon 6/157:15 am
SJO
- ORD
2 stops23h 30m
Air Canada
Deal found 5/13![Air Canada logo]()
$447
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/128:20 pm
ORD
- SJO
1 stop26h 40m
Air Canada
Mon 6/227:15 am
SJO
- ORD
2 stops29h 51m
Air Canada
Deal found 5/16![Air Canada logo]()
$452
This Air Canada deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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.
Sun 6/148:45 am
ORD
- SJO
1 stop12h 50m
Air Canada
Mon 6/227:15 am
SJO
- ORD
2 stops23h 30m
Air Canada
Deal found 5/14![Air Canada logo]()
$434
This Air Canada deal was found by Cheapflights users on 5/12. 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.
Sun 6/148:45 am
ORD
- SJO
1 stop12h 50m
Air Canada
Tue 6/237:10 am
SJO
- ORD
1 stop29h 12m
Air Canada
Deal found 5/12![Air Canada logo]()
$444
This Air Canada deal was found by Cheapflights users on 5/12. 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.
Sun 6/147:25 am
ORD
- SJO
2 stops14h 10m
Air Canada
Wed 6/247:10 am
SJO
- ORD
1 stop29h 13m
Air Canada
Deal found 5/12![Air Canada logo]()
$474
This Copa Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Mon 6/153:21 pm
ORD
- SJO
1 stop18h 00m
Copa Airlines
Fri 6/195:57 pm
SJO
- ORD
1 stop9h 03m
Copa Airlines
Deal found 5/13![Copa Airlines logo]()
$470
One-way flights from O'Hare Intl to San JoséSearch for one-way flight options from O'Hare Intl to San José. Find affordable one-way fares based on user searches. Data last updated May 17, 2026.
Search for one-way flight options from O'Hare Intl to San José. Find affordable one-way fares based on user searches. Data last updated May 17, 2026.
This JetBlue deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Tue 8/117:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 5/13![JetBlue logo]()
$155
This Expedia deal was found by Cheapflights users on 5/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/315:13 pm
ORD
- SJO
1 stop16h 07m
Frontier
Deal found 5/12![Frontier logo]()
$158
This CheapOair deal was found by Cheapflights users on 5/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/295:13 pm
ORD
- SJO
1 stop16h 07m
Frontier
Deal found 5/12![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Tue 8/111:50 pm
ORD
- SJO
2 stops43h 30m
Frontier
Deal found 5/13![Frontier logo]()
$164
This Priceline deal was found by Cheapflights users on 5/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/14:59 pm
ORD
- SJO
1 stop16h 21m
Frontier
Deal found 5/12![Frontier logo]()
$178
This Cheapflightsfares deal was found by Cheapflights users on 5/12. 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.
Wed 8/127:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 5/12![JetBlue logo]()
$180
This Super.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Sat 5/235:11 pm
ORD
- SJO
1 stop16h 08m
Frontier
Deal found 5/13![Frontier logo]()
$184
This Expedia deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 8/87:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 5/13![JetBlue logo]()
$185
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:35 pm
ORD
- SJO
1 stop26h 25m
Air Canada
Deal found 5/16![Air Canada logo]()
$189
This Viva deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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.
Fri 8/71:30 am
ORD
- SJO
1 stop24h 45m
Viva
Deal found 5/14![Viva logo]()
$190
This Air Canada deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Sat 5/303:40 pm
ORD
- SJO
1 stop29h 55m
Air Canada
Deal found 5/13![Air Canada logo]()
$195
Find flight deals from O'Hare Intl to San José
Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to San José (SJO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $431 (Kiwi.com) |
One-way from | $155 (JetBlue) |
Popular in | December |
Cheapest in | October |
Average price | $560 |
Good round-trip deal | $497 or less |
Good one-way deal | $434 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl 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 May 17, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to San José that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sun 7/12
3:21 pm-9:06 am
1 stop18h 45m
San José Juan Santamaria Intl
Wed 7/15
10:03 am-4:00 am
1 stop16h 57m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Fri 7/3
3:21 pm-7:26 am
1 stop17h 05m
San José Juan Santamaria Intl
Sun 7/12
1:37 pm-4:00 am
1 stop13h 23m
$470
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Wed 7/29
7:00 am-12:57 pm
1 stop6h 57m
San José Juan Santamaria Intl
Thu 7/30
2:02 pm-11:44 pm
1 stop8h 42m
$490
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Fri 8/7
3:21 pm-9:04 am
1 stop18h 43m
San José Juan Santamaria Intl
Sun 8/16
5:55 pm-1:59 pm
1 stop19h 04m
$505
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sun 7/26
3:21 pm-7:26 am
1 stop17h 05m
San José Juan Santamaria Intl
Tue 8/4
5:45 am-1:02 am
1 stop18h 17m
$505
Quickest round-trip
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sat 7/4
7:36 am-11:55 am
Nonstop5h 19m
San José Juan Santamaria Intl
Sat 7/11
1:00 pm-7:35 pm
Nonstop5h 35m
$549
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Thu 6/18
8:02 am-6:59 pm
1 stop11h 57m
San José Juan Santamaria Intl
Sun 6/21
6:19 pm-4:00 am
1 stop8h 41m
$556
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Fri 8/14
7:00 am-12:57 pm
1 stop6h 57m
San José Juan Santamaria Intl
Sat 8/22
2:02 pm-11:44 pm
1 stop8h 42m
$568
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sat 8/8
7:00 am-12:57 pm
1 stop6h 57m
San José Juan Santamaria Intl
Sat 8/22
2:02 pm-11:44 pm
1 stop8h 42m
$568
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Mon 8/10
5:28 am-11:49 am
1 stop7h 21m
San José Juan Santamaria Intl
Tue 8/18
1:14 pm-7:56 am
2 stops17h 42m
$606
Showing 1-10 of 23 resultsSorted by cheapest first
Compare providers for flights from O'Hare Intl to San José
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to San José in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-San José flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-San José flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-San José flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-San José flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-San José flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from O'Hare Intl to San José
Have a flexible travel schedule? Discover the best time to fly to San José from O'Hare Intl with our price prediction graph.
ORD-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 Chicago O'Hare Intl Airport to San José
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How far ahead should I book a flight from Chicago O'Hare Intl Airport to San José?
To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to San José, you should look to book at least 43 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to San José?
Currently, October is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to San José (average of $359). Flying from Chicago O'Hare Intl Airport to San José in December is currently the most expensive (average of $679). 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 ORD to SJO?
Find hourly flight availability from O'Hare Intl 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 May 17, 2026.
When flying from Chicago O'Hare Intl Airport to San José, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How often are flights from Chicago to San José delayed?
About 20% of weekly flights between Chicago and San José have experienced delays in the past year, with the average delay time being 158 minutes.
What is the most punctual flight time for Chicago to San José flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to San José flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 14% of flights being delayed.
What’s the top layover airport for flights from Chicago O'Hare Intl Airport to San José?
Share of 1-stop round-trip flights from Chicago O'Hare Intl Airport to San José chosen by Cheapflights users in the past 12 months, using the same layover each way.
Panama City (PTY) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago O'Hare Intl Airport to San José on Cheapflights.
What’s the cheapest layover airport for flights from Chicago O'Hare Intl Airport to San José?
Average round-trip fare for 1-stop flights from Chicago O'Hare Intl Airport to San José, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Fort Lauderdale (FLL) is the most affordable 1-stop option, with an average round-trip price of $371.
What’s the fastest layover option from Chicago O'Hare Intl Airport to San José?
Shortest average travel time for 1-stop one-way flights from Chicago O'Hare Intl Airport to San José, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Fort Lauderdale (FLL) have the shortest average one-way travel time for 1-stop routes: 7h 06m.
Which airport typically offers the quickest layover for flights from Chicago O'Hare Intl Airport to San José?
Average layover duration for 1-stop one-way flights from Chicago O'Hare Intl Airport to San José, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Panama City (PTY) offer the fastest connection on this route, with an average layover time of 1h 29m.
Reviews of airlines servicing San José
Get insights into the airlines that provide service to San José. 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 San José. Reviews last updated May 17, 2026.
See what other customers who have flown with Copa Airlines,United Airlines, andAmerican Airlines from Chicago O'Hare Intl Airport to San José have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.8
Boarding
7.7
Overall
7.5
Crew
8.1
Entertainment
6.8
Comfort
7.4
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Food
6.8
Boarding
7.7
Overall
7.5
Crew
8.1
Entertainment
6.8
Comfort
7.4
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Food
6.8
Boarding
7.7
Overall
7.5
Crew
8.1
Entertainment
6.8
Comfort
7.4
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Food
6.8
Boarding
7.7
Overall
7.5
Crew
8.1
Entertainment
6.8
Comfort
7.4
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Food
6.8
Boarding
7.7
Overall
7.5
Crew
8.1
Entertainment
6.8
Comfort
7.4
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Food
6.8
Boarding
7.7
Overall
7.5
Crew
8.1
Entertainment
6.8
Comfort
7.4
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl 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
Monteverde
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Heredia
Dominical
Manuel Antonio
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O'Hare Intl and San José flights
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Top 10 airlines flying from O'Hare Intl to San José
Discover the top 10 airlines that operate flights from O'Hare Intl 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 May 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$139 | Average$386 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$205 | Average$482 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$232 | Average$357 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$271 | Average$796 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$303 | Average$474 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$341 | Average$563 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$384 | Average$578 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$384 | Average$788 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$386 | Average$529 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$628 | Average$661 | FlexibilityNo cancel fee | On-time67% |