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$142+ Cheap flights from Chicago (CHI) 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Apr 27 — May 41
Sun 4/27
Sun 5/4
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to San José Juan Santamaria Intl are usually found in May or July, booked 26 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

Cheap flight deals from Chicago to San José

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 April 22, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$332
(Cheapflightsfares)

One-way from

$142
(Mytrip)

Popular in

December

Cheapest in

May

Average price

$646

Good round-trip deal

$550 or less

Good one-way deal

$245 or less
Provider with most accurate pricing for Chicago (CHI)-San José Juan Santamaria Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-San José Juan Santamaria Intl flights.
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From Chicago (CHI) to San José Juan Santamaria Intl
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One-way flight from Chicago (CHI) to San José Juan Santamaria Intl
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Highest demand for flights based on searches. 10% potential increase in price ($74 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Chicago (CHI) to San José Juan Santamaria Intl.
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Price to beat on a one-way flight from Chicago (CHI) to San José Juan Santamaria Intl.
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Find flight deals from Chicago to San José

Cheapest flights from Chicago to San José
Explore the most affordable flight options available from Chicago to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/97:35 pmORD - SJO
1 stop16h 58mSpirit Airlines
Tue 5/1312:28 pmSJO - ORD
1 stop9h 36mSpirit Airlines
Deal found 4/22$328
This CheapOair deal was found by Cheapflights users on 4/21. 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.
Thu 6/57:35 pmORD - SJO
1 stop16h 58mMultiple Airlines
Mon 6/92:48 pmSJO - ORD
1 stop13h 54mMultiple Airlines
Deal found 4/21$334
This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/43:45 pmORD - SJO
2 stops17h 55mAvianca
Sat 6/75:05 amSJO - ORD
1 stop10h 00mAvianca
Deal found 4/22$367
This Copa Airlines deal was found by Cheapflights users on 4/22. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/46:56 amORD - SJO
1 stop12h 00mCopa Airlines
Tue 11/114:13 amSJO - ORD
1 stop8h 09mCopa Airlines
Deal found 4/22$387
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Mon 6/29:12 pmMDW - SJO
1 stop14h 15mMultiple Airlines
Mon 6/95:52 amSJO - MDW
2 stops12h 39mMultiple Airlines
Deal found 4/22$420
This United Airlines deal was found by Cheapflights users on 4/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/177:35 amORD - SJO
1 stop13h 02mUnited Airlines
Sat 5/241:00 pmSJO - ORD
Nonstop5h 34mUnited Airlines
Deal found 4/21$432
This Southwest deal was found by Cheapflights users on 4/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/55:05 amMDW - SJO
1 stop8h 40mSouthwest
Fri 9/191:40 pmSJO - MDW
1 stop9h 25mSouthwest
Deal found 4/22$437
This Delta deal was found by Cheapflights users on 4/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/265:30 amORD - SJO
1 stop8h 58mDelta
Sat 5/32:53 pmSJO - ORD
1 stop8h 06mDelta
Deal found 4/22$443
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/36:00 amMDW - SJO
1 stop6h 48mDelta
Mon 9/81:18 pmSJO - MDW
1 stop7h 26mDelta
Deal found 4/21$446
This American Airlines deal was found by Cheapflights users on 4/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/226:00 amORD - SJO
1 stop17h 04mAmerican Airlines
Sun 4/276:05 amSJO - ORD
1 stop16h 49mAmerican Airlines
Deal found 4/22$448

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago 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 April 22, 2025.
Use the filters below to find and compare flights from Chicago to San José that are best for you.

Fly from

Chicago

Fly to

San José

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 5/9

7:35 pm-11:33 am

1 stop16h 58m

San José Juan Santamaria Intl

Tue 5/13

12:28 pm-11:04 pm

1 stop9h 36m

$328

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 6/5

7:35 pm-11:33 am

1 stop16h 58m

San José Juan Santamaria Intl

Mon 6/9

2:48 pm-5:42 am

1 stop13h 54m

$334

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 6/4

3:45 pm-8:40 am

2 stops17h 55m

San José Juan Santamaria Intl

Sat 6/7

5:05 am-4:05 pm

1 stop10h 00m

$367

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 7/3

3:07 pm-7:35 am

1 stop17h 28m

San José Juan Santamaria Intl

Sun 7/6

8:09 am-11:52 pm

1 stop14h 43m

$410

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 6/2

9:12 pm-10:27 am

1 stop14h 15m

San José Juan Santamaria Intl

Mon 6/9

5:52 am-7:31 pm

2 stops12h 39m

$420

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 5/17

7:35 am-7:37 pm

1 stop13h 02m

San José Juan Santamaria Intl

Sat 5/24

1:00 pm-7:34 pm

Nonstop5h 34m

$432

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 4/26

5:30 am-1:28 pm

1 stop8h 58m

San José Juan Santamaria Intl

Sat 5/3

2:53 pm-11:59 pm

1 stop8h 06m

$443

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 4/27

8:27 am-6:24 pm

2 stops10h 57m

San José Juan Santamaria Intl

Sat 5/3

6:05 am-7:29 pm

2 stops12h 24m

$448

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 6/3

5:55 am-12:10 pm

1 stop7h 15m

San José Juan Santamaria Intl

Mon 6/9

8:45 am-9:25 pm

2 stops11h 40m

$490

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 4/26

6:04 am-1:28 pm

1 stop8h 24m

San José Juan Santamaria Intl

Sat 5/3

1:20 pm-10:22 pm

1 stop8h 02m

$507

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 23 results
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Compare providers for flights from Chicago 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 Chicago to San José in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*2 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 Chicago-San José, San José Province flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago-San José, San José Province flight deals on Cheapflights vs. AranGrant >95% of the time. Price accuracy is based on data collected from Chicago-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-San José, San José Province flights, Cheapflights users trust AranGrant the most. AranGrant 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-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 Chicago to San José

Have a flexible travel schedule? Discover the best time to fly to San José from Chicago 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 to San José

How far ahead should I book a flight from Chicago to San José, San José Province?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to San José. Price data was last updated on April 18, 2025.

The best time to book flights from Chicago to San José, San José Province is 26 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 to San José, San José Province?

Currently, September is the cheapest month in which you can book a flight from Chicago to San José, San José Province (average of $398). Flying from Chicago to San José, San José Province in March is currently the most expensive (average of $555). 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 CHI to SJO?

Find hourly flight availability from Chicago 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 April 22, 2025.

One of the essential ways to save on airfare from Chicago to San José, San José Province is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 47% on airfare.

What is the cheapest day to fly from Chicago to San José, San José Province?

Use this chart to determine the cheapest time to fly round-trip from Chicago to San José. Price data was last updated on December 16, 2024.

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

Rainfall in San José by month

Plan your trip to San José by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San José, San José Province ranges from 0.0 - 11.8 inches per month. September is typically the wettest month, when rainfall can reach 11.8 in. February is typically the driest time to visit San José, San José Province when rainfall is around 0.0 in.

Temperature in San José by month

Plan your trip to San José by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San José, San José Province, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 64.4 F).

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 April 22, 2025.
See what other customers who have flown with Southwest, Delta and Copa Airlines from Chicago 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
8.0
Very good
4,286 reviews

Overall

8.0

Food

7.1

Crew

8.6

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Overall

8.0

Food

7.1

Crew

8.6

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,286 reviews

Overall

8.0

Food

7.1

Crew

8.6

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Copa Airlines
7.5
Good
1,408 reviews
Southwest
8.0
Very good
4,286 reviews

Overall

8.0

Food

7.1

Crew

8.6

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Aeromexico
7.5
Good
1,700 reviews
Southwest
8.0
Very good
4,286 reviews

Overall

8.0

Food

7.1

Crew

8.6

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,683 reviews
Southwest
8.0
Very good
4,286 reviews

Overall

8.0

Food

7.1

Crew

8.6

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Related info for your journey

Find useful and relevant information for your journey from Chicago 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?

    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. Booking flights from Chicago to Juan Santamaria Intl (SJO) should be relatively easy as there are 0 daily inbound flights from Chicago from 8 different airlines.

  • What are the cheapest airlines flying from Chicago to San José, San José Province round-trip?

    Currently priced at $332, Spirit Airlines will fly you from Chicago to San José, San José Province and back. In addition to Spirit Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Avianca and Copa Airlines - these airlines can fly you to your destination from $367 and $410, respectively. Spirit Airlines is currently priced 44% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Chicago to San José, San José Province one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $142. However, be on the lookout for offers from Frontier and Delta, as they are both options that can get you from Chicago to San José, San José Province for a low price.

  • What are the cheapest flights from Chicago to San José, San José Province?

    The cheapest flight price from Chicago to San José, San José Province is $200. On average you can expect to pay $536. The most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), can usually be booked for $285.

  • Where are the most common layover locations when flying from Chicago to San José, San José Province?

    Most of the time, Chicago to San José, San José Province flights that have layovers will stop in Fort Lauderdale. Orlando follows Fort Lauderdale in terms of the most common layover location on Chicago to San José, San José Province flights.

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

    Most Fort Lauderdale visitors opt to spend their time experiencing Las Olas Beach, Port Everglades, and Fort Lauderdale Beach Park. Las Olas Beach, Port Everglades and Fort Lauderdale Beach Park are located about 4.1 mi, 2.1 mi, and 4.2 mi, respectively from Fort Lauderdale if you are interested in checking them out. Those looking to explore during their layover in Fort Lauderdale can rent a car from Fort Lauderdale for about $27 per day.

  • What are some popular points of interest to see during a layover in Orlando?

    The majority of Orlando visitors spend their time at Walt Disney World Resort, Universal Orlando Resort, and International Drive. Those on a layover in Orlando interested in visiting Walt Disney World Resort, Universal Orlando Resort, or International Drive can do so by traveling 16.2 mi, 10.2 mi, and 9.9 mi, respectively from Orlando. Those looking to explore during their layover in Orlando can rent a car from Orlando for about $26 per day.

  • Where are the least popular layover locations for Chicago to San José, San José Province flights?

    Chicago to San José, San José Province flights have a layover in Panama City the least frequently.

  • Can I find deals for flights from Chicago to San José that include hotel bookings?

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

  • How can I find direct flights from Chicago to San José?

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

  • Can I find deals for business class flights from Chicago to San José?

    Yes. Cheapflights offers flight deals from Chicago 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 to San José, San José Province?

    Currently, September is the cheapest month in which you can book a flight from Chicago to San José, San José Province (average of $398). Flying from Chicago to San José, San José Province in March is currently the most expensive (average of $555). 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

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Top 8 airlines flying from Chicago to San José

Discover the top 8 airlines that operate flights from Chicago 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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$245Average$416FlexibilityNo cancel feeOn-time65%
AviancaCheapest$337Average$489FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$345Average$635FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$416Average$616FlexibilityNo cancel feeOn-time70%
DeltaCheapest$442Average$777FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$480Average$696FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$540Average$630FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$548Average$779FlexibilityNo cancel feeOn-time69%

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