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San José

$74+ Cheap flights from O'Hare Intl (ORD) to San José (SJO)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJO
Nov 1 — Nov 81
Sat 11/1
Sat 11/8
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to San José Juan Santamaria Intl are usually found in October or September, booked 53 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from O'Hare Intl to San José

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to San José (SJO). 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 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(Priceline)

One-way from

$74
(Cheapflightsfares)

Popular in

December

Cheapest in

October

Average price

$387

Good round-trip deal

$525 or less

Good one-way deal

$150 or less
Provider with most accurate pricing for Chicago O'Hare Intl-San José Juan Santamaria Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-San José Juan Santamaria Intl flights.
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From Chicago O'Hare Intl to San José Juan Santamaria Intl
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One-way flight from Chicago O'Hare Intl to San José Juan Santamaria Intl
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Highest demand for flights based on searches. 10% potential increase in price ($70 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to San José Juan Santamaria Intl.
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Price to beat on a one-way flight from Chicago O'Hare Intl to San José Juan Santamaria Intl.
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Find flight deals from O'Hare Intl to San José

Cheapest flights from O'Hare Intl to San José
Explore the most affordable flight options available from O'Hare Intl to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 2, 2025.

This Priceline deal was found by Cheapflights users on 10/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:58 pmORD - SJO
2 stops17h 32mSpirit Airlines
Tue 10/2812:35 pmSJO - ORD
1 stop11h 28mSpirit Airlines
Deal found 10/1$249
This Mytrip deal was found by Cheapflights users on 10/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/88:28 amORD - SJO
2 stops27h 11mSpirit Airlines
Tue 11/111:30 pmSJO - ORD
1 stop10h 57mSpirit Airlines
Deal found 10/2$251
This Spirit deal was found by Cheapflights users on 10/1. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/187:43 pmORD - SJO
1 stop16h 47mSpirit Airlines
Thu 11/61:30 pmSJO - ORD
1 stop10h 57mSpirit Airlines
Deal found 10/1$252
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 10/187:43 pmORD - SJO
1 stop16h 47mSpirit Airlines
Tue 10/2812:35 pmSJO - ORD
1 stop11h 28mSpirit Airlines
Deal found 10/1$253
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/157:43 pmORD - SJO
2 stops15h 58mSpirit Airlines
Wed 11/51:30 pmSJO - ORD
1 stop10h 57mSpirit Airlines
Deal found 10/1$254
This Spirit deal was found by Cheapflights users on 10/1. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/157:43 pmORD - SJO
1 stop16h 47mSpirit Airlines
Sat 10/2512:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Deal found 10/1$255
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 10/177:43 pmORD - SJO
1 stop16h 47mSpirit Airlines
Sat 10/2512:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Deal found 10/1$256
This Cheapflightsfares deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/68:41 amORD - SJO
1 stop15h 40mSpirit Airlines
Tue 12/91:16 amSJO - ORD
1 stop8h 07mSpirit Airlines
Deal found 10/1$257
This CheapOair deal was found by Cheapflights users on 9/30. 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 10/116:58 pmORD - SJO
2 stops17h 32mSpirit Airlines
Tue 10/1412:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Deal found 9/30$258
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/225:05 amORD - SJO
2 stops30h 36mSpirit Airlines
Sat 10/2511:37 amSJO - ORD
1 stop8h 56mSpirit Airlines
Deal found 9/30$259
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 10/177:43 pmORD - SJO
1 stop16h 47mSpirit Airlines
Fri 10/2412:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Deal found 10/1$261

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to San José 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 October 2, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to San José that are best for you.

Fly from

O'Hare Intl

Fly to

San José

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 11/29

7:39 am-12:56 pm

Nonstop5h 17m

San José Juan Santamaria Intl

Sat 12/6

2:05 pm-7:35 pm

Nonstop5h 30m

$325

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 11/3

2:07 pm-7:33 am

1 stop17h 26m

San José Juan Santamaria Intl

Mon 11/10

11:00 am-12:05 am

1 stop13h 05m

$328

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 1/19

2:13 pm-7:06 am

1 stop16h 53m

San José Juan Santamaria Intl

Tue 1/27

4:09 am-12:46 pm

1 stop8h 37m

$328

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 2/16

2:22 pm-8:21 am

1 stop17h 59m

San José Juan Santamaria Intl

Tue 2/24

4:09 am-12:31 pm

1 stop8h 22m

$328

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 10/30

7:59 am-6:58 pm

1 stop11h 59m

San José Juan Santamaria Intl

Mon 11/3

4:08 am-12:46 pm

1 stop8h 38m

$328

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 2/12

2:22 pm-7:06 am

1 stop16h 44m

San José Juan Santamaria Intl

Mon 2/16

5:51 pm-12:31 pm

1 stop18h 40m

$328

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 11/7

2:07 pm-7:33 am

1 stop17h 26m

San José Juan Santamaria Intl

Mon 11/10

4:08 am-12:46 pm

1 stop8h 38m

$328

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 2/11

2:22 pm-7:06 am

1 stop16h 44m

San José Juan Santamaria Intl

Tue 2/17

5:51 pm-12:31 pm

1 stop18h 40m

$328

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 11/1

3:07 pm-8:19 am

1 stop18h 12m

San José Juan Santamaria Intl

Thu 11/6

2:53 pm-12:05 am

1 stop9h 12m

$328

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 11/18

2:07 pm-8:19 am

1 stop18h 12m

San José Juan Santamaria Intl

Mon 11/24

11:00 am-12:05 am

1 stop13h 05m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/2

Showing 1-10 of 20 results
1
2

Compare providers for flights from O'Hare Intl to San José

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 O'Hare Intl to San José in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
CheapfaremartPrice Accuracy-Trust Score*1 star

*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 Chicago O'Hare Intl Airport-San José, San José Province flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-San José, San José Province flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-San José, San José Province flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-San José, San José Province 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 Chicago O'Hare Intl Airport-San José, San José Province 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 O'Hare Intl to San José

Have a flexible travel schedule? Discover the best time to fly to San José from O'Hare Intl 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 Chicago O'Hare Intl Airport to San José

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

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to San José. Price data was last updated on September 26, 2025.

The best time to book flights from Chicago O'Hare Intl Airport to San José, San José Province is 53 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to San José, San José Province (average of $392). Flying from Chicago O'Hare Intl Airport to San José, San José Province in March is currently the most expensive (average of $552). 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 ORD to SJO?

Find hourly flight availability from O'Hare Intl to San José. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 2, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 43% on flights from Chicago O'Hare Intl Airport to San José, San José Province by exploring options for tickets in the evening.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to San José, San José Province?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to San José. Price data was last updated on September 28, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to San José, San José Province flight should consider departing on Tuesday evenings when fares are most often at their lowest. Wednesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing San José

Get insights into the airlines that provide service to San José. 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 San José. Reviews last updated October 2, 2025.
See what other customers who have flown with Copa Airlines, United Airlines, and American Airlines from Chicago O'Hare Intl Airport to San José have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.6
Good
1,542 reviews

Food

6.8

Overall

7.6

Boarding

7.8

Entertainment

6.8

Comfort

7.4

Crew

8.1

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
1,542 reviews
Copa Airlines
7.6
Good
1,542 reviews

Food

6.8

Overall

7.6

Boarding

7.8

Entertainment

6.8

Comfort

7.4

Crew

8.1

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
8,933 reviews
Copa Airlines
7.6
Good
1,542 reviews

Food

6.8

Overall

7.6

Boarding

7.8

Entertainment

6.8

Comfort

7.4

Crew

8.1

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
11,033 reviews
Copa Airlines
7.6
Good
1,542 reviews

Food

6.8

Overall

7.6

Boarding

7.8

Entertainment

6.8

Comfort

7.4

Crew

8.1

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
6.7
Okay
2,443 reviews
Copa Airlines
7.6
Good
1,542 reviews

Food

6.8

Overall

7.6

Boarding

7.8

Entertainment

6.8

Comfort

7.4

Crew

8.1

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
8,070 reviews
Copa Airlines
7.6
Good
1,542 reviews

Food

6.8

Overall

7.6

Boarding

7.8

Entertainment

6.8

Comfort

7.4

Crew

8.1

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 O'Hare Intl to San José. 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 into for flights to San José from Chicago O'Hare Intl?

    Located just 8.8 mi from the city center, San José Juan Santamaria Intl is the airport most travelers will use when flying to San José from Chicago O'Hare Intl. Booking flights from Chicago O'Hare Intl to Juan Santamaria Intl (SJO) should be relatively easy as there are 0 daily inbound flights from Chicago O'Hare Intl from 9 different airlines.

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

    There are many flights that can get you from Chicago O'Hare Intl Airport to San José, San José Province in 5h 17m. Fly via United Airlines or Copa Airlines to get the fastest option. There are 2220 mi between Chicago O'Hare Intl Airport and San José, San José Province. This flight may include one or multiple stops.

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

    Flying on Spirit Airlines is currently your cheapest option to San José, San José Province, with prices starting at $263. Additional round-trip tickets that might be worth considering are offered by Delta and Avianca, with the lowest prices starting at $290 and $307, respectively. These flights start at 53% lower than the current average price 3 months from now.

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

    Looking at all options, your cheapest flight can be booked for $150. While the most popular route (Chicago O'Hare Intl - San José Juan Santamaria Intl) can be booked for $180 on average, our data indicates $685 when flying from Chicago O'Hare Intl Airport to San José, San José Province.

  • Where are the most common layover locations when flying from Chicago O'Hare Intl Airport to San José, San José Province?

    Most of the time, Chicago O'Hare Intl Airport to San José, San José Province flights that have layovers will stop in Fort Lauderdale.

  • What are some popular things to do or see while on a layover in Fort Lauderdale?

    The majority of Fort Lauderdale visitors spend their time at Las Olas Beach, Port Everglades, and Fort Lauderdale Beach Park. Las Olas Beach, Port Everglades, and Fort Lauderdale Beach Park can be visited by traveling about 4.1 mi, 2.1 mi, and 4.2 mi respectively from Fort Lauderdale. Those on a layover in Fort Lauderdale in need of a rental car can book one at Fort Lauderdale for about $20.

  • Where are the least popular layover locations for Chicago O'Hare Intl Airport to San José, San José Province flights?

    Chicago O'Hare Intl Airport to San José, San José Province flights have a layover in Panama City the least frequently.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from O'Hare Intl to San José 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 Chicago O'Hare Intl Airport to San José, San José Province?

    Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to San José, San José Province (average of $392). Flying from Chicago O'Hare Intl Airport to San José, San José Province in March is currently the most expensive (average of $552). 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 San José?

Book flights to San José if you plan to visit one of these locations
Heredia
Manuel Antonio
Alajuela
Monteverde
Jacó

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Alternative routes for O'Hare Intl to San José

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

Top 9 airlines flying from O'Hare Intl to San José

Discover the top 9 airlines that operate flights from O'Hare Intl to San José. 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 October 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$263Average$436FlexibilityNo cancel feeOn-time65%
DeltaCheapest$290Average$674FlexibilityNo cancel feeOn-timeN/A
AviancaCheapest$307Average$463FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$314Average$533FlexibilityNo cancel feeOn-time70%
FrontierCheapest$345Average$796FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$432Average$635FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$441Average$613FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$442Average$651FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$464Average$724FlexibilityNo cancel feeOn-time69%

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