$158+ 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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — ORD
Sep 20 — Sep 271
Round-trip
1 adult, Economy
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Find cheap flights from San José to O'Hare Intl with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from San José Juan Santamaria Intl to Chicago O'Hare Intl are usually found in February or January, booked 90 days in advance, depart on a Friday or Tuesday 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 August 21, 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 August 21, 2026.
This United Airlines deal was found by Cheapflights users on 8/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/241:25 pm -
Nonstop5h 32m
Sun 1/35:30 am -
1 stop17h 02m
Deal found 8/21![United Airlines logo]()
$365
This United Airlines deal was found by Cheapflights users on 8/17. 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.
Mon 12/2112:35 pm -
1 stop9h 00m
Tue 12/2910:00 pm -
1 stop24h 00m
Deal found 8/17![United Airlines logo]()
$366
This United Airlines deal was found by Cheapflights users on 8/17. 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 12/231:15 am -
1 stop13h 39m
Thu 12/317:02 am -
Nonstop5h 13m
Deal found 8/17![United Airlines logo]()
$371
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:01 pm -
1 stop15h 46m
Tue 10/135:00 am -
1 stop10h 00m
Deal found 8/17![American Airlines logo]()
$375
This Flightnetwork deal was found by Cheapflights users on 8/16. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3010:03 am -
1 stop13h 59m
Wed 10/73:20 pm -
1 stop18h 44m
Deal found 8/16![Copa Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:00 am -
2 stops13h 06m
Wed 10/149:30 pm -
1 stop17h 30m
Deal found 8/17![American Airlines logo]()
$380
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Wed 10/143:01 pm -
1 stop19h 09m
Tue 10/2011:00 am -
2 stops10h 21m
Deal found 8/19![American Airlines logo]()
$386
This American Airlines deal was found by Cheapflights users on 8/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:00 am -
2 stops13h 02m
Tue 10/136:00 am -
1 stop9h 00m
Deal found 8/18![American Airlines logo]()
$387
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 August 21, 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 August 21, 2026.
This United Airlines deal was found by Cheapflights users on 8/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/191:15 am -
1 stop8h 10m
Sat 1/303:51 pm -
1 stop14h 34m
Deal found 8/20![United Airlines logo]()
$366
This Copa Airlines deal was found by Cheapflights users on 8/18. 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.
Wed 9/2310:03 am -
1 stop13h 59m
Sun 9/273:20 pm -
1 stop16h 50m
Deal found 8/18![Copa Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 8/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/141:25 pm -
1 stop9h 32m
Sun 10/185:27 am -
1 stop7h 33m
Deal found 8/18![Delta logo]()
$402
This United Airlines deal was found by Cheapflights users on 8/19. 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 11/1611:28 pm -
1 stop10h 17m
Fri 12/49:25 am -
1 stop11h 14m
Deal found 8/19![United Airlines logo]()
$366
This Copa Airlines deal was found by Cheapflights users on 8/20. 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 11/53:59 am -
1 stop20h 12m
Sat 11/142:13 pm -
1 stop16h 49m
Deal found 8/20![Copa Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 8/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/117:00 am -
1 stop12h 02m
Mon 12/145:30 am -
1 stop7h 35m
Deal found 8/18![Delta logo]()
$402
This United Airlines deal was found by Cheapflights users on 8/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/251:25 pm -
Nonstop5h 32m
Sat 1/29:43 pm -
1 stop24h 49m
Deal found 8/18![United Airlines logo]()
$366
This Copa Airlines deal was found by Cheapflights users on 8/16. 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.
Sun 9/2710:03 am -
1 stop13h 59m
Sat 10/33:20 pm -
1 stop16h 50m
Deal found 8/16![Copa Airlines logo]()
$398
This United Airlines deal was found by Cheapflights users on 8/17. 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.
Tue 12/291:15 am -
1 stop18h 43m
Sun 1/107:45 am -
1 stop12h 54m
Deal found 8/17![United Airlines logo]()
$375
This United Airlines deal was found by Cheapflights users on 8/17. 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 10/37:55 am -
1 stop9h 35m
Sun 10/116:25 am -
1 stop14h 12m
Deal found 8/17![United Airlines logo]()
$375
Last-minute flights from San José to O'Hare IntlDiscover last-minute flight deals from San José to O'Hare Intl. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from San José to O'Hare Intl. Data last updated August 21, 2026 and is based on user searches.
This Copa Airlines deal was found by Cheapflights users on 8/18. 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 9/34:08 am -
1 stop19h 54m
Tue 9/88:01 am -
1 stop24h 09m
Deal found 8/18![Copa Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 8/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:07 pm -
1 stop18h 38m
Sun 9/68:53 pm -
1 stop16h 33m
Deal found 8/16![American Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 8/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:19 pm -
2 stops17h 37m
Mon 9/215:30 am -
1 stop7h 24m
Deal found 8/18![Delta logo]()
$402
This United Airlines deal was found by Cheapflights users on 8/19. 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.
Fri 9/181:25 pm -
1 stop9h 02m
Mon 9/289:38 pm -
1 stop15h 43m
Deal found 8/19![United Airlines logo]()
$366
This United Airlines deal was found by Cheapflights users on 8/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:55 am -
1 stop15h 28m
Mon 9/289:35 pm -
1 stop15h 03m
Deal found 8/18![United Airlines logo]()
$375
This American Airlines deal was found by Cheapflights users on 8/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/261:00 pm -
1 stop20h 08m
Sun 10/49:15 pm -
1 stop17h 45m
Deal found 8/16![American Airlines logo]()
$384
This Faresmojo deal was found by Cheapflights users on 8/16. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/264:08 am -
1 stop19h 54m
Sat 10/33:20 pm -
1 stop18h 44m
Deal found 8/16![Copa Airlines logo]()
$391
This American Airlines deal was found by Cheapflights users on 8/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/271:00 pm -
1 stop20h 08m
Sun 10/49:15 pm -
1 stop17h 45m
Deal found 8/18![American Airlines logo]()
$388
This Copa Airlines deal was found by Cheapflights users on 8/17. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2710:03 am -
1 stop13h 59m
Sat 10/108:01 am -
1 stop24h 09m
Deal found 8/17![Copa Airlines logo]()
$398
This Flightnetwork deal was found by Cheapflights users on 8/16. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3010:03 am -
1 stop13h 59m
Wed 10/73:20 pm -
1 stop18h 44m
Deal found 8/16![Copa Airlines logo]()
$379
This Copa Airlines deal was found by Cheapflights users on 8/18. 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.
Wed 9/3010:03 am -
1 stop13h 59m
Sat 10/103:20 pm -
1 stop16h 50m
Deal found 8/18![Copa Airlines logo]()
$381
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 August 21, 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 August 21, 2026.
This Viva deal was found by Cheapflights users on 8/19. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:25 am -
1 stop20h 30m
Deal found 8/19![Viva logo]()
$158
This Viva deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:15 pm -
1 stop22h 55m
Deal found 8/20![Viva logo]()
$200
This Viva deal was found by Cheapflights users on 8/16. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/102:25 am -
1 stop20h 35m
Deal found 8/16![Viva logo]()
$209
This Volaris deal was found by Cheapflights users on 8/18. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/244:15 pm -
1 stop18h 53m
Deal found 8/18![Multiple Airlines logo]()
$216
This Volaris deal was found by Cheapflights users on 8/17. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/314:15 pm -
1 stop18h 53m
Deal found 8/17![Multiple Airlines logo]()
$223
This Viva deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/262:25 am -
1 stop20h 30m
Deal found 8/20![Viva logo]()
$234
This Volaris deal was found by Cheapflights users on 8/17. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/44:15 pm -
1 stop18h 54m
Deal found 8/17![Multiple Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/32:25 am -
1 stop20h 35m
Deal found 8/16![Viva logo]()
$247
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/134:15 pm -
1 stop18h 54m
Deal found 8/17![Multiple Airlines logo]()
$254
This FlightHub deal was found by Cheapflights users on 8/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:45 am -
1 stop20h 46m
Deal found 8/18![Frontier logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:55 am -
2 stops38h 29m
Deal found 8/17![Multiple Airlines logo]()
$257
This JetBlue deal was found by Cheapflights users on 8/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/93:05 pm -
1 stop8h 23m
Deal found 8/16![JetBlue logo]()
$260
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 August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $365 (United Airlines) |
One-way from | $158 (Viva) |
Popular in | July |
Cheapest in | February |
Average price | $523 |
Good round-trip deal | $497 or less |
Good one-way deal | $264 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 August 21, 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
Tue 1/19
1:15 am-9:25 am
1 stop8h 10m
Chicago O'Hare Intl
Sat 1/30
3:51 pm-6:25 am
1 stop14h 34m
$366
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Mon 11/16
11:28 pm-9:45 am
1 stop10h 17m
Chicago O'Hare Intl
Fri 12/4
9:25 am-8:39 pm
1 stop11h 14m
$366
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Fri 12/25
1:25 pm-6:57 pm
Nonstop5h 32m
Chicago O'Hare Intl
Sat 1/2
9:43 pm-10:32 pm
1 stop24h 49m
$366
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Tue 12/29
1:15 am-7:58 pm
1 stop18h 43m
Chicago O'Hare Intl
Sun 1/10
7:45 am-8:39 pm
1 stop12h 54m
$375
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sat 10/3
7:55 am-6:30 pm
1 stop9h 35m
Chicago O'Hare Intl
Sun 10/11
6:25 am-7:37 pm
1 stop14h 12m
$375
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Wed 9/23
10:03 am-1:02 am
1 stop13h 59m
Chicago O'Hare Intl
Sun 9/27
3:20 pm-7:10 am
1 stop16h 50m
$381
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Thu 11/5
3:59 am-12:11 am
1 stop20h 12m
Chicago O'Hare Intl
Sat 11/14
2:13 pm-7:02 am
1 stop16h 49m
$381
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sun 9/27
10:03 am-1:02 am
1 stop13h 59m
Chicago O'Hare Intl
Sat 10/3
3:20 pm-7:10 am
1 stop16h 50m
$398
Quickest round-trip
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Wed 10/14
1:25 pm-11:57 pm
1 stop9h 32m
Chicago O'Hare Intl
Sun 10/18
5:27 am-12:00 pm
1 stop7h 33m
$402
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Fri 12/11
7:00 am-7:02 pm
1 stop12h 02m
Chicago O'Hare Intl
Mon 12/14
5:30 am-1:05 pm
1 stop7h 35m
$402
Showing 1-10 of 20 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 August.
| 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 $393). 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 below average for this route at the moment.
San José to Chicago O'Hare Intl Airport flights typically cost between $405 and $588 in December.The cheapest round-trip price found within the last 5 days was $365 on United Airlines (Dec 24-Jan 3).
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 254 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 August 21, 2026.
See what other customers who have flown with Copa Airlines,United Airlines, andAmerican Airlines from San José to Chicago O'Hare Intl Airport have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.8
Food
6.9
Entertainment
6.8
Overall
7.6
Comfort
7.4
Crew
8.1
Reviews
1 / 20
4.0
OkayPaul,Jun 2025
PTY - MIA
Boarding
7.8
Food
6.9
Entertainment
6.8
Overall
7.6
Comfort
7.4
Crew
8.1
Reviews
1 / 20
4.0
OkayPaul,Jun 2025
PTY - MIA
Boarding
7.8
Food
6.9
Entertainment
6.8
Overall
7.6
Comfort
7.4
Crew
8.1
Reviews
1 / 20
4.0
OkayPaul,Jun 2025
PTY - MIA
Boarding
7.8
Food
6.9
Entertainment
6.8
Overall
7.6
Comfort
7.4
Crew
8.1
Reviews
1 / 20
4.0
OkayPaul,Jun 2025
PTY - MIA
Boarding
7.8
Food
6.9
Entertainment
6.8
Overall
7.6
Comfort
7.4
Crew
8.1
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
Schaumburg
Naperville
Lake Geneva
Oak Brook
Oakbrook Terrace
Delavan
South Holland
Libertyville
Gurnee
Orland Park
Hoffman Estates
Aurora
Beloit
Rockford
Racine
Great Lakes
Janesville
Joliet
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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 August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$189 | Average$451 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$332 | Average$518 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$370 | Average$492 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$375 | Average$636 | FlexibilityNo cancel fee | On-time71% |