$219+ Cheap flights from San José (SJO) to O'Hare Intl (ORD)
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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — ORD
Jun 23 — Jun 301
Round-trip
1 adult, Economy
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Find cheap flights from San José to O'Hare Intl 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 San José Juan Santamaria Intl to Chicago O'Hare Intl are usually found in February or January, booked 90 days in advance, depart on a Tuesday or Thursday and return on a Tuesday
Cheap flight deals from San José to O'Hare Intl
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Best
Last-minute
One-way
Cheapest flights from San José to O'Hare IntlExplore the most affordable flight options available from San José to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 24, 2026.
Explore the most affordable flight options available from San José to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 24, 2026.
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Tue 9/87:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 5/20![JetBlue logo]()
$383
This Volaris deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/154:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Tue 10/201:49 pm
ORD
- SJO
1 stop11h 10m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$401
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.
Thu 5/219:00 am
SJO
- ORD
1 stop11h 55m
Southwest
Tue 5/265:55 am
ORD
- SJO
1 stop7h 15m
Southwest
Deal found 5/19![Southwest logo]()
$411
This Air Canada deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/157:15 am
SJO
- ORD
2 stops23h 30m
Air Canada
Wed 6/176:22 pm
ORD
- SJO
2 stops28h 38m
Air Canada
Deal found 5/22![Air Canada logo]()
$420
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/134:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Mon 10/192:53 am
ORD
- SJO
1 stop22h 06m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$423
This Volaris deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/154:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Sat 10/172:53 am
ORD
- SJO
1 stop22h 06m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$424
This Air Canada deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:15 am
SJO
- ORD
1 stop11h 53m
Air Canada
Tue 6/29:55 am
ORD
- SJO
1 stop13h 05m
Air Canada
Deal found 5/22![Air Canada logo]()
$433
This eDestinos deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/104:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Tue 9/151:49 pm
ORD
- SJO
1 stop11h 10m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$437
This Viva deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/142:20 am
SJO
- ORD
1 stop21h 20m
Viva
Sun 8/161:30 am
ORD
- SJO
1 stop24h 45m
Viva
Deal found 5/23![Viva logo]()
$438
This Air Canada deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:15 am
SJO
- ORD
1 stop11h 53m
Air Canada
Sat 6/69:20 pm
ORD
- SJO
2 stops24h 15m
Air Canada
Deal found 5/23![Air Canada logo]()
$441
This JetBlue deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/162:05 pm
SJO
- ORD
1 stop8h 39m
JetBlue
Tue 9/227:00 am
ORD
- SJO
1 stop6h 55m
JetBlue
Deal found 5/23![JetBlue logo]()
$442
Best flights from San José to O'Hare IntlDiscover carefully curated flight deals from San José to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 24, 2026.
Discover carefully curated flight deals from San José to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 24, 2026.
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/611:01 am
SJO
- ORD
1 stop25h 45m
Copa Airlines
Mon 11/97:35 am
ORD
- SJO
1 stop24h 46m
Copa Airlines
Deal found 5/19![Copa Airlines logo]()
$473
This United Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:55 am
SJO
- ORD
1 stop11h 10m
United Airlines
Thu 9/179:35 pm
ORD
- SJO
1 stop23h 02m
United Airlines
Deal found 5/23![United Airlines logo]()
$476
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:03 am
SJO
- ORD
1 stop13h 59m
Copa Airlines
Mon 8/248:02 am
ORD
- SJO
1 stop11h 57m
Copa Airlines
Deal found 5/19![Copa Airlines logo]()
$473
This United Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:55 am
SJO
- ORD
1 stop11h 10m
United Airlines
Sat 9/267:55 pm
ORD
- SJO
1 stop17h 26m
United Airlines
Deal found 5/24![United Airlines logo]()
$485
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:17 pm
SJO
- ORD
1 stop18h 42m
Copa Airlines
Mon 8/173:21 pm
ORD
- SJO
1 stop17h 58m
Copa Airlines
Deal found 5/21![Copa Airlines logo]()
$473
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/134:08 am
SJO
- ORD
1 stop19h 54m
Copa Airlines
Sat 9/193:20 pm
ORD
- SJO
1 stop18h 44m
Copa Airlines
Deal found 5/20![Copa Airlines logo]()
$473
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:55 pm
SJO
- ORD
1 stop19h 04m
Copa Airlines
Wed 8/198:02 am
ORD
- SJO
1 stop25h 17m
Copa Airlines
Deal found 5/19![Copa Airlines logo]()
$473
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:03 am
SJO
- ORD
1 stop13h 59m
Copa Airlines
Tue 9/228:01 am
ORD
- SJO
1 stop26h 03m
Copa Airlines
Deal found 5/19![Copa Airlines logo]()
$473
This Copa Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:45 am
SJO
- ORD
1 stop17h 17m
Copa Airlines
Sat 8/88:02 am
ORD
- SJO
1 stop25h 17m
Copa Airlines
Deal found 5/22![Copa Airlines logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:55 pm
SJO
- ORD
1 stop19h 04m
Copa Airlines
Sat 8/223:21 pm
ORD
- SJO
1 stop17h 58m
Copa Airlines
Deal found 5/23![Copa Airlines logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/24:08 am
SJO
- ORD
1 stop19h 49m
Copa Airlines
Fri 10/93:20 pm
ORD
- SJO
1 stop17h 59m
Copa Airlines
Deal found 5/23![Copa Airlines logo]()
$494
Last-minute flights from San José to O'Hare IntlDiscover last-minute flight deals from San José to O'Hare Intl. Data last updated May 24, 2026 and is based on user searches.
Discover last-minute flight deals from San José to O'Hare Intl. Data last updated May 24, 2026 and is based on user searches.
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.
Thu 5/219:00 am
SJO
- ORD
1 stop11h 55m
Southwest
Tue 5/265:55 am
ORD
- SJO
1 stop7h 15m
Southwest
Deal found 5/19![Southwest logo]()
$411
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/257:15 am
SJO
- ORD
2 stops27h 06m
Air Canada
Tue 6/99:55 am
ORD
- SJO
1 stop13h 05m
Air Canada
Deal found 5/21![Air Canada logo]()
$452
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/257:15 am
SJO
- ORD
2 stops27h 06m
Air Canada
Sat 6/65:35 pm
ORD
- SJO
2 stops28h 00m
Air Canada
Deal found 5/21![Air Canada logo]()
$455
This Air Canada deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:15 am
SJO
- ORD
1 stop11h 53m
Air Canada
Tue 6/29:55 am
ORD
- SJO
1 stop13h 05m
Air Canada
Deal found 5/22![Air Canada logo]()
$433
This Air Canada deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:15 am
SJO
- ORD
1 stop11h 53m
Air Canada
Sat 6/69:20 pm
ORD
- SJO
2 stops24h 15m
Air Canada
Deal found 5/23![Air Canada logo]()
$441
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:15 am
SJO
- ORD
1 stop11h 53m
Air Canada
Tue 6/99:55 am
ORD
- SJO
1 stop13h 05m
Air Canada
Deal found 5/21![Air Canada logo]()
$444
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:15 am
SJO
- ORD
1 stop11h 53m
Air Canada
Sat 6/139:20 pm
ORD
- SJO
2 stops24h 15m
Air Canada
Deal found 5/21![Air Canada logo]()
$458
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:15 am
SJO
- ORD
2 stops25h 35m
Air Canada
Mon 6/88:20 pm
ORD
- SJO
1 stop26h 40m
Air Canada
Deal found 5/21![Air Canada logo]()
$463
This Mytrip deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/24:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Thu 6/119:55 am
ORD
- SJO
1 stop13h 05m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$461
This Air Canada deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/157:15 am
SJO
- ORD
2 stops23h 30m
Air Canada
Wed 6/176:22 pm
ORD
- SJO
2 stops28h 38m
Air Canada
Deal found 5/22![Air Canada logo]()
$420
One-way flights from San José to O'Hare IntlSearch for one-way flight options from San José to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated May 24, 2026.
Search for one-way flight options from San José to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated May 24, 2026.
This Viva 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/152:20 am
SJO
- ORD
1 stop20h 35m
Viva
Deal found 5/21![Viva logo]()
$219
This Super.com deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/162:05 pm
SJO
- ORD
1 stop8h 39m
JetBlue
Deal found 5/23![JetBlue logo]()
$225
This Ovago 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/72:05 pm
SJO
- ORD
1 stop8h 39m
JetBlue
Deal found 5/19![JetBlue logo]()
$230
This Viva deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/142:20 am
SJO
- ORD
1 stop21h 20m
Viva
Deal found 5/23![Viva logo]()
$240
This Expedia deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:15 am
SJO
- ORD
1 stop11h 53m
Air Canada
Deal found 5/23![Air Canada logo]()
$241
This Viva 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/192:20 am
SJO
- ORD
1 stop21h 20m
Viva
Deal found 5/20![Viva logo]()
$244
This Justfly.com deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/227:15 am
SJO
- ORD
1 stop23h 35m
Air Canada
Deal found 5/22![Air Canada logo]()
$246
This Viva 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/12:20 am
SJO
- ORD
1 stop20h 35m
Viva
Deal found 5/21![Viva logo]()
$248
This Viva deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/112:20 am
SJO
- ORD
1 stop20h 35m
Viva
Deal found 5/22![Viva logo]()
$249
This Volaris deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/74:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$263
Find flight deals from San José to O'Hare Intl
Discover tips and strategies to find the most affordable flight options for your journey from San José (SJO) to O'Hare Intl (ORD). 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 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $361 (Viva) |
One-way from | $219 (Viva) |
Popular in | March |
Cheapest in | February |
Average price | $492 |
Good round-trip deal | $364 or less |
Good one-way deal | $230 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San José to O'Hare Intl 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 24, 2026.
Use the filters below to find and compare flights from San José to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Fri 11/6
11:01 am-12:46 pm
1 stop25h 45m
Chicago O'Hare Intl
Mon 11/9
7:35 am-8:21 am
1 stop24h 46m
$473
Quickest round-trip
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 8/19
10:03 am-1:02 am
1 stop13h 59m
Chicago O'Hare Intl
Mon 8/24
8:02 am-6:59 pm
1 stop11h 57m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 8/11
6:17 pm-1:59 pm
1 stop18h 42m
Chicago O'Hare Intl
Mon 8/17
3:21 pm-8:19 am
1 stop17h 58m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sun 9/13
4:08 am-1:02 am
1 stop19h 54m
Chicago O'Hare Intl
Sat 9/19
3:20 pm-9:04 am
1 stop18h 44m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 8/12
5:55 pm-1:59 pm
1 stop19h 04m
Chicago O'Hare Intl
Wed 8/19
8:02 am-8:19 am
1 stop25h 17m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 9/17
10:03 am-1:02 am
1 stop13h 59m
Chicago O'Hare Intl
Tue 9/22
8:01 am-9:04 am
1 stop26h 03m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 9/16
7:55 am-8:05 pm
1 stop11h 10m
Chicago O'Hare Intl
Thu 9/17
9:35 pm-7:37 pm
1 stop23h 02m
$476
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 9/19
7:55 am-8:05 pm
1 stop11h 10m
Chicago O'Hare Intl
Sat 9/26
7:55 pm-12:21 pm
1 stop17h 26m
$485
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 8/1
5:45 am-12:02 am
1 stop17h 17m
Chicago O'Hare Intl
Sat 8/8
8:02 am-8:19 am
1 stop25h 17m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 8/18
5:55 pm-1:59 pm
1 stop19h 04m
Chicago O'Hare Intl
Sat 8/22
3:21 pm-8:19 am
1 stop17h 58m
$494
Showing 1-10 of 22 resultsSorted by cheapest first
Compare providers for flights from San José to O'Hare Intl
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 San José to O'Hare Intl in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San José-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San José-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San José-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San José-Chicago O'Hare Intl Airport 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 San José-Chicago O'Hare Intl Airport 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 San José to O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from San José with our price prediction graph.
SJO-ORD
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 José to Chicago O'Hare Intl Airport
Prices
Delays
How far ahead should I book a flight from San José to Chicago O'Hare Intl Airport?
The price you pay for your flight from San José to Chicago O'Hare Intl Airport may vary depending on when you book. For the best chance of a lower fare, look to book 89 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from San José to Chicago O'Hare Intl Airport?
Currently, February is the cheapest month in which you can book a flight from San José to Chicago O'Hare Intl Airport (average of $386). Flying from San José to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $559). 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 SJO to ORD?
Find hourly flight availability from San José to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 24, 2026.
When flying from San José to Chicago O'Hare Intl Airport, 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 San José to Chicago delayed?
About 7% of weekly flights between San José and Chicago have experienced delays in the past year, with the average delay time being 238 minutes.
What is the most punctual flight time for San José to Chicago 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?
Tuesday 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 San José to Chicago flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 6% of flights being delayed.
Reviews of airlines servicing O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated May 24, 2026.
See what other customers who have flown with Copa Airlines,United Airlines, andAmerican Airlines from San José to Chicago O'Hare Intl Airport have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.8
Crew
8.1
Entertainment
6.8
Overall
7.5
Comfort
7.4
Food
6.9
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Boarding
7.8
Crew
8.1
Entertainment
6.8
Overall
7.5
Comfort
7.4
Food
6.9
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Boarding
7.8
Crew
8.1
Entertainment
6.8
Overall
7.5
Comfort
7.4
Food
6.9
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Boarding
7.8
Crew
8.1
Entertainment
6.8
Overall
7.5
Comfort
7.4
Food
6.9
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Boarding
7.8
Crew
8.1
Entertainment
6.8
Overall
7.5
Comfort
7.4
Food
6.9
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Spirit Airlines
Boarding
7.8
Crew
8.1
Entertainment
6.8
Overall
7.5
Comfort
7.4
Food
6.9
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Related info for your journey
Find useful and relevant information for your journey from San José to O'Hare Intl. 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 Chicago O'Hare Intl Airport?
Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locationsRosemont
Schaumburg
Benton Harbor
Naperville
Delavan
Oakbrook Terrace
Lake Geneva
Gurnee
Downers Grove
Des Plaines
Hoffman Estates
Oak Brook
South Holland
Libertyville
Warrenville
Great Lakes
Arlington Heights
Northbrook
Waukegan
Rockford
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Other flights to O'Hare Intl
Explore flights to O'Hare Intl departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 24, 2026.
San José and O'Hare Intl flights
Browse other San José and O'Hare Intl flight options. Last updated on May 24, 2026.
Other flights from San José
Browse through other flights departing from San José. Flights are based on user searches made on Cheapflights and were last updated on May 24, 2026.
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Top 5 airlines flying from San José to O'Hare Intl
Discover the top 5 airlines that operate flights from San José to O'Hare Intl. 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 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$179 | Average$292 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$189 | Average$482 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$249 | Average$504 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$332 | Average$514 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$370 | Average$472 | FlexibilityNo cancel fee | On-time69% |