$164+ 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 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — ORD
Sep 6 — Sep 131
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 7, 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 7, 2026.
This Copa Airlines deal was found by Cheapflights users on 8/7. 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 10/910:03 am -
1 stop26h 56m
Wed 10/143:20 pm -
1 stop18h 44m
Deal found 8/7![Copa Airlines logo]()
$379
This Copa Airlines deal was found by Cheapflights users on 8/4. 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 10/263:58 am -
1 stop20h 07m
Fri 11/62:13 pm -
1 stop20h 46m
Deal found 8/4![Copa Airlines logo]()
$381
This Copa Airlines deal was found by Cheapflights users on 8/3. 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 -
1 stop13h 59m
Sat 9/193:20 pm -
1 stop16h 50m
Deal found 8/3![Copa Airlines logo]()
$392
This Copa Airlines deal was found by Cheapflights users on 8/4. 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 9/2510:03 am -
1 stop26h 56m
Thu 10/18:01 am -
1 stop24h 09m
Deal found 8/4![Copa Airlines logo]()
$397
This Copa Airlines deal was found by Cheapflights users on 8/7. 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 12/229:59 am -
1 stop14h 12m
Tue 1/52:13 pm -
1 stop16h 49m
Deal found 8/7![Copa Airlines logo]()
$398
This Copa Airlines deal was found by Cheapflights users on 8/2. 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 10/95:55 pm -
1 stop19h 04m
Sat 10/173:20 pm -
1 stop17h 59m
Deal found 8/2![Copa Airlines logo]()
$408
This Booking.com deal was found by Cheapflights users on 8/2. 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.
Fri 8/216:17 pm -
1 stop29h 45m
Fri 8/283:21 pm -
1 stop26h 28m
Deal found 8/2![Copa Airlines logo]()
$410
This Copa Airlines deal was found by Cheapflights users on 8/7. 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 9/1310:03 am -
1 stop13h 59m
Sat 9/193:20 pm -
1 stop18h 44m
Deal found 8/7![Copa Airlines logo]()
$413
This Copa Airlines deal was found by Cheapflights users on 8/3. 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 10/95:55 pm -
1 stop19h 04m
Fri 10/168:01 am -
1 stop24h 23m
Deal found 8/3![Copa Airlines logo]()
$414
This Copa Airlines deal was found by Cheapflights users on 8/5. 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 10/155:55 pm -
1 stop19h 04m
Tue 10/208:01 am -
1 stop24h 09m
Deal found 8/5![Copa Airlines logo]()
$416
This Copa Airlines deal was found by Cheapflights users on 8/2. 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 10/54:08 am -
1 stop8h 51m
Wed 10/148:01 am -
1 stop24h 09m
Deal found 8/2![Copa Airlines logo]()
$423
This Copa Airlines deal was found by Cheapflights users on 8/2. 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 9/194:08 am -
1 stop8h 51m
Tue 9/228:01 am -
1 stop11h 58m
Deal found 8/2![Copa Airlines logo]()
$426
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 7, 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 7, 2026.
This Copa Airlines deal was found by Cheapflights users on 8/5. 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 10/263:58 am -
1 stop20h 07m
Fri 11/62:13 pm -
1 stop20h 46m
Deal found 8/5![Copa Airlines logo]()
$398
This Copa Airlines deal was found by Cheapflights users on 8/2. 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 10/95:55 pm -
1 stop19h 04m
Sat 10/173:20 pm -
1 stop17h 59m
Deal found 8/2![Copa Airlines logo]()
$408
This Copa Airlines deal was found by Cheapflights users on 8/4. 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 11/28:44 am -
1 stop15h 27m
Sat 11/72:13 pm -
1 stop16h 49m
Deal found 8/4![Copa Airlines logo]()
$413
This Copa Airlines deal was found by Cheapflights users on 8/5. 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 10/1610:03 am -
1 stop13h 54m
Sat 10/248:01 am -
1 stop24h 03m
Deal found 8/5![Copa Airlines logo]()
$413
This Copa Airlines deal was found by Cheapflights users on 8/7. 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 9/1310:03 am -
1 stop13h 59m
Sat 9/193:20 pm -
1 stop18h 44m
Deal found 8/7![Copa Airlines logo]()
$413
This Copa Airlines deal was found by Cheapflights users on 8/2. 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 10/54:08 am -
1 stop8h 51m
Wed 10/148:01 am -
1 stop24h 09m
Deal found 8/2![Copa Airlines logo]()
$423
This Copa Airlines deal was found by Cheapflights users on 8/2. 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 9/194:08 am -
1 stop8h 51m
Tue 9/228:01 am -
1 stop11h 58m
Deal found 8/2![Copa Airlines logo]()
$426
This Copa Airlines deal was found by Cheapflights users on 8/2. 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 10/2410:03 am -
1 stop13h 54m
Sat 11/72:13 pm -
1 stop16h 49m
Deal found 8/2![Copa Airlines logo]()
$441
This Copa Airlines deal was found by Cheapflights users on 8/7. 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 9/125:55 pm -
1 stop19h 04m
Sun 9/203:20 pm -
1 stop16h 50m
Deal found 8/7![Copa Airlines logo]()
$445
This Copa Airlines deal was found by Cheapflights users on 8/2. 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 8/2510:03 am -
1 stop13h 59m
Sun 8/308:02 am -
1 stop24h 08m
Deal found 8/2![Copa Airlines logo]()
$506
This Copa Airlines deal was found by Cheapflights users on 8/3. 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 8/294:08 am -
1 stop19h 54m
Sat 9/53:20 pm -
1 stop18h 44m
Deal found 8/3![Copa Airlines logo]()
$506
This Copa Airlines deal was found by Cheapflights users on 8/7. 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 8/2910:03 am -
1 stop13h 59m
Wed 9/28:01 am -
1 stop26h 03m
Deal found 8/7![Copa Airlines logo]()
$527
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 7, 2026 and is based on user searches.
Discover last-minute flight deals from San José to O'Hare Intl. Data last updated August 7, 2026 and is based on user searches.
This Volaris deal was found by Cheapflights users on 8/3. 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 8/254:15 pm -
1 stop18h 54m
Sun 8/306:21 am -
1 stop18h 38m
Deal found 8/3![Multiple Airlines logo]()
$440
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/44:08 am -
1 stop8h 51m
Wed 9/93:20 pm -
1 stop7h 28m
Deal found 8/3![Copa Airlines logo]()
$464
This Copa Airlines deal was found by Cheapflights users on 8/7. 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 9/125:55 pm -
1 stop19h 04m
Sun 9/203:20 pm -
1 stop16h 50m
Deal found 8/7![Copa Airlines logo]()
$445
This Copa Airlines deal was found by Cheapflights users on 8/5. 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 9/125:55 pm -
1 stop19h 04m
Sat 9/198:01 am -
1 stop26h 03m
Deal found 8/5![Copa Airlines logo]()
$463
This Copa Airlines deal was found by Cheapflights users on 8/7. 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 9/1310:03 am -
1 stop13h 59m
Sat 9/193:20 pm -
1 stop18h 44m
Deal found 8/7![Copa Airlines logo]()
$413
This Copa Airlines deal was found by Cheapflights users on 8/3. 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 -
1 stop13h 59m
Sat 9/193:20 pm -
1 stop16h 50m
Deal found 8/3![Copa Airlines logo]()
$392
This Copa Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:03 am -
1 stop26h 56m
Tue 9/228:01 am -
1 stop24h 09m
Deal found 8/5![Copa Airlines logo]()
$379
This Copa Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:03 am -
1 stop13h 59m
Thu 10/18:01 am -
1 stop26h 03m
Deal found 8/4![Copa Airlines logo]()
$381
This Copa Airlines deal was found by Cheapflights users on 8/2. 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 9/194:08 am -
1 stop8h 51m
Tue 9/228:01 am -
1 stop11h 58m
Deal found 8/2![Copa Airlines logo]()
$426
This deal was found by Cheapflights users on 8/7. 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.
Mon 9/217:55 am -
1 stop11h 10m
Thu 9/248:45 am -
1 stop11h 52m
Deal found 8/7![United Airlines logo]()
$407
This Copa Airlines deal was found by Cheapflights users on 8/4. 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 9/2510:03 am -
1 stop26h 56m
Thu 10/18:01 am -
1 stop24h 09m
Deal found 8/4![Copa Airlines logo]()
$397
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 7, 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 7, 2026.
This Viva deal was found by Cheapflights users on 8/6. 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 9/241:15 pm -
1 stop24h 37m
Deal found 8/6![Viva logo]()
$164
This Viva deal was found by Cheapflights users on 8/2. 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 10/221:15 pm -
1 stop22h 55m
Deal found 8/2![Viva logo]()
$203
This Super.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:05 pm -
1 stop9h 03m
Deal found 8/5![JetBlue logo]()
$220
This Volaris deal was found by Cheapflights users on 8/7. 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 -
1 stop18h 54m
Deal found 8/7![Multiple Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 10/38:55 am -
2 stops25h 45m
Deal found 8/4![Multiple Airlines logo]()
$258
This Volaris deal was found by Cheapflights users on 8/6. 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 9/134:15 pm -
1 stop18h 54m
Deal found 8/6![Multiple Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Sun 9/277:00 am -
1 stop27h 00m
Deal found 8/5![Multiple Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:00 am -
1 stop27h 00m
Deal found 8/3![Multiple Airlines logo]()
$269
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 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $379 (Copa Airlines) |
One-way from | $164 (Viva) |
Popular in | July |
Cheapest in | February |
Average price | $503 |
Good round-trip deal | $491 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 2,558,603 searches. Data last updated August 7, 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
Mon 10/26
3:58 am-1:05 am
1 stop20h 07m
Chicago O'Hare Intl
Fri 11/6
2:13 pm-10:59 am
1 stop20h 46m
$398
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Fri 10/9
5:55 pm-1:59 pm
1 stop19h 04m
Chicago O'Hare Intl
Sat 10/17
3:20 pm-8:19 am
1 stop17h 59m
$408
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Mon 11/2
8:44 am-12:11 am
1 stop15h 27m
Chicago O'Hare Intl
Sat 11/7
2:13 pm-7:02 am
1 stop16h 49m
$413
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Fri 10/16
10:03 am-12:57 am
1 stop13h 54m
Chicago O'Hare Intl
Sat 10/24
8:01 am-7:04 am
1 stop24h 03m
$413
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sun 9/13
10:03 am-1:02 am
1 stop13h 59m
Chicago O'Hare Intl
Sat 9/19
3:20 pm-9:04 am
1 stop18h 44m
$413
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Mon 10/5
4:08 am-1:59 pm
1 stop8h 51m
Chicago O'Hare Intl
Wed 10/14
8:01 am-7:10 am
1 stop24h 09m
$423
Quickest round-trip
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sat 9/19
4:08 am-1:59 pm
1 stop8h 51m
Chicago O'Hare Intl
Tue 9/22
8:01 am-6:59 pm
1 stop11h 58m
$426
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sat 10/24
10:03 am-12:57 am
1 stop13h 54m
Chicago O'Hare Intl
Sat 11/7
2:13 pm-7:02 am
1 stop16h 49m
$441
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Sat 9/12
5:55 pm-1:59 pm
1 stop19h 04m
Chicago O'Hare Intl
Sun 9/20
3:20 pm-7:10 am
1 stop16h 50m
$445
San JoséChicago
SJO San José Juan Santamaria Intl - ORD Chicago O'Hare Intl
SJOORD
San José Juan Santamaria Intl
Tue 8/25
10:03 am-1:02 am
1 stop13h 59m
Chicago O'Hare Intl
Sun 8/30
8:02 am-7:10 am
1 stop24h 08m
$506
Showing 1-10 of 21 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 $389). 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.
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 August 7, 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 6% of weekly flights between San José and Chicago have experienced delays in the past year, with the average delay time being 252 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 7, 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
7.4
Entertainment
6.8
Food
6.9
Overall
7.6
Boarding
7.8
Crew
8.1
Reviews
1 / 20
4.0
OkayPaul,Jun 2025
PTY - MIA
Comfort
7.4
Entertainment
6.8
Food
6.9
Overall
7.6
Boarding
7.8
Crew
8.1
Reviews
1 / 20
4.0
OkayPaul,Jun 2025
PTY - MIA
Comfort
7.4
Entertainment
6.8
Food
6.9
Overall
7.6
Boarding
7.8
Crew
8.1
Reviews
1 / 20
4.0
OkayPaul,Jun 2025
PTY - MIA
Comfort
7.4
Entertainment
6.8
Food
6.9
Overall
7.6
Boarding
7.8
Crew
8.1
Reviews
1 / 20
4.0
OkayPaul,Jun 2025
PTY - MIA
Comfort
7.4
Entertainment
6.8
Food
6.9
Overall
7.6
Boarding
7.8
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
Gurnee
South Holland
Libertyville
Orland Park
Hoffman Estates
Beloit
Rockford
Aurora
Racine
Great Lakes
Janesville
Joliet
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Other flights to O'Hare Intl
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San José and O'Hare Intl flights
Browse other San José and O'Hare Intl flight options. Last updated on August 7, 2026.
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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 August 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$189 | Average$493 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$332 | Average$518 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$370 | Average$491 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$375 | Average$636 | FlexibilityNo cancel fee | On-time71% |