$218+ Cheap flights from San José (SJO) to O'Hare Intl (ORD)
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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — ORD
Nov 19 — Nov 261
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 January or February, booked 63 days in advance, depart on a Tuesday or Friday 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 October 20, 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 October 20, 2026.
This United Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/271:25 pm -
Nonstop5h 32m
Thu 1/77:25 am -
1 stop10h 51m
Deal found 10/16![United Airlines logo]()
$403
This Avianca deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/199:25 am -
1 stop10h 55m
Wed 10/2811:30 pm -
1 stop10h 20m
Deal found 10/15![Avianca logo]()
$404
This Avianca deal was found by Cheapflights users on 10/19. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/239:30 am -
1 stop11h 00m
Wed 12/210:30 pm -
1 stop17h 50m
Deal found 10/19![Avianca logo]()
$405
This Copa Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/93:59 am -
1 stop8h 47m
Sat 11/142:13 pm -
1 stop16h 49m
Deal found 10/16![Copa Airlines logo]()
$406
This United Airlines deal was found by Cheapflights users on 10/17. 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 11/141:55 pm -
Nonstop5h 33m
Sat 11/285:30 am -
1 stop15h 09m
Deal found 10/17![United Airlines logo]()
$408
This United Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/269:05 am -
1 stop14h 34m
Mon 1/47:00 am -
1 stop15h 32m
Deal found 10/16![United Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 10/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/213:52 pm -
1 stop8h 56m
Sat 11/286:00 am -
1 stop8h 51m
Deal found 10/19![American Airlines logo]()
$410
This Kissandfly.com deal was found by Cheapflights users on 10/19. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/211:55 pm -
Nonstop5h 33m
Sat 11/287:17 am -
Nonstop5h 18m
Deal found 10/19![Lufthansa logo]()
$411
This United Airlines deal was found by Cheapflights users on 10/19. 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 12/221:15 am -
1 stop8h 55m
Sun 1/107:02 am -
Nonstop5h 13m
Deal found 10/19![United Airlines logo]()
$413
This Avianca deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/285:35 am -
1 stop7h 20m
Sat 1/22:20 pm -
1 stop18h 15m
Deal found 10/15![Avianca logo]()
$414
This deal was found by Cheapflights users on 10/18. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2012:35 pm -
1 stop10h 51m
Sat 11/2812:01 am -
1 stop11h 24m
Deal found 10/18![United Airlines logo]()
$415
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 October 20, 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 October 20, 2026.
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Wed 1/131:15 am -
1 stop15h 10m
Sun 1/247:02 am -
Nonstop5h 13m
Deal found 10/19![United Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 10/17. 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 12/217:00 am -
1 stop16h 59m
Thu 12/316:00 am -
1 stop15h 46m
Deal found 10/17![Delta logo]()
$409
This United Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/261:25 pm -
Nonstop5h 32m
Wed 12/309:43 pm -
1 stop24h 49m
Deal found 10/16![United Airlines logo]()
$422
This United Airlines deal was found by Cheapflights users on 10/17. 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 1/131:25 pm -
Nonstop5h 32m
Wed 1/205:30 am -
1 stop7h 52m
Deal found 10/17![United Airlines logo]()
$426
This United Airlines deal was found by Cheapflights users on 10/17. 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 12/191:25 pm -
Nonstop5h 32m
Wed 12/309:43 pm -
1 stop24h 49m
Deal found 10/17![United Airlines logo]()
$427
This United Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/261:25 pm -
Nonstop5h 32m
Thu 1/77:25 am -
1 stop10h 51m
Deal found 10/16![United Airlines logo]()
$429
This United Airlines deal was found by Cheapflights users on 10/17. 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.
Thu 11/511:28 pm -
1 stop14h 26m
Mon 11/95:30 am -
1 stop7h 52m
Deal found 10/17![United Airlines logo]()
$502
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Sun 11/156:40 am -
1 stop29h 35m
Sun 11/229:35 pm -
1 stop23h 04m
Deal found 10/19![United Airlines logo]()
$504
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Wed 12/231:25 pm -
Nonstop5h 32m
Fri 1/17:02 am -
Nonstop5h 13m
Deal found 10/19![United Airlines logo]()
$555
Last-minute flights from San José to O'Hare IntlDiscover last-minute flight deals from San José to O'Hare Intl. Data last updated October 20, 2026 and is based on user searches.
Discover last-minute flight deals from San José to O'Hare Intl. Data last updated October 20, 2026 and is based on user searches.
This Avianca deal was found by Cheapflights users on 10/19. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/209:25 am -
1 stop10h 55m
Mon 10/2611:30 pm -
1 stop17h 50m
Deal found 10/19![Avianca logo]()
$403
This Avianca deal was found by Cheapflights users on 10/19. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:25 am -
1 stop10h 55m
Wed 10/2111:20 pm -
1 stop10h 30m
Deal found 10/19![Avianca logo]()
$404
This Copa Airlines deal was found by Cheapflights users on 10/18. 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.
Tue 11/105:55 pm -
1 stop18h 51m
Sat 11/142:13 pm -
1 stop18h 06m
Deal found 10/18![Copa Airlines logo]()
$406
This United Airlines deal was found by Cheapflights users on 10/17. 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 11/141:55 pm -
Nonstop5h 33m
Sat 11/285:30 am -
1 stop15h 09m
Deal found 10/17![United Airlines logo]()
$408
This deal was found by Cheapflights users on 10/18. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2012:35 pm -
1 stop10h 51m
Sat 11/2812:01 am -
1 stop11h 24m
Deal found 10/18![United Airlines logo]()
$415
This American Airlines deal was found by Cheapflights users on 10/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:07 pm -
1 stop18h 53m
Sun 11/295:00 am -
1 stop8h 46m
Deal found 10/20![American Airlines logo]()
$418
This American Airlines deal was found by Cheapflights users on 10/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/213:52 pm -
1 stop8h 56m
Sat 11/286:00 am -
1 stop8h 51m
Deal found 10/19![American Airlines logo]()
$410
This Kissandfly.com deal was found by Cheapflights users on 10/19. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/211:55 pm -
Nonstop5h 33m
Sat 11/287:17 am -
Nonstop5h 18m
Deal found 10/19![Lufthansa logo]()
$411
This Avianca deal was found by Cheapflights users on 10/19. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/239:30 am -
1 stop11h 00m
Wed 12/210:30 pm -
1 stop17h 50m
Deal found 10/19![Avianca logo]()
$405
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Mon 11/232:25 pm -
1 stop10h 20m
Sat 11/285:30 am -
1 stop15h 09m
Deal found 10/19![United Airlines logo]()
$409
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 October 20, 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 October 20, 2026.
This Mytrip deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:00 am -
2 stops15h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Multiple Airlines logo]()
$218
This CheapOair deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:15 pm -
1 stop18h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$237
This Volaris deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/243:00 pm -
1 stop20h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$239
This Booking.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/14:15 pm -
1 stop18h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/102:30 am -
1 stop20h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Viva logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/172:30 am -
1 stop20h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Viva logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/86:53 am -
1 stop21h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/175:53 pm -
3 stops24h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$306
This Expedia deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:45 am -
1 stop30h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Air Canada logo]()
$315
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 October 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $403 (United Airlines) |
One-way from | $218 (Mytrip) |
Popular in | July |
Cheapest in | January |
Average price | $507 |
Good round-trip deal | $408 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 7,457,451 searches. Data last updated October 20, 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 San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Thu 12/24
3:00 pm-11:13 am
1 stop20h 13m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$239
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Thu 11/5
2:40 am-10:55 pm
1 stop20h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$328
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Thu 11/26
2:40 am-10:55 pm
1 stop20h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$362
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sat 11/14
9:20 am-7:52 pm
1 stop10h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$367
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Wed 1/13
1:15 am-4:25 pm
1 stop15h 10m
Chicago O'Hare Intl
Sun 1/24
7:02 am-12:15 pm
Nonstop5h 13m
$409
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Mon 12/21
7:00 am-11:59 pm
1 stop16h 59m
Chicago O'Hare Intl
Thu 12/31
6:00 am-9:46 pm
1 stop15h 46m
$409
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sat 12/26
1:25 pm-6:57 pm
Nonstop5h 32m
Chicago O'Hare Intl
Wed 12/30
9:43 pm-10:32 pm
1 stop24h 49m
$422
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Wed 1/13
1:25 pm-6:57 pm
Nonstop5h 32m
Chicago O'Hare Intl
Wed 1/20
5:30 am-1:22 pm
1 stop7h 52m
$426
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sat 12/19
1:25 pm-6:57 pm
Nonstop5h 32m
Chicago O'Hare Intl
Wed 12/30
9:43 pm-10:32 pm
1 stop24h 49m
$427
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sat 12/26
1:25 pm-6:57 pm
Nonstop5h 32m
Chicago O'Hare Intl
Thu 1/7
7:25 am-6:16 pm
1 stop10h 51m
$429
Showing 1-10 of 19 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 October.
| 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 62 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, January 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 July is currently the most expensive (average of $643). 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 San José to Chicago O'Hare Intl Airport?
Airfare is typical for this route at the moment.
San José to Chicago O'Hare Intl Airport flights typically cost between $385 and $572 in December.The cheapest round-trip price found within the last 5 days was $403 on United Airlines (Dec 27-Jan 4).
How often are flights from San José to Chicago delayed?
About 5% of weekly flights between San José and Chicago have experienced delays in the past year, with the average delay time being 239 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 October 20, 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.
Comfort
7.5
Crew
8.1
Food
7.0
Entertainment
6.9
Overall
7.6
Boarding
7.8
Reviews
1 / 20
4.0
OkayPaul,Jun 2025
PTY - MIA
Comfort
7.5
Crew
8.1
Food
7.0
Entertainment
6.9
Overall
7.6
Boarding
7.8
Reviews
1 / 20
4.0
OkayPaul,Jun 2025
PTY - MIA
Comfort
7.5
Crew
8.1
Food
7.0
Entertainment
6.9
Overall
7.6
Boarding
7.8
Reviews
1 / 20
4.0
OkayPaul,Jun 2025
PTY - MIA
Comfort
7.5
Crew
8.1
Food
7.0
Entertainment
6.9
Overall
7.6
Boarding
7.8
Reviews
1 / 20
4.0
OkayPaul,Jun 2025
PTY - MIA
Comfort
7.5
Crew
8.1
Food
7.0
Entertainment
6.9
Overall
7.6
Boarding
7.8
Reviews
1 / 20
4.0
OkayPaul,Jun 2025
PTY - MIA
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
Naperville
Lake Geneva
Des Plaines
Glenview
Schaumburg
Oak Brook
Oakbrook Terrace
Delavan
Aurora
Libertyville
Rockford
Hoffman Estates
Beloit
Orland Park
South Holland
Elgin
Racine
Janesville
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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 7,457,451 searches. Data last updated October 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$189 | Average$488 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$341 | Average$519 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$360 | Average$492 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$382 | Average$474 | FlexibilityNo cancel fee | On-time71% |