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O'Hare Intl

$200+ 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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — ORD
Jun 13 — Jun 201
Sat 6/13
Sat 6/20
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

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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 January, booked 90 days in advance, depart on a Tuesday or Thursday 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 May 14, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 5/13. 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.
Tue 9/12:02 pm
SJO
-
ORD
1 stop8h 42m
JetBlue
Tue 9/87:00 am
ORD
-
SJO
1 stop6h 57m
JetBlue
Deal found 5/13$348
This Expedia deal was found by Cheapflights users on 5/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:35 am
SJO
-
ORD
1 stop12h 39m
Multiple Airlines
Mon 8/317:00 am
ORD
-
SJO
1 stop6h 57m
Multiple Airlines
Deal found 5/11$354
This CheapOair deal was found by Cheapflights users on 5/11. 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 8/229:35 am
SJO
-
ORD
1 stop12h 39m
Multiple Airlines
Mon 8/317:00 am
ORD
-
SJO
1 stop6h 57m
Multiple Airlines
Deal found 5/11$361
This CheapOair deal was found by Cheapflights users on 5/9. 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.
Fri 8/219:35 am
SJO
-
ORD
1 stop12h 39m
Frontier
Wed 8/265:30 pm
ORD
-
SJO
1 stop15h 50m
Frontier
Deal found 5/9$365
This CheapOair deal was found by Cheapflights users on 5/11. 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 8/159:35 am
SJO
-
ORD
1 stop12h 30m
Multiple Airlines
Wed 8/197:00 am
ORD
-
SJO
1 stop6h 57m
Multiple Airlines
Deal found 5/11$366
This Orbitz deal was found by Cheapflights users on 5/11. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:35 am
SJO
-
ORD
1 stop12h 30m
Frontier
Sat 8/85:13 pm
ORD
-
SJO
1 stop16h 07m
Frontier
Deal found 5/11$370
This Cheapflightsfares deal was found by Cheapflights users on 5/12. 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 8/272:02 pm
SJO
-
ORD
1 stop8h 42m
JetBlue
Sun 8/307:00 am
ORD
-
SJO
1 stop6h 57m
JetBlue
Deal found 5/12$375
This Expedia deal was found by Cheapflights users on 5/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:02 pm
SJO
-
ORD
1 stop8h 42m
Multiple Airlines
Sat 9/55:30 pm
ORD
-
SJO
1 stop15h 50m
Multiple Airlines
Deal found 5/11$381
This JetBlue deal was found by Cheapflights users on 5/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:02 pm
SJO
-
ORD
1 stop8h 42m
JetBlue
Wed 9/27:00 am
ORD
-
SJO
1 stop6h 57m
JetBlue
Deal found 5/11$384
This Cheapflightsfares deal was found by Cheapflights users on 5/12. 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.
Fri 8/282:02 pm
SJO
-
ORD
1 stop8h 42m
JetBlue
Sun 8/307:00 am
ORD
-
SJO
1 stop6h 57m
JetBlue
Deal found 5/12$388
This Expedia deal was found by Cheapflights users on 5/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:35 am
SJO
-
ORD
1 stop12h 30m
Frontier
Wed 8/55:13 pm
ORD
-
SJO
1 stop16h 07m
Frontier
Deal found 5/9$391

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 May 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$348
(Cheapflightsfares)

One-way from

$200
(Super.com)

Popular in

March

Cheapest in

February

Average price

$480

Good round-trip deal

$494 or less

Good one-way deal

$202 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. 5% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 14, 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

Price

Cheapest round-trip
Quickest round-trip

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 8/11

2:02 pm-11:44 pm

1 stop8h 42m

Chicago O'Hare Intl

Tue 8/25

7:00 am-12:57 pm

1 stop6h 57m

$427

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 9/22

4:15 pm-12:09 pm

1 stop18h 54m

Chicago O'Hare Intl

Mon 9/28

2:53 am-11:59 pm

1 stop22h 06m

$447

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 10/2

10:03 am-12:57 am

1 stop13h 54m

Chicago O'Hare Intl

Fri 10/9

3:20 pm-8:19 am

1 stop17h 59m

$473

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 10/27

8:48 am-1:24 am

1 stop15h 36m

Chicago O'Hare Intl

Sat 10/31

3:13 pm-7:06 am

1 stop16h 53m

$473

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sun 8/16

5:55 pm-1:59 pm

1 stop19h 04m

Chicago O'Hare Intl

Thu 8/20

8:02 am-6:59 pm

1 stop11h 57m

$473

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sun 11/1

6:08 pm-12:46 pm

1 stop18h 38m

Chicago O'Hare Intl

Thu 11/5

7:35 am-5:01 pm

1 stop9h 26m

$473

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 7/15

4:08 am-1:57 pm

1 stop8h 49m

Chicago O'Hare Intl

Mon 7/20

3:21 pm-7:12 am

1 stop16h 51m

$473

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sun 9/13

5:45 am-1:02 am

1 stop18h 17m

Chicago O'Hare Intl

Sat 9/19

3:20 pm-9:04 am

1 stop18h 44m

$473

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sun 8/23

10:03 am-1:02 am

1 stop13h 59m

Chicago O'Hare Intl

Mon 8/31

3:21 pm-7:10 am

1 stop16h 49m

$473

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 7/9

8:45 am-4:00 am

1 stop18h 15m

Chicago O'Hare Intl

Thu 7/23

3:21 pm-7:12 am

1 stop16h 51m

$473

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/13

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 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 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.
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?

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 $386). Flying from San José to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $559). 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 May 14, 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 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 May 14, 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.
Copa Airlines
7.5
Good
1,584 reviews

Entertainment

6.8

Comfort

7.4

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2026

LIM - PTY

Fast boarding, polite and helpful staff. Lowest cost across all airlines
Copa Airlines
7.5
Good
1,584 reviews
Copa Airlines
7.5
Good
1,584 reviews

Entertainment

6.8

Comfort

7.4

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2026

LIM - PTY

Fast boarding, polite and helpful staff. Lowest cost across all airlines
United Airlines
7.4
Good
9,711 reviews
Copa Airlines
7.5
Good
1,584 reviews

Entertainment

6.8

Comfort

7.4

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2026

LIM - PTY

Fast boarding, polite and helpful staff. Lowest cost across all airlines
American Airlines
7.1
Good
11,666 reviews
Copa Airlines
7.5
Good
1,584 reviews

Entertainment

6.8

Comfort

7.4

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2026

LIM - PTY

Fast boarding, polite and helpful staff. Lowest cost across all airlines
Avianca
6.5
Okay
2,523 reviews
Copa Airlines
7.5
Good
1,584 reviews

Entertainment

6.8

Comfort

7.4

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2026

LIM - PTY

Fast boarding, polite and helpful staff. Lowest cost across all airlines
Spirit Airlines
6.3
Okay
8,629 reviews
Copa Airlines
7.5
Good
1,584 reviews

Entertainment

6.8

Comfort

7.4

Food

6.8

Boarding

7.8

Overall

7.5

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2026

LIM - PTY

Fast boarding, polite and helpful staff. Lowest cost across all airlines

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 0 outbound flights 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 JetBlue and Copa Airlines fly from San José to Chicago O'Hare Intl Airport in about 8h 42m. The time it takes to get you to your destination can typically vary by up to 6h 35m. 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 $179 on this airline. Additional options worth looking into are Copa Airlines and Avianca, starting at $189 and $249 round-trip. Spirit Airlines is currently priced 62% 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $172. American Airlines flights start at $183 while deals on Copa Airlines start at $198 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 $192. On average you can expect to pay $406. The most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl), can usually be booked for $313.

  • 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, February is the cheapest month in which you can book a flight from San José to Chicago O'Hare Intl Airport (average of $386). Flying from San José to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $559). 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
Rosemont
Schaumburg
Naperville
Benton Harbor
Delavan
Oakbrook Terrace
Lake Geneva
Gurnee
Downers Grove
Des Plaines
Hoffman Estates
Oak Brook
South Holland
Libertyville
Warrenville
Elk Grove Village
Bridgeview
Great Lakes
Arlington Heights
Northbrook

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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

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 May 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$179Average$292FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$189Average$458FlexibilityNo cancel feeOn-time70%
AviancaCheapest$249Average$461FlexibilityNo cancel feeOn-time71%
American AirlinesCheapest$332Average$510FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$370Average$469FlexibilityNo cancel feeOn-time69%

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