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O'Hare Intl

$120+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — ORD
Dec 24 — Dec 311
Wed 12/24
Wed 12/31
1 adult, Economy
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Cheapflights Tip: The best prices from San José Juan Santamaria Intl to Chicago O'Hare Intl are usually found in September or February, booked 90 days in advance, depart on a Friday or Thursday and return on a Tuesday

Cheap 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 November 24, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$267
(Mytrip)

One-way from

$120
(Cheapflightsfares)

Popular in

April

Cheapest in

September

Average price

$449

Good round-trip deal

$325 or less

Good one-way deal

$175 or less
Provider with most accurate pricing for San José Juan Santamaria Intl-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-Chicago O'Hare Intl flights.
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From San José Juan Santamaria Intl to Chicago O'Hare Intl
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One-way flight from San José Juan Santamaria Intl to Chicago O'Hare Intl
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Highest demand for flights based on searches. 3% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from San José Juan Santamaria Intl to Chicago O'Hare Intl.
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Price to beat on a one-way flight from San José Juan Santamaria Intl to Chicago O'Hare Intl.
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Find flight deals from San José to O'Hare Intl

Cheapest flights from San José to O'Hare Intl
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 November 24, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/241:31 pmSJO - ORD
1 stop25h 31mMultiple Airlines
Wed 12/313:26 pmORD - SJO
1 stop20h 59mMultiple Airlines
Deal found 11/24$268
This Kiwi.com deal was found by Cheapflights users on 11/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/242:52 pmSJO - ORD
1 stop31h 32mMultiple Airlines
Mon 1/128:22 pmORD - SJO
2 stops15h 15mMultiple Airlines
Deal found 11/22$270
This CheapOair deal was found by Cheapflights users on 11/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2012:39 pmSJO - ORD
2 stops11h 51mSpirit Airlines
Sun 1/118:22 pmORD - SJO
2 stops15h 15mSpirit Airlines
Deal found 11/22$273
This CheapOair deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/912:39 pmSJO - ORD
2 stops11h 30mSpirit Airlines
Thu 1/88:22 pmORD - SJO
1 stop16h 00mSpirit Airlines
Deal found 11/24$274
This Kiwi.com deal was found by Cheapflights users on 11/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/211:31 pmSJO - ORD
1 stop10h 59mSpirit Airlines
Mon 1/125:15 amORD - SJO
1 stop7h 07mSpirit Airlines
Deal found 11/22$275
This CheapOair deal was found by Cheapflights users on 11/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2012:39 pmSJO - ORD
2 stops11h 51mSpirit Airlines
Tue 1/205:15 amORD - SJO
1 stop7h 07mSpirit Airlines
Deal found 11/22$276
This KAYAK deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/241:31 pmSJO - ORD
1 stop10h 59mSpirit Airlines
Wed 12/313:26 pmORD - SJO
2 stops20h 16mSpirit Airlines
Deal found 11/24$277
This OneTravel deal was found by Cheapflights users on 11/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/291:31 pmSJO - ORD
1 stop21h 43mSpirit Airlines
Tue 1/275:15 amORD - SJO
1 stop7h 07mSpirit Airlines
Deal found 11/22$281

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 November 24, 2025.
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

San José

Fly to

O'Hare Intl

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 12/5

4:08 am-12:52 pm

1 stop8h 44m

Chicago O'Hare Intl

Wed 12/10

2:07 pm-8:19 am

1 stop18h 12m

$358

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 12/20

6:07 pm-12:52 pm

1 stop18h 45m

Chicago O'Hare Intl

Sun 1/25

2:13 pm-4:46 pm

3 stops26h 33m

$363

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 12/9

4:08 am-12:52 pm

1 stop8h 44m

Chicago O'Hare Intl

Fri 12/12

2:07 pm-7:10 am

1 stop17h 03m

$378

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 12/25

2:05 pm-7:35 pm

Nonstop5h 30m

Chicago O'Hare Intl

Mon 1/5

7:39 am-12:56 pm

Nonstop5h 17m

$395

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 2/13

2:05 pm-7:35 pm

Nonstop5h 30m

Chicago O'Hare Intl

Mon 2/16

7:39 am-12:56 pm

Nonstop5h 17m

$395

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 12/24

2:05 pm-7:35 pm

Nonstop5h 30m

Chicago O'Hare Intl

Mon 1/12

7:39 am-12:56 pm

Nonstop5h 17m

$395

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sun 3/8

6:08 pm-1:31 pm

1 stop18h 23m

Chicago O'Hare Intl

Mon 3/16

3:22 pm-7:05 am

1 stop16h 43m

$397

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 3/12

11:01 am-1:04 am

1 stop13h 03m

Chicago O'Hare Intl

Mon 3/16

3:22 pm-7:05 am

1 stop16h 43m

$397

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 2/26

5:50 am-12:04 am

1 stop18h 14m

Chicago O'Hare Intl

Thu 3/12

3:22 pm-7:05 am

1 stop16h 43m

$397

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 5/1

5:50 am-1:24 am

1 stop18h 34m

Chicago O'Hare Intl

Sun 5/10

3:13 pm-7:06 am

1 stop16h 53m

$397

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/23

Showing 1-10 of 21 results
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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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on San José-Chicago O'Hare Intl Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on San José-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.
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

How far ahead should I book a flight from San José to Chicago O'Hare Intl Airport?

Use this chart to determine the optimal time to book a round-trip flight from San José to O'Hare Intl. Price data was last updated on November 21, 2025.

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 61 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, October is the cheapest month in which you can book a flight from San José to Chicago O'Hare Intl Airport (average of $195). Flying from San José to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $353). 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 November 24, 2025.

One of the essential ways to save on airfare from San José to Chicago O'Hare Intl Airport is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 31% on airfare.

How much does it cost to fly round-trip from San José to Chicago O'Hare Intl Airport?

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 November 24, 2025.
See what other customers who have flown with Copa Airlines, United Airlines, and American 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.
Copa Airlines
7.6
Good
1,567 reviews

Food

6.8

Entertainment

6.8

Overall

7.6

Comfort

7.4

Crew

8.1

Boarding

7.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
Copa Airlines
7.6
Good
1,567 reviews
Copa Airlines
7.6
Good
1,567 reviews

Food

6.8

Entertainment

6.8

Overall

7.6

Comfort

7.4

Crew

8.1

Boarding

7.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
United Airlines
7.4
Good
9,039 reviews
Copa Airlines
7.6
Good
1,567 reviews

Food

6.8

Entertainment

6.8

Overall

7.6

Comfort

7.4

Crew

8.1

Boarding

7.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
American Airlines
7.2
Good
11,043 reviews
Copa Airlines
7.6
Good
1,567 reviews

Food

6.8

Entertainment

6.8

Overall

7.6

Comfort

7.4

Crew

8.1

Boarding

7.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
Avianca
6.6
Okay
2,478 reviews
Copa Airlines
7.6
Good
1,567 reviews

Food

6.8

Entertainment

6.8

Overall

7.6

Comfort

7.4

Crew

8.1

Boarding

7.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
Spirit Airlines
6.3
Okay
8,159 reviews
Copa Airlines
7.6
Good
1,567 reviews

Food

6.8

Entertainment

6.8

Overall

7.6

Comfort

7.4

Crew

8.1

Boarding

7.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip

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.

  • What airport do you fly from for flights from San José to Chicago O'Hare Intl?

    San José Juan Santamaria Intl (SJO) is the airport you will fly out of if you book a flight from San José to Chicago O'Hare Intl. You should not have trouble finding flights to Chicago O'Hare Intl from Juan Santamaria Intl; the airport handles an average of 1 outbound flight to Chicago O'Hare Intl per day. You should also have plenty of airline options to choose from since 6 airlines have flights from the San José airport to Chicago O'Hare Intl. It is only a 8.8 mi journey to Juan Santamaria Intl (SJO) from San José’s city center.

  • How long is the flight from San José to Chicago O'Hare Intl Airport?

    Airlines like Copa Airlines and United Airlines fly from San José to Chicago O'Hare Intl Airport in about 5h 30m. The time it takes to get you to your destination can typically vary by up to 3h 14m. San José and Chicago O'Hare Intl Airport are separated by a distance of 2220 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from San José to Chicago O'Hare Intl Airport round-trip?

    Our cheapest airline available from San José to Chicago O'Hare Intl Airport is Spirit Airlines. Our recent data shows that you can find tickets from as low as $230 on this airline. Additional options worth looking into are Avianca and Copa Airlines, starting at $249 and $314 round-trip. Spirit Airlines is currently priced 50% below the average price you’ll pay for this route.

  • What are the cheapest flights from San José to Chicago O'Hare Intl Airport?

    The cheapest flight price from San José to Chicago O'Hare Intl Airport is $145. On average you can expect to pay $351. The most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl), can usually be booked for $248.

  • Can I find deals for flights from San José to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on San José to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San José to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San José to O'Hare Intl.

  • Can I find deals for business class flights from San José to O'Hare Intl?

    Yes. Cheapflights offers flight deals from San José to O'Hare Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San José to Chicago O'Hare Intl Airport?

    Currently, October is the cheapest month in which you can book a flight from San José to Chicago O'Hare Intl Airport (average of $195). Flying from San José to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $353). 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.

See more FAQs

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 locations
Schaumburg
Rosemont
Skokie
Des Plaines
Gurnee
Hoffman Estates
Beloit
Delavan
Elgin
Oak Brook
Elk Grove Village
Downers Grove
Rockford
Naperville
Orland Park
Bridgeview
Warrenville
Waukegan
Aurora
Racine

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for San José to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
San José to Midway flights
Liberia to O'Hare Intl flights

Top 6 airlines flying from San José to O'Hare Intl

Discover the top 6 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 November 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$230Average$398FlexibilityNo cancel feeOn-time65%
AviancaCheapest$249Average$485FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$314Average$458FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$324Average$463FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$425Average$527FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$434Average$573FlexibilityNo cancel feeOn-time69%

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