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$88+ 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 3/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Chicago to San José Juan Santamaria Intl are usually found in May or June, booked 32 days in advance, depart on a Tuesday or Thursday 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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$329
(CheapOair)

One-way from

$88
(Cheapflightsfares)

Popular in

December

Cheapest in

May

Average price

$637

Good round-trip deal

$696 or less

Good one-way deal

$300 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
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($71 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/15:45 pmORD - SJO
1 stop17h 39mSpirit Airlines
Tue 3/1812:50 amSJO - ORD
2 stops17h 06mSpirit Airlines
Deal found 2/19$327
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/247:25 amMDW - SJO
2 stops28h 56mMultiple Airlines
Tue 4/111:55 amSJO - MDW
1 stop10h 29mMultiple Airlines
Deal found 2/19$331
This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2412:48 amORD - SJO
1 stop13h 09mMultiple Airlines
Wed 3/51:50 amSJO - ORD
1 stop14h 37mMultiple Airlines
Deal found 2/19$332
This JetBlue deal was found by Cheapflights users on 2/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2811:44 amORD - SJO
1 stop10h 04mJetBlue
Tue 3/411:44 pmSJO - ORD
1 stop10h 59mJetBlue
Deal found 2/19$431
This Copa Airlines deal was found by Cheapflights users on 2/20. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/153:09 pmORD - SJO
1 stop17h 25mCopa Airlines
Thu 3/205:51 amSJO - ORD
1 stop17h 36mCopa Airlines
Deal found 2/20$436
This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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.
Fri 2/281:35 pmORD - SJO
1 stop19h 45mAvianca
Mon 3/32:15 amSJO - ORD
1 stop10h 00mAvianca
Deal found 2/19$460
This Southwest deal was found by Cheapflights users on 2/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/287:50 amMDW - SJO
2 stops12h 50mSouthwest
Tue 5/131:10 pmSJO - MDW
1 stop8h 40mSouthwest
Deal found 2/19$519
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/612:44 pmMDW - SJO
1 stop9h 28mDelta
Sat 3/82:19 pmSJO - MDW
1 stop8h 01mDelta
Deal found 2/19$520

Find flights from Chicago to San José within your budget

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 February 20, 2025.

Fly from

Chicago

Fly to

San José

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 3/1

5:45 pm-11:24 am

1 stop17h 39m

San José Juan Santamaria Intl

Tue 3/18

12:50 am-6:56 pm

2 stops17h 06m

$327

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 3/24

7:25 am-11:21 am

2 stops28h 56m

San José Juan Santamaria Intl

Tue 4/1

11:55 am-11:24 pm

1 stop10h 29m

$331

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 5/6

5:10 am-11:18 am

1 stop7h 08m

San José Juan Santamaria Intl

Fri 5/16

1:41 pm-11:32 pm

1 stop8h 51m

$331

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 2/28

11:44 am-9:48 pm

1 stop10h 04m

San José Juan Santamaria Intl

Tue 3/4

11:44 pm-10:43 am

1 stop10h 59m

$431

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 3/15

3:09 pm-7:34 am

1 stop17h 25m

San José Juan Santamaria Intl

Thu 3/20

5:51 am-12:27 am

1 stop17h 36m

$436

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 2/28

1:35 pm-9:20 am

1 stop19h 45m

San José Juan Santamaria Intl

Mon 3/3

2:15 am-12:15 pm

1 stop10h 00m

$460

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 4/28

7:50 am-7:40 pm

2 stops12h 50m

San José Juan Santamaria Intl

Tue 5/13

1:10 pm-10:50 pm

1 stop8h 40m

$519

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 3/6

12:44 pm-10:12 pm

1 stop9h 28m

San José Juan Santamaria Intl

Sat 3/8

2:19 pm-10:20 pm

1 stop8h 01m

$520

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 3/26

9:08 pm-10:25 am

1 stop14h 17m

$88

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 3/25

6:25 am-11:50 pm

2 stops18h 25m

$94

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 23 results
1
2
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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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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 Chicago-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-San José, San José Province flight deals on Cheapflights vs. FlightHub >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 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-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.

Travel insights for flights from Chicago to San José

Get recent, data-driven insights about flights from Chicago to San José including ideal travel times, pricing trends, and more.

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 February 14, 2025.

The best time to book flights from Chicago to San José, San José Province is 32 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 February 20, 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 afternoon 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 February 20, 2025.
See what other customers who have flown with Southwest, Alaska Airlines and Delta 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
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Copa Airlines
7.6
Good
1,510 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $330, 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 Copa Airlines and JetBlue - these airlines can fly you to your destination from $436 and $440, respectively. Spirit Airlines is currently priced 45% 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 $88. However, be on the lookout for offers from JetBlue and Copa Airlines, 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 $300. On average you can expect to pay $1,225. The most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), can usually be booked for $236.

  • 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 $26 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 $27 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.

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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$238Average$393FlexibilityNo cancel feeOn-time65%
AviancaCheapest$337Average$469FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$345Average$623FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$459Average$642FlexibilityNo cancel feeOn-time70%
DeltaCheapest$517Average$752FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$540Average$618FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$565Average$717FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$582Average$798FlexibilityNo cancel feeOn-time69%
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