$222+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — ORD
Jul 23 — Jul 301
Round-trip
1 adult, Economy
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1. Tell us where you want to go
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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
Cheapest
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 June 23, 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 June 23, 2026.
This SmartFares deal was found by Cheapflights users on 6/23. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Sun 8/307:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 6/23![JetBlue logo]()
$386
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 Cheapflightsfares 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 6/19![JetBlue logo]()
$393
This SmartFares deal was found by Cheapflights users on 6/21. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Mon 8/317:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 6/21![JetBlue logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:07 am
SJO
- ORD
1 stop15h 48m
Multiple Airlines
Tue 10/139:33 pm
ORD
- SJO
2 stops18h 38m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$420
This Travelocity deal was found by Cheapflights users on 6/22. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:35 am
SJO
- ORD
1 stop12h 35m
Multiple Airlines
Fri 8/217:00 am
ORD
- SJO
1 stop6h 57m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$431
This Volaris deal was found by Cheapflights users on 6/23. 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 6/23![Multiple Airlines logo]()
$434
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:07 am
SJO
- ORD
1 stop15h 48m
Multiple Airlines
Wed 10/147:00 am
ORD
- SJO
2 stops33h 11m
Multiple Airlines
Deal found 6/18![Multiple Airlines 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 June 23, 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 June 23, 2026.
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:05 pm
SJO
- ORD
Nonstop5h 33m
United Airlines
Sat 11/73:40 pm
ORD
- SJO
1 stop14h 45m
United Airlines
Deal found 6/19![United Airlines logo]()
$491
This Copa Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:45 am
SJO
- ORD
1 stop18h 17m
Copa Airlines
Sun 9/273:20 pm
ORD
- SJO
1 stop18h 44m
Copa Airlines
Deal found 6/18![Copa Airlines logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 6/21. 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 10/273:58 am
SJO
- ORD
1 stop20h 07m
Copa Airlines
Thu 11/52:13 pm
ORD
- SJO
1 stop18h 54m
Copa Airlines
Deal found 6/21![Copa Airlines logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 6/22. 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.
Mon 8/174:08 am
SJO
- ORD
1 stop19h 54m
Copa Airlines
Fri 9/253:20 pm
ORD
- SJO
1 stop20h 38m
Copa Airlines
Deal found 6/22![Copa Airlines logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 6/20. 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.
Fri 10/308:30 am
SJO
- ORD
1 stop15h 35m
Copa Airlines
Sun 11/82:13 pm
ORD
- SJO
1 stop20h 46m
Copa Airlines
Deal found 6/20![Copa Airlines logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 6/20. 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.
Wed 9/162:48 pm
SJO
- ORD
1 stop9h 14m
Copa Airlines
Mon 9/213:20 pm
ORD
- SJO
1 stop16h 50m
Copa Airlines
Deal found 6/20![Copa Airlines logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 6/20. 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.
Thu 11/195:55 pm
SJO
- ORD
1 stop18h 51m
Copa Airlines
Wed 11/252:13 pm
ORD
- SJO
1 stop18h 54m
Copa Airlines
Deal found 6/20![Copa Airlines logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 6/22. 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 8/110:03 am
SJO
- ORD
1 stop12h 59m
Copa Airlines
Fri 8/143:21 pm
ORD
- SJO
1 stop18h 43m
Copa Airlines
Deal found 6/22![Copa Airlines logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 6/21. 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.
Sat 9/264:08 am
SJO
- ORD
1 stop19h 54m
Copa Airlines
Sun 10/48:01 am
ORD
- SJO
1 stop24h 09m
Copa Airlines
Deal found 6/21![Copa Airlines logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:03 am
SJO
- ORD
1 stop13h 59m
Copa Airlines
Sat 9/193:20 pm
ORD
- SJO
1 stop16h 50m
Copa Airlines
Deal found 6/18![Copa Airlines logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 6/23. 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 8/254:08 am
SJO
- ORD
1 stop19h 54m
Copa Airlines
Sun 8/303:21 pm
ORD
- SJO
1 stop20h 37m
Copa Airlines
Deal found 6/23![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 June 23, 2026 and is based on user searches.
Discover last-minute flight deals from San José to O'Hare Intl. Data last updated June 23, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 6/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/74:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Tue 8/251:49 pm
ORD
- SJO
1 stop11h 10m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$453
This KAYAK deal was found by Cheapflights users on 6/20. 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 7/71:50 pm
SJO
- ORD
1 stop18h 00m
JetBlue
Tue 9/17:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 6/20![JetBlue logo]()
$475
This Justfly.com deal was found by Cheapflights users on 6/21. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/103:10 pm
SJO
- ORD
1 stop23h 45m
Avianca
Tue 7/148:40 am
ORD
- SJO
2 stops24h 50m
Avianca
Deal found 6/21![Avianca logo]()
$477
This Justfly.com deal was found by Cheapflights users on 6/19. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/115:05 am
SJO
- ORD
1 stop9h 50m
Avianca
Tue 7/148:40 am
ORD
- SJO
2 stops24h 50m
Avianca
Deal found 6/19![Avianca logo]()
$460
This CheapOair deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/172:02 pm
SJO
- ORD
1 stop8h 42m
Multiple Airlines
Fri 7/315:13 pm
ORD
- SJO
1 stop16h 17m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$488
This Expedia deal was found by Cheapflights users on 6/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:45 am
SJO
- ORD
1 stop12h 25m
Frontier
Sat 7/255:13 pm
ORD
- SJO
1 stop16h 07m
Frontier
Deal found 6/19![Frontier logo]()
$496
This Avianca deal was found by Cheapflights users on 6/21. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:45 pm
SJO
- ORD
2 stops10h 42m
Avianca
Sat 7/255:15 pm
ORD
- SJO
1 stop7h 25m
Avianca
Deal found 6/21![Avianca logo]()
$454
This eDestinos deal was found by Cheapflights users on 6/21. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/214:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Sun 7/261:49 pm
ORD
- SJO
1 stop11h 10m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$465
This Copa Airlines deal was found by Cheapflights users on 6/23. 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 7/214:08 am
SJO
- ORD
1 stop8h 49m
Copa Airlines
Sun 7/263:21 pm
ORD
- SJO
1 stop17h 05m
Copa Airlines
Deal found 6/23![Copa Airlines logo]()
$494
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:15 am
SJO
- ORD
1 stop12h 45m
United Airlines
Wed 7/299:40 pm
ORD
- SJO
1 stop13h 31m
United Airlines
Deal found 6/19![United Airlines logo]()
$497
This FlightHub deal was found by Cheapflights users on 6/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:05 am
SJO
- ORD
1 stop9h 50m
Avianca
Tue 7/288:40 am
ORD
- SJO
2 stops24h 50m
Avianca
Deal found 6/19![Avianca logo]()
$491
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 June 23, 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 June 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:07 am
SJO
- ORD
1 stop15h 48m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$222
This SmartFares deal was found by Cheapflights users on 6/21. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:05 pm
SJO
- ORD
1 stop9h 26m
JetBlue
Deal found 6/21![JetBlue logo]()
$231
This Cheapflightsfares deal was found by Cheapflights users on 6/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/232:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Deal found 6/21![JetBlue logo]()
$238
This Volaris deal was found by Cheapflights users on 6/22. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/34:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$242
This Volaris deal was found by Cheapflights users on 6/22. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/14:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$263
This Viva deal was found by Cheapflights users on 6/23. 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 6/23![Viva logo]()
$266
This Orbitz deal was found by Cheapflights users on 6/20. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/29:35 am
SJO
- ORD
1 stop12h 35m
Frontier
Deal found 6/20![Frontier logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/117:07 am
SJO
- ORD
1 stop15h 03m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$268
This deal was found by Cheapflights users on 6/22. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/309:35 am
SJO
- ORD
1 stop12h 35m
Frontier
Deal found 6/22![Frontier logo]()
$270
This Mytrip deal was found by Cheapflights users on 6/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/74:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$271
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 June 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $386 (SmartFares) |
One-way from | $222 (Kiwi.com) |
Popular in | July |
Cheapest in | February |
Average price | $539 |
Good round-trip deal | $701 or less |
Good one-way deal | $353 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 June 23, 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
Quickest round-trip
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 10/31
1:05 pm-7:38 pm
Nonstop5h 33m
Chicago O'Hare Intl
Sat 11/7
3:40 pm-6:25 am
1 stop14h 45m
$491
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 9/24
5:45 am-1:02 am
1 stop18h 17m
Chicago O'Hare Intl
Sun 9/27
3:20 pm-9:04 am
1 stop18h 44m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 10/27
3:58 am-1:05 am
1 stop20h 07m
Chicago O'Hare Intl
Thu 11/5
2:13 pm-9:07 am
1 stop18h 54m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Mon 8/17
4:08 am-1:02 am
1 stop19h 54m
Chicago O'Hare Intl
Fri 9/25
3:20 pm-10:58 am
1 stop20h 38m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Fri 10/30
8:30 am-1:05 am
1 stop15h 35m
Chicago O'Hare Intl
Sun 11/8
2:13 pm-10:59 am
1 stop20h 46m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 9/16
2:48 pm-1:02 am
1 stop9h 14m
Chicago O'Hare Intl
Mon 9/21
3:20 pm-7:10 am
1 stop16h 50m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 11/19
5:55 pm-12:46 pm
1 stop18h 51m
Chicago O'Hare Intl
Wed 11/25
2:13 pm-9:07 am
1 stop18h 54m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 8/1
10:03 am-12:02 am
1 stop12h 59m
Chicago O'Hare Intl
Fri 8/14
3:21 pm-9:04 am
1 stop18h 43m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 9/26
4:08 am-1:02 am
1 stop19h 54m
Chicago O'Hare Intl
Sun 10/4
8:01 am-7:10 am
1 stop24h 09m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Mon 9/14
10:03 am-1:02 am
1 stop13h 59m
Chicago O'Hare Intl
Sat 9/19
3:20 pm-7:10 am
1 stop16h 50m
$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 June.
| 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 $389). Flying from San José to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $633). 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 June 23, 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 243 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 5% 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 June 23, 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.
Food
6.9
Comfort
7.4
Crew
8.1
Entertainment
6.8
Boarding
7.8
Overall
7.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Food
6.9
Comfort
7.4
Crew
8.1
Entertainment
6.8
Boarding
7.8
Overall
7.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Food
6.9
Comfort
7.4
Crew
8.1
Entertainment
6.8
Boarding
7.8
Overall
7.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Food
6.9
Comfort
7.4
Crew
8.1
Entertainment
6.8
Boarding
7.8
Overall
7.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Food
6.9
Comfort
7.4
Crew
8.1
Entertainment
6.8
Boarding
7.8
Overall
7.6
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 locationsBenton Harbor
Rosemont
Schaumburg
Naperville
Lake Geneva
Gurnee
Delavan
Oakbrook Terrace
Downers Grove
Des Plaines
Oak Brook
South Holland
Libertyville
Hoffman Estates
Warrenville
Rockford
Racine
Great Lakes
Northbrook
Waukegan
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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 June 23, 2026.
San José and O'Hare Intl flights
Browse other San José and O'Hare Intl flight options. Last updated on June 23, 2026.
Other flights from San José
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Top 4 airlines flying from San José to O'Hare Intl
Discover the top 4 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 June 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$189 | Average$493 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$332 | Average$513 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$367 | Average$633 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$370 | Average$472 | FlexibilityNo cancel fee | On-time69% |