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San José

$137+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJO
Aug 2 — Aug 91
Sun 8/2
Sun 8/9
1 adult, Economy
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1. Tell us where you want to go

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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 44 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

Cheap 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 July 3, 2026.

This Booking.com deal was found by Cheapflights users on 7/2. 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.
Sun 8/163:21 pm
ORD
-
SJO
1 stop17h 58m
Copa Airlines
Sun 8/234:08 am
SJO
-
ORD
1 stop19h 54m
Copa Airlines
Deal found 7/2$489
This Copa Airlines deal was found by Cheapflights users on 7/1. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:13 pm
ORD
-
SJO
1 stop26h 36m
Copa Airlines
Wed 11/112:45 pm
SJO
-
ORD
1 stop9h 26m
Copa Airlines
Deal found 7/1$490
This Viva deal was found by Cheapflights users on 7/1. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/311:30 am
ORD
-
SJO
1 stop24h 50m
Viva
Fri 8/72:20 am
SJO
-
ORD
1 stop21h 20m
Viva
Deal found 7/1$492
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Tue 10/205:22 am
ORD
-
SJO
2 stops8h 38m
American Airlines
Wed 10/281:05 pm
SJO
-
ORD
1 stop8h 26m
American Airlines
Deal found 6/28$495
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:44 pm
ORD
-
SJO
1 stop20h 27m
Multiple Airlines
Wed 9/307:07 am
SJO
-
ORD
2 stops13h 27m
Multiple Airlines
Deal found 6/28$496
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:13 pm
ORD
-
SJO
1 stop16h 07m
Frontier
Sat 8/89:45 am
SJO
-
ORD
1 stop12h 25m
Frontier
Deal found 6/30$498
This CheapOair deal was found by Cheapflights users on 7/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:13 pm
ORD
-
SJO
1 stop16h 07m
Frontier
Sun 7/269:35 am
SJO
-
ORD
1 stop22h 36m
Frontier
Deal found 7/2$499
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Tue 12/86:45 am
ORD
-
SJO
1 stop7h 17m
American Airlines
Tue 12/2211:32 am
SJO
-
ORD
1 stop13h 06m
American Airlines
Deal found 6/28$502
This Volaris deal was found by Cheapflights users on 6/29. 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 9/31:49 pm
ORD
-
SJO
1 stop11h 10m
Multiple Airlines
Sun 9/64:15 pm
SJO
-
ORD
1 stop18h 54m
Multiple Airlines
Deal found 6/29$503
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Sun 9/64:22 pm
ORD
-
SJO
1 stop20h 53m
Multiple Airlines
Tue 9/227:07 am
SJO
-
ORD
2 stops13h 27m
Multiple Airlines
Deal found 6/30$504
This Copa Airlines deal was found by Cheapflights users on 6/29. 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 7/273:21 pm
ORD
-
SJO
1 stop20h 45m
Copa Airlines
Sat 8/14:08 am
SJO
-
ORD
1 stop8h 51m
Copa Airlines
Deal found 6/29$505
This American Airlines deal was found by Cheapflights users on 6/28. 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 8/278:19 am
ORD
-
SJO
2 stops12h 34m
American Airlines
Tue 9/11:03 pm
SJO
-
ORD
1 stop10h 15m
American Airlines
Deal found 6/28$507

Find 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 July 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$489
(Booking.com)

One-way from

$137
(Cheapflightsfares)

Popular in

December

Cheapest in

October

Average price

$606

Good round-trip deal

$652 or less
Provider with most accurate pricing for Chicago O'Hare Intl-San José Juan Santamaria Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago O'Hare Intl-San José Juan Santamaria Intl flights.
Search Deals
From Chicago O'Hare Intl to San José Juan Santamaria Intl
Search Deals
One-way flight from Chicago O'Hare Intl to San José Juan Santamaria Intl
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to San José Juan Santamaria Intl.
Search Deals

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 July 3, 2026.
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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 11/4

2:13 pm-4:49 pm

1 stop26h 36m

San José Juan Santamaria Intl

Wed 11/11

2:45 pm-12:11 am

1 stop9h 26m

$490

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 8/19

8:02 am-7:10 am

1 stop24h 08m

San José Juan Santamaria Intl

Mon 8/31

4:08 am-1:02 am

1 stop19h 54m

$490

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 10/28

8:35 am-8:19 am

1 stop24h 44m

San José Juan Santamaria Intl

Wed 11/4

3:59 am-12:46 pm

1 stop8h 47m

$490
Quickest round-trip

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 11/28

7:17 am-12:35 pm

Nonstop5h 18m

San José Juan Santamaria Intl

Tue 12/8

2:00 pm-11:42 pm

1 stop9h 42m

$498

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 7/27

3:21 pm-11:06 am

1 stop20h 45m

San José Juan Santamaria Intl

Sat 8/1

4:08 am-1:59 pm

1 stop8h 51m

$505

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 8/15

8:02 am-7:10 am

1 stop24h 08m

San José Juan Santamaria Intl

Sat 8/22

10:03 am-1:02 am

1 stop13h 59m

$525

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 7/26

3:21 pm-8:21 am

1 stop18h 00m

San José Juan Santamaria Intl

Tue 8/4

4:08 am-1:02 am

1 stop19h 54m

$566

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 7/21

3:21 pm-7:12 am

1 stop16h 51m

San José Juan Santamaria Intl

Fri 7/31

6:17 pm-1:59 pm

1 stop18h 42m

$581

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 7/30

3:21 pm-7:12 am

1 stop16h 51m

San José Juan Santamaria Intl

Fri 8/14

4:08 am-1:59 pm

1 stop8h 51m

$590

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 7/15

3:21 pm-8:21 am

1 stop18h 00m

San José Juan Santamaria Intl

Fri 7/17

5:45 am-12:01 am

1 stop17h 16m

$596

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 24 resultsSorted by cheapest first
1
2
3

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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice 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 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 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 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 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 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?

To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to San José, you should look to book at least 43 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, October is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to San José (average of $361). Flying from Chicago O'Hare Intl Airport to San José in December is currently the most expensive (average of $672). 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 July 3, 2026.

When flying from Chicago O'Hare Intl Airport to San José, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

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 July 3, 2026.
See what other customers who have flown with Southwest,Copa Airlines, andUnited 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.
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Entertainment

7.5

Overall

7.9

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Entertainment

7.5

Overall

7.9

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Copa Airlines
7.6
Good
1,567 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Entertainment

7.5

Overall

7.9

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
United Airlines
7.4
Good
9,927 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Entertainment

7.5

Overall

7.9

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
American Airlines
7.1
Good
11,766 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Entertainment

7.5

Overall

7.9

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Avianca
6.5
Okay
2,517 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Entertainment

7.5

Overall

7.9

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.

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 10 different airlines.

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

    A quick flight from Chicago O'Hare Intl Airport to San José can take about 5h 18m. Copa Airlines provides one of the quickest options available for as low as $498. The distance between Chicago O'Hare Intl Airport and San José is about 2220 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Flying on Avianca is currently your cheapest option to San José, with prices starting at $148. Additional round-trip tickets that might be worth considering are offered by Delta and Frontier, with the lowest prices starting at $221 and $271, respectively. Avianca is priced at 72% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to San José one-way?

    The cheapest airlines for a one-way flight from Chicago O'Hare Intl Airport to San José are Frontier ($135), Delta ($136), and American Airlines ($150).

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

    Looking at all options, your cheapest flight can be booked for $497. While the most popular route (Chicago O'Hare Intl - San José Juan Santamaria Intl) can be booked for $394 on average, our data indicates $789 when flying from Chicago O'Hare Intl Airport to San José.

  • 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?

    Currently, October is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to San José (average of $361). Flying from Chicago O'Hare Intl Airport to San José in December is currently the most expensive (average of $672). 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
Alajuela
Jacó
Heredia
Dominical
Manuel Antonio

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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 10 airlines flying from O'Hare Intl to San José

Discover the top 10 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 July 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
AviancaCheapest$148Average$670FlexibilityNo cancel feeOn-time71%
DeltaCheapest$221Average$482FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$271Average$796FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$303Average$488FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$309Average$661FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$339Average$555FlexibilityNo cancel feeOn-time71%
GOLCheapest$384Average$740FlexibilityNo cancel feeOn-time74%
United AirlinesCheapest$385Average$595FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$386Average$484FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$390Average$575FlexibilityNo cancel feeOn-time62%

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