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San José

$132+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$332
(Kiwi.com)

One-way from

$132
(Mytrip)

Popular in

December

Cheapest in

May

Average price

$690

Good round-trip deal

$635 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. 11% potential increase in price ($77 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 March 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 March 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 3/26. 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 5/114:15 pmORD - SJO
1 stop19h 12mMultiple Airlines
Sun 5/1812:28 pmSJO - ORD
2 stops34h 04mMultiple Airlines
Deal found 3/26$332
This Mytrip deal was found by Cheapflights users on 3/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/97:47 amORD - SJO
1 stop27h 40mSpirit Airlines
Mon 5/1211:32 amSJO - ORD
3 stops35h 52mSpirit Airlines
Deal found 3/27$333
This Cheapflightsfares deal was found by Cheapflights users on 3/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/63:45 pmORD - SJO
1 stop7h 05mAvianca
Mon 6/97:45 pmSJO - ORD
1 stop19h 20mAvianca
Deal found 3/28$337
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Wed 4/912:46 pmMDW - SJO
1 stop22h 38mMultiple Airlines
Wed 4/1611:35 amSJO - MDW
1 stop20h 49mMultiple Airlines
Deal found 3/27$391
This KAYAK deal was found by Cheapflights users on 3/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/143:07 pmORD - SJO
1 stop17h 28mCopa Airlines
Sun 6/226:07 pmSJO - ORD
1 stop18h 40mCopa Airlines
Deal found 3/27$419
This American Airlines deal was found by Cheapflights users on 3/27. 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.
Sat 5/107:00 amORD - SJO
1 stop7h 09mAmerican Airlines
Sat 5/176:03 amSJO - ORD
1 stop16h 53mAmerican Airlines
Deal found 3/27$443
This Delta deal was found by Cheapflights users on 3/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/292:30 pmORD - SJO
1 stop7h 54mDelta
Thu 4/37:00 amSJO - ORD
2 stops10h 19mDelta
Deal found 3/28$447
This Southwest deal was found by Cheapflights users on 3/26. 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.
Wed 5/78:40 amMDW - SJO
2 stops12h 00mSouthwest
Wed 5/148:45 amSJO - MDW
2 stops11h 20mSouthwest
Deal found 3/26$470
This CheapOair deal was found by Cheapflights users on 3/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/26:00 amMDW - SJO
1 stop7h 35mFrontier
Sat 8/91:47 pmSJO - MDW
1 stop8h 34mFrontier
Deal found 3/28$471
This Delta deal was found by Cheapflights users on 3/27. 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 4/196:04 amMDW - SJO
1 stop8h 24mDelta
Sat 4/261:20 pmSJO - MDW
1 stop8h 02mDelta
Deal found 3/27$555

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 March 28, 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

Sun 5/11

4:15 pm-10:27 am

1 stop19h 12m

San José Juan Santamaria Intl

Sun 5/18

12:28 pm-11:32 pm

2 stops34h 04m

$332

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 5/9

7:47 am-10:27 am

1 stop27h 40m

San José Juan Santamaria Intl

Mon 5/12

11:32 am-12:24 am

3 stops35h 52m

$333

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 6/6

3:45 pm-9:50 pm

1 stop7h 05m

San José Juan Santamaria Intl

Mon 6/9

7:45 pm-4:05 pm

1 stop19h 20m

$337

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 4/9

12:46 pm-10:24 am

1 stop22h 38m

San José Juan Santamaria Intl

Wed 4/16

11:35 am-9:24 am

1 stop20h 49m

$391

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 6/14

3:07 pm-7:35 am

1 stop17h 28m

San José Juan Santamaria Intl

Sun 6/22

6:07 pm-1:47 pm

1 stop18h 40m

$419

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 5/7

5:30 am-11:59 am

1 stop7h 29m

San José Juan Santamaria Intl

Sat 5/24

2:30 pm-11:17 pm

1 stop7h 47m

$443

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 5/10

8:05 am-10:24 pm

1 stop15h 19m

San José Juan Santamaria Intl

Sat 5/17

6:03 am-11:56 pm

1 stop16h 53m

$446

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 5/7

8:40 am-7:40 pm

2 stops12h 00m

San José Juan Santamaria Intl

Wed 5/14

8:45 am-9:05 pm

2 stops11h 20m

$470

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 8/2

6:00 am-12:35 pm

1 stop7h 35m

San José Juan Santamaria Intl

Sat 8/9

1:47 pm-11:21 pm

1 stop8h 34m

$471

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 4/19

6:04 am-1:28 pm

1 stop8h 24m

San José Juan Santamaria Intl

Sat 4/26

1:20 pm-10:22 pm

1 stop8h 02m

$555

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Showing 1-10 of 24 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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star
Justfly.comPrice 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.

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 March 21, 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 March 28, 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 48% 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 March 28, 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
4,273 reviews

Overall

8.1

Food

7.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Overall

8.1

Food

7.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Alaska Airlines
8.0
Very good
9,798 reviews
Southwest
8.1
Very good
4,273 reviews

Overall

8.1

Food

7.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,896 reviews
Southwest
8.1
Very good
4,273 reviews

Overall

8.1

Food

7.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Copa Airlines
7.5
Good
1,395 reviews
Southwest
8.1
Very good
4,273 reviews

Overall

8.1

Food

7.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,603 reviews
Southwest
8.1
Very good
4,273 reviews

Overall

8.1

Food

7.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $333, 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 $337 and $419, 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 $132. However, be on the lookout for offers from Avianca and United 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 $245. On average you can expect to pay $571. The most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), can usually be booked for $230.

  • 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 $28 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 $29 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$237Average$405FlexibilityNo cancel feeOn-time65%
AviancaCheapest$337Average$475FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$345Average$623FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$430Average$620FlexibilityNo cancel feeOn-time70%
DeltaCheapest$447Average$787FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$540Average$628FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$542Average$699FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$569Average$780FlexibilityNo cancel feeOn-time69%
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