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O'Hare Intl

$129+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — ORD
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
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 San José Juan Santamaria Intl to Chicago O'Hare Intl are usually found in February or September, booked 58 days in advance, depart on a Thursday or Tuesday and return on a Tuesday

Cheap 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 January 21, 2026.

This OneTravel deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/61:30 pm
SJO
-
ORD
1 stop10h 17m
Spirit Airlines
Sun 2/157:00 am
ORD
-
SJO
1 stop29h 22m
Spirit Airlines
Deal found 1/20$257
This OneTravel deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/131:31 pm
SJO
-
ORD
1 stop10h 16m
Spirit Airlines
Sun 3/18:59 am
ORD
-
SJO
2 stops26h 41m
Spirit Airlines
Deal found 1/19$261
This Cheapflightsfares deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/141:31 pm
SJO
-
ORD
1 stop10h 16m
Spirit Airlines
Sun 3/15:15 am
ORD
-
SJO
1 stop7h 07m
Spirit Airlines
Deal found 1/19$262
This Cheapflightsfares deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/181:31 pm
SJO
-
ORD
1 stop7h 42m
Spirit Airlines
Wed 2/255:15 am
ORD
-
SJO
1 stop7h 07m
Spirit Airlines
Deal found 1/19$264
This Cheapflightsfares deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/181:31 pm
SJO
-
ORD
1 stop7h 42m
Spirit Airlines
Mon 2/238:16 pm
ORD
-
SJO
1 stop16h 06m
Spirit Airlines
Deal found 1/20$266
This Cheapflightsfares deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/51:30 pm
SJO
-
ORD
1 stop10h 17m
Spirit Airlines
Sun 2/225:15 am
ORD
-
SJO
1 stop7h 07m
Spirit Airlines
Deal found 1/20$267
This FlightHub deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1812:35 pm
SJO
-
ORD
2 stops11h 12m
Spirit Airlines
Tue 2/245:15 am
ORD
-
SJO
1 stop7h 07m
Spirit Airlines
Deal found 1/20$271
This Kiwi.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/61:30 pm
SJO
-
ORD
1 stop10h 17m
Multiple Airlines
Sun 2/153:40 pm
ORD
-
SJO
2 stops20h 00m
Multiple Airlines
Deal found 1/20$272
This Kiwi.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/131:31 pm
SJO
-
ORD
1 stop9h 32m
Multiple Airlines
Sat 2/288:05 am
ORD
-
SJO
2 stops28h 17m
Multiple Airlines
Deal found 1/20$273
This Kiwi.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/51:30 pm
SJO
-
ORD
1 stop9h 06m
Multiple Airlines
Sun 2/153:40 pm
ORD
-
SJO
2 stops20h 00m
Multiple Airlines
Deal found 1/20$274

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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$257
(OneTravel)

One-way from

$129
(CheapOair)

Popular in

June

Cheapest in

February

Average price

$411

Good round-trip deal

$296 or less

Good one-way deal

$150 or less
Provider with most accurate pricing for San José Juan Santamaria Intl-Chicago O'Hare Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-Chicago O'Hare Intl flights.
Search Deals
From San José Juan Santamaria Intl to Chicago O'Hare Intl
Search Deals
One-way flight from San José Juan Santamaria Intl to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from San José Juan Santamaria Intl to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from San José Juan Santamaria Intl to Chicago O'Hare Intl.
Search Deals

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 January 21, 2026.
Use the filters below to find and compare flights from San José to Chicago O'Hare Intl Airport that are best for you.

Fly from

San José

Fly to

O'Hare Intl

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 2/14

1:31 pm-11:47 pm

1 stop10h 16m

Chicago O'Hare Intl

Sat 2/21

8:59 am-11:40 am

2 stops26h 41m

$282

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 2/28

8:07 am-7:54 am

2 stops23h 47m

Chicago O'Hare Intl

Wed 3/4

8:16 pm-3:20 pm

2 stops19h 04m

$310

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 2/4

7:45 am-8:18 am

1 stop24h 33m

Chicago O'Hare Intl

Sun 2/8

6:57 pm-3:30 pm

1 stop20h 33m

$312

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 2/6

12:33 pm-11:47 pm

2 stops11h 14m

Chicago O'Hare Intl

Sun 2/15

7:00 am-11:40 am

2 stops28h 40m

$325

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 2/5

2:05 pm-7:35 pm

Nonstop5h 30m

Chicago O'Hare Intl

Sun 2/8

7:39 am-12:56 pm

Nonstop5h 17m

$340

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Mon 2/9

2:05 pm-7:35 pm

Nonstop5h 30m

Chicago O'Hare Intl

Sun 2/22

7:35 am-8:39 pm

1 stop13h 04m

$340

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

Sat 2/28

6:20 pm-6:25 am

1 stop12h 05m

$340

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Mon 2/2

2:05 pm-7:35 pm

Nonstop5h 30m

Chicago O'Hare Intl

Tue 2/3

7:50 pm-1:15 pm

1 stop17h 25m

$340

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

Wed 2/18

7:35 am-8:39 pm

1 stop13h 04m

$340

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sun 3/8

5:50 am-1:04 am

1 stop18h 14m

Chicago O'Hare Intl

Sun 3/15

3:22 pm-7:05 am

1 stop16h 43m

$342

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 23 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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 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 Expedia the most. Expedia 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 January 16, 2026.

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 58 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 $338). 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 January 21, 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.

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 January 21, 2026.
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
1,557 reviews

Crew

8.1

Food

6.8

Entertainment

6.8

Boarding

7.8

Comfort

7.4

Overall

7.6

Reviews

1 / 20
2.0
Mediocre

Maria,Dec 2025

PTY - SLA

Old plain no entertainment , no outlet for cell or computer! And online they said you have all that! Almost 6 hrs looking to the floor..terrible expirencw and I pay a lot of money for it
Copa Airlines
7.6
Good
1,557 reviews
Copa Airlines
7.6
Good
1,557 reviews

Crew

8.1

Food

6.8

Entertainment

6.8

Boarding

7.8

Comfort

7.4

Overall

7.6

Reviews

1 / 20
2.0
Mediocre

Maria,Dec 2025

PTY - SLA

Old plain no entertainment , no outlet for cell or computer! And online they said you have all that! Almost 6 hrs looking to the floor..terrible expirencw and I pay a lot of money for it
United Airlines
7.4
Good
9,190 reviews
Copa Airlines
7.6
Good
1,557 reviews

Crew

8.1

Food

6.8

Entertainment

6.8

Boarding

7.8

Comfort

7.4

Overall

7.6

Reviews

1 / 20
2.0
Mediocre

Maria,Dec 2025

PTY - SLA

Old plain no entertainment , no outlet for cell or computer! And online they said you have all that! Almost 6 hrs looking to the floor..terrible expirencw and I pay a lot of money for it
American Airlines
7.2
Good
11,173 reviews
Copa Airlines
7.6
Good
1,557 reviews

Crew

8.1

Food

6.8

Entertainment

6.8

Boarding

7.8

Comfort

7.4

Overall

7.6

Reviews

1 / 20
2.0
Mediocre

Maria,Dec 2025

PTY - SLA

Old plain no entertainment , no outlet for cell or computer! And online they said you have all that! Almost 6 hrs looking to the floor..terrible expirencw and I pay a lot of money for it
Avianca
6.6
Okay
2,496 reviews
Copa Airlines
7.6
Good
1,557 reviews

Crew

8.1

Food

6.8

Entertainment

6.8

Boarding

7.8

Comfort

7.4

Overall

7.6

Reviews

1 / 20
2.0
Mediocre

Maria,Dec 2025

PTY - SLA

Old plain no entertainment , no outlet for cell or computer! And online they said you have all that! Almost 6 hrs looking to the floor..terrible expirencw and I pay a lot of money for it
Spirit Airlines
6.3
Okay
8,365 reviews
Copa Airlines
7.6
Good
1,557 reviews

Crew

8.1

Food

6.8

Entertainment

6.8

Boarding

7.8

Comfort

7.4

Overall

7.6

Reviews

1 / 20
2.0
Mediocre

Maria,Dec 2025

PTY - SLA

Old plain no entertainment , no outlet for cell or computer! And online they said you have all that! Almost 6 hrs looking to the floor..terrible expirencw and I pay a lot of money for it

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 5 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 Spirit 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 4h 46m. 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 $206 on this airline. Additional options worth looking into are Avianca and Copa Airlines, starting at $249 and $311 round-trip. Spirit Airlines is currently priced 53% below the average price you’ll pay for this route.

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

    To fly one-way, consider booking your trip with Avianca, which is currently one of the cheapest options available, starting at $166. Spirit Airlines flights start at $179 while deals on American Airlines start at $183 one-way.

  • 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 $141. On average you can expect to pay $290. The most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl), can usually be booked for $218.

  • 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 $338). 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
Naperville
Gurnee
Elgin
Hoffman Estates
Beloit
Delavan
Oak Brook
Downers Grove
Des Plaines
Elk Grove Village
Skokie
Libertyville
Lake Geneva
Bridgeview
Kenosha
Warrenville
Waukegan
Aurora

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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 5 airlines flying from San José to O'Hare Intl

Discover the top 5 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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$206Average$348FlexibilityNo cancel feeOn-time65%
AviancaCheapest$249Average$485FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$311Average$448FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$332Average$465FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$400Average$502FlexibilityNo cancel feeOn-time69%

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