$234+ Cheap flights from O'Hare Intl (ORD) to San José (SJO)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJO
Oct 29 — Nov 51
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 February, booked 44 days in advance, depart on a Monday or Tuesday and return on a Tuesday
Cheap flight deals from O'Hare Intl to San José
Cheapest
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 September 29, 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 September 29, 2026.
This Booking.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/313:13 pm -
1 stop16h 49m
Sat 11/710:03 am -
1 stop14h 08m
Deal found 9/25![Copa Airlines logo]()
$401
This Avianca deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/410:30 pm -
1 stop10h 20m
Tue 11/101:55 am -
1 stop18h 35m
Deal found 9/29![Avianca logo]()
$404
This Copa Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 11/22:13 pm -
1 stop22h 06m
Sun 11/810:03 am -
1 stop26h 43m
Deal found 9/28![Copa Airlines logo]()
$406
This Avianca deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/910:30 pm -
1 stop10h 20m
Wed 12/165:35 am -
1 stop7h 20m
Deal found 9/28![Avianca logo]()
$407
This Avianca deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/52:20 pm -
1 stop18h 15m
Fri 12/185:35 am -
1 stop7h 20m
Deal found 9/29![Avianca logo]()
$409
This Avianca deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/32:20 pm -
1 stop8h 55m
Sun 12/205:35 am -
1 stop7h 20m
Deal found 9/28![Avianca logo]()
$410
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:27 am -
1 stop7h 33m
Mon 11/22:25 pm -
1 stop9h 32m
Deal found 9/27![Delta logo]()
$418
This American Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:30 am -
2 stops12h 20m
Thu 11/122:01 pm -
1 stop9h 55m
Deal found 9/28![American Airlines logo]()
$423
This Justfly.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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.
Tue 10/2711:30 pm -
1 stop26h 00m
Mon 11/21:50 am -
1 stop18h 40m
Deal found 9/27![Avianca logo]()
$427
This American Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:29 am -
2 stops12h 52m
Sun 11/13:54 pm -
1 stop16h 05m
Deal found 9/28![American Airlines logo]()
$428
This FlightHub deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1110:30 pm -
1 stop26h 00m
Mon 1/115:35 am -
1 stop7h 20m
Deal found 9/29![Avianca logo]()
$429
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 September 29, 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 September 29, 2026.
This Copa Airlines deal was found by Cheapflights users on 9/24. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/22:13 pm -
1 stop18h 54m
Thu 11/1210:03 am -
1 stop14h 08m
Deal found 9/24![Copa Airlines logo]()
$406
This United Airlines deal was found by Cheapflights users on 9/24. 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 11/287:17 am -
Nonstop5h 18m
Sat 12/126:40 am -
1 stop15h 25m
Deal found 9/24![United Airlines logo]()
$598
This Delta deal was found by Cheapflights users on 9/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:49 am -
1 stop15h 26m
Mon 12/147:00 am -
1 stop10h 02m
Deal found 9/24![Delta logo]()
$616
This Copa Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 11/252:13 pm -
1 stop22h 06m
Wed 12/25:35 am -
1 stop18h 36m
Deal found 9/26![Copa Airlines logo]()
$473
This United Airlines deal was found by Cheapflights users on 9/24. 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 11/77:17 am -
Nonstop5h 18m
Sun 11/152:25 pm -
1 stop10h 20m
Deal found 9/24![United Airlines logo]()
$679
This Copa Airlines deal was found by Cheapflights users on 9/24. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/252:13 pm -
1 stop16h 52m
Tue 1/192:15 pm -
1 stop9h 52m
Deal found 9/24![Copa Airlines logo]()
$673
This United Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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.
Sun 12/139:00 am -
1 stop10h 53m
Sat 12/191:25 pm -
Nonstop5h 32m
Deal found 9/28![United Airlines logo]()
$701
This United Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 12/57:30 am -
1 stop13h 09m
Sun 12/201:25 pm -
Nonstop5h 32m
Deal found 9/27![United Airlines logo]()
$702
This United Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 11/79:25 am -
1 stop11h 14m
Sat 11/141:55 pm -
Nonstop5h 33m
Deal found 9/25![United Airlines logo]()
$766
This United Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 12/125:55 am -
1 stop13h 58m
Mon 12/211:25 pm -
Nonstop5h 32m
Deal found 9/25![United Airlines logo]()
$779
This United Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/129:45 pm -
1 stop22h 52m
Sun 10/187:55 am -
1 stop15h 28m
Deal found 9/28![United Airlines logo]()
$949
Last-minute flights from O'Hare Intl to San JoséDiscover last-minute flight deals from O'Hare Intl to San José. Data last updated September 29, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to San José. Data last updated September 29, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:00 am -
1 stop16h 07m
Sun 10/41:00 pm -
1 stop17h 35m
Deal found 9/25![American Airlines logo]()
$457
This American Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:43 am -
1 stop12h 38m
Tue 10/271:00 pm -
1 stop17h 35m
Deal found 9/26![American Airlines logo]()
$435
This American Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:40 am -
2 stops12h 41m
Mon 10/193:01 pm -
1 stop15h 46m
Deal found 9/25![American Airlines logo]()
$440
This KAYAK deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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.
Mon 10/1911:20 pm -
1 stop17h 05m
Fri 10/239:25 am -
1 stop10h 55m
Deal found 9/28![Avianca logo]()
$452
This Avianca deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2311:20 pm -
1 stop10h 30m
Sun 11/19:30 am -
1 stop11h 00m
Deal found 9/29![Avianca logo]()
$404
This Justfly.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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.
Tue 10/2711:30 pm -
1 stop26h 00m
Mon 11/21:50 am -
1 stop18h 40m
Deal found 9/27![Avianca logo]()
$427
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:27 am -
1 stop7h 33m
Tue 11/32:25 pm -
1 stop9h 32m
Deal found 9/27![Delta logo]()
$418
This American Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:29 am -
2 stops12h 52m
Sun 11/13:54 pm -
1 stop16h 05m
Deal found 9/28![American Airlines logo]()
$428
This Copa Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/303:13 pm -
1 stop16h 51m
Mon 11/210:03 am -
1 stop14h 08m
Deal found 9/28![Copa Airlines logo]()
$406
This Booking.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/313:13 pm -
1 stop16h 49m
Sat 11/710:03 am -
1 stop14h 08m
Deal found 9/25![Copa Airlines logo]()
$401
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 September 29, 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 September 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:44 pm -
2 stops37h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Frontier logo]()
$234
This FlightHub deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/251:49 pm -
1 stop11h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/28:00 am -
2 stops48h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/277:15 am -
2 stops25h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:00 am -
2 stops24h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Multiple Airlines logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/22:41 am -
2 stops22h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/162:41 am -
3 stops34h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:15 am -
2 stops25h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:15 am -
2 stops25h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:04 am -
2 stops48h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Multiple Airlines logo]()
$306
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 September 29, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $401 (Booking.com) |
One-way from | $234 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $502 |
Good round-trip deal | $507 or less |
Good one-way deal | $410 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 7,457,451 searches. Data last updated September 29, 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 Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Sat 11/21
1:24 am-11:59 pm
1 stop22h 35m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$344
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Thu 10/15
6:00 am-9:10 pm
3 stops40h 10m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$353
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Wed 12/2
5:58 pm-10:30 pm
2 stops28h 32m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$356
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Wed 10/28
8:45 am-10:30 pm
1 stop14h 45m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$406
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Mon 11/2
2:13 pm-9:07 am
1 stop18h 54m
San José Juan Santamaria Intl
Thu 11/12
10:03 am-12:11 am
1 stop14h 08m
$406
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Mon 11/23
2:13 pm-9:07 am
1 stop18h 54m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$411
Quickest round-trip
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Sat 12/5
3:00 pm-10:17 pm
1 stop7h 17m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$415
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Tue 10/13
5:27 am-12:00 pm
1 stop7h 33m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$415
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Sat 12/26
1:24 am-11:59 pm
1 stop22h 35m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$433
ChicagoSan José
ORD Chicago O'Hare Intl - SJO San José Juan Santamaria Intl
ORDSJO
Chicago O'Hare Intl
Wed 11/25
2:13 pm-12:19 pm
1 stop22h 06m
San José Juan Santamaria Intl
Wed 12/2
5:35 am-12:11 am
1 stop18h 36m
$473
Showing 1-10 of 19 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 September.
| 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 Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-San José flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Chicago O'Hare Intl Airport-San José flight deals on Cheapflights vs. Ovago >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 Ovago the most. Ovago 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
Prices
Delays
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 $483). Flying from Chicago O'Hare Intl Airport to San José in December is currently the most expensive (average of $648). 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.
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to San José?
Airfare is below average for this route at the moment.
Chicago O'Hare Intl Airport to San José flights typically cost between $429 and $617 in October.The cheapest round-trip price found within the last 5 days was $401 on Copa Airlines (Oct 31-Nov 7).
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 151 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 15% of flights being delayed.
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 September 29, 2026.
See what other customers who have flown with Copa Airlines,United Airlines, andAir Canada 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.
Overall
7.6
Comfort
7.4
Crew
8.1
Entertainment
6.9
Boarding
7.8
Food
6.9
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
Overall
7.6
Comfort
7.4
Crew
8.1
Entertainment
6.9
Boarding
7.8
Food
6.9
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
Overall
7.6
Comfort
7.4
Crew
8.1
Entertainment
6.9
Boarding
7.8
Food
6.9
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
Overall
7.6
Comfort
7.4
Crew
8.1
Entertainment
6.9
Boarding
7.8
Food
6.9
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
Overall
7.6
Comfort
7.4
Crew
8.1
Entertainment
6.9
Boarding
7.8
Food
6.9
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
Overall
7.6
Comfort
7.4
Crew
8.1
Entertainment
6.9
Boarding
7.8
Food
6.9
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - 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
Jacó
Heredia
Dominical
Manuel Antonio
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from O'Hare Intl
Popular flights
San José flight routes
Alternative routes for O'Hare Intl to San José
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to San José by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from O'Hare Intl to San José by cabin class
Find flights from O'Hare Intl to San José, based on your preferred cabin class, be it economy, premium economy, business, or first class.
O'Hare Intl and San José flights
Browse other O'Hare Intl and San José flight options. Last updated on September 29, 2026.
Other flights from O'Hare Intl
Browse through other flights departing from O'Hare Intl. Flights are based on user searches made on Cheapflights and were last updated on September 29, 2026.
Popular flight searches
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 September 29, 2026.
Top 9 airlines flying from O'Hare Intl to San José
Discover the top 9 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 7,457,451 searches. Data last updated September 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$565 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$303 | Average$516 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$324 | Average$642 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$333 | Average$538 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$364 | Average$482 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$382 | Average$602 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$384 | Average$740 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$390 | Average$598 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$395 | Average$484 | FlexibilityNo cancel fee | On-time63% |