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San José

$152+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Mar 30 — Apr 61
Mon 3/30
Mon 4/6
1 adult, Economy
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Find cheap flights from Chicago to San José with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

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Cheapflights Tip: The best prices from Chicago to San José Juan Santamaria Intl are usually found in September or October, booked 14 days in advance, depart on a Tuesday or Monday and return on a Thursday

Cheap 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 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/25. 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.
Sat 4/251:27 pm
ORD
-
SJO
1 stop22h 48m
Multiple Airlines
Mon 5/1812:20 pm
SJO
-
ORD
1 stop10h 54m
Multiple Airlines
Deal found 2/25$322
This Mytrip deal was found by Cheapflights users on 2/25. 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.
Mon 3/912:58 am
ORD
-
SJO
1 stop13h 52m
Multiple Airlines
Tue 3/177:05 am
SJO
-
ORD
1 stop11h 58m
Multiple Airlines
Deal found 2/25$323
This Kiwi.com deal was found by Cheapflights users on 2/25. 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 5/275:05 am
ORD
-
SJO
1 stop7h 10m
Spirit Airlines
Tue 6/212:20 pm
SJO
-
ORD
1 stop10h 54m
Spirit Airlines
Deal found 2/25$325
This Cheapflightsfares deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:16 pm
ORD
-
SJO
1 stop16h 06m
Spirit Airlines
Sat 3/71:31 pm
SJO
-
ORD
1 stop7h 42m
Spirit Airlines
Deal found 2/25$326
This CheapOair deal was found by Cheapflights users on 2/24. 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.
Wed 4/155:05 am
ORD
-
SJO
1 stop7h 10m
Spirit Airlines
Wed 4/2212:20 pm
SJO
-
ORD
1 stop10h 54m
Spirit Airlines
Deal found 2/24$327
This Kiwi.com deal was found by Cheapflights users on 2/25. 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.
Sat 5/161:27 pm
ORD
-
SJO
1 stop22h 48m
Multiple Airlines
Thu 5/2812:20 pm
SJO
-
ORD
1 stop10h 54m
Multiple Airlines
Deal found 2/25$328
This Mytrip deal was found by Cheapflights users on 2/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/78:16 pm
ORD
-
SJO
1 stop15h 06m
Multiple Airlines
Sat 3/147:58 am
SJO
-
ORD
1 stop9h 33m
Multiple Airlines
Deal found 2/26$329
This Cheapflightsfares deal was found by Cheapflights users on 2/25. 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 5/55:05 am
ORD
-
SJO
1 stop7h 10m
Spirit Airlines
Wed 5/2012:20 pm
SJO
-
ORD
1 stop10h 54m
Spirit Airlines
Deal found 2/25$330
This Cheapflightsfares deal was found by Cheapflights users on 2/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:16 pm
ORD
-
SJO
1 stop16h 06m
Spirit Airlines
Mon 3/912:31 pm
SJO
-
ORD
1 stop10h 16m
Spirit Airlines
Deal found 2/26$331
This Cheapflightsfares deal was found by Cheapflights users on 2/25. 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.
Mon 4/135:05 am
ORD
-
SJO
1 stop7h 09m
Spirit Airlines
Sat 4/2512:20 pm
SJO
-
ORD
1 stop10h 54m
Spirit Airlines
Deal found 2/25$332
This Kiwi.com deal was found by Cheapflights users on 2/25. 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 4/261:22 pm
ORD
-
SJO
1 stop22h 53m
Multiple Airlines
Sat 5/1612:20 pm
SJO
-
ORD
1 stop10h 54m
Multiple Airlines
Deal found 2/25$333
This Cheapflightsfares deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:10 pm
ORD
-
SJO
1 stop18h 04m
Spirit Airlines
Thu 4/1612:20 pm
SJO
-
ORD
1 stop10h 54m
Spirit Airlines
Deal found 2/25$334

Find 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 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$322
(Kiwi.com)

One-way from

$152
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$469

Good round-trip deal

$423 or less

Good one-way deal

$335 or less
Provider with most accurate pricing for Chicago (CHI)-San José Juan Santamaria Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-San José Juan Santamaria Intl flights.
Search Deals
From Chicago (CHI) to San José Juan Santamaria Intl
Search Deals
One-way flight from Chicago (CHI) to San José Juan Santamaria Intl
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to San José Juan Santamaria Intl.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to San José Juan Santamaria Intl.
Search Deals

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 February 28, 2026.
Use the filters below to find and compare flights from Chicago to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 8/22

1:19 pm-11:27 am

2 stops23h 08m

San José Juan Santamaria Intl

Tue 9/1

12:32 pm-11:33 pm

1 stop10h 01m

$349

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 3/30

3:28 pm-8:20 am

1 stop17h 52m

San José Juan Santamaria Intl

Thu 4/2

2:20 pm-1:13 am

1 stop9h 53m

$430

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 3/24

8:34 am-7:01 pm

1 stop11h 27m

San José Juan Santamaria Intl

Tue 3/31

6:21 pm-1:50 pm

1 stop18h 29m

$430

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 4/25

6:00 am-11:56 am

1 stop6h 56m

San José Juan Santamaria Intl

Sat 5/2

1:21 pm-10:28 pm

1 stop8h 07m

$442

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 4/29

8:51 am-7:37 pm

1 stop11h 46m

San José Juan Santamaria Intl

Tue 6/30

11:13 am-9:36 pm

1 stop9h 23m

$442

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 5/6

12:15 pm-7:00 pm

1 stop7h 45m

San José Juan Santamaria Intl

Mon 5/11

1:10 pm-9:55 pm

1 stop7h 45m

$444

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 5/4

7:30 am-7:00 pm

2 stops12h 30m

San José Juan Santamaria Intl

Mon 5/11

9:00 am-8:15 pm

2 stops10h 15m

$448

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 5/16

7:36 am-11:55 am

Nonstop5h 19m

San José Juan Santamaria Intl

Sat 5/23

12:30 am-12:44 pm

1 stop11h 14m

$463

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 3/26

3:22 pm-7:25 am

1 stop17h 03m

San José Juan Santamaria Intl

Thu 4/2

2:20 pm-1:13 am

1 stop9h 53m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 6/30

2:05 pm-10:39 pm

1 stop9h 34m

San José Juan Santamaria Intl

Sat 7/4

12:30 am-11:01 am

1 stop9h 31m

$479

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/28

Showing 1-10 of 40 resultsSorted by cheapest first
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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
OvagoPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-San José 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 flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-San José flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-San José 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 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?

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 20, 2026.

The price you pay for your flight from Chicago to San José may vary depending on when you book. For the best chance of a lower fare, look to book 14 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 Chicago to San José?

Currently, May is the cheapest month in which you can book a flight from Chicago to San José (average of $228). Flying from Chicago to San José in December is currently the most expensive (average of $343). 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 28, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to San José as you normally would.

Weekly flight availability from Chicago to San José

Explore weekly flight availability from Chicago to San José. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 28, 2026.

The most flights from CHI to SJO are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

How much does it cost to fly round-trip from Chicago to San José?

What’s the top layover airport for flights from Chicago to San José?

Share of 1-stop round-trip flights from Chicago to San José chosen by Cheapflights users in the past 12 months, using the same layover each way.

Panama City (PTY) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago to San José on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to San José?

Average round-trip fare for 1-stop flights from Chicago to San José, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Fort Lauderdale (FLL) is the most affordable 1-stop option, with an average round-trip price of $371.

What’s the fastest layover option from Chicago to San José?

Shortest average travel time for 1-stop one-way flights from Chicago to San José, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Fort Lauderdale (FLL) have the shortest average one-way travel time for 1-stop routes: 7h 06m.

Which airport typically offers the quickest layover for flights from Chicago to San José?

Average layover duration for 1-stop one-way flights from Chicago to San José, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Panama City (PTY) offer the fastest connection on this route, with an average layover time of 1h 29m.

How often are flights from Chicago to San José delayed?

About 20% of weekly flights between Chicago and San José have experienced delays in the past year, with the average delay time being 175 minutes.

What is the most punctual flight time for Chicago to San José flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Wednesday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to San José flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 14% of flights being delayed.

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 28, 2026.
Read through reviews of airlines operating flights from Chicago to San José, such as Copa Airlines, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.5
Good
1,557 reviews

Entertainment

6.8

Boarding

7.8

Food

6.8

Crew

8.1

Comfort

7.4

Overall

7.5

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
Copa Airlines
7.5
Good
1,557 reviews
Copa Airlines
7.5
Good
1,557 reviews

Entertainment

6.8

Boarding

7.8

Food

6.8

Crew

8.1

Comfort

7.4

Overall

7.5

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
United Airlines
7.4
Good
9,362 reviews
Copa Airlines
7.5
Good
1,557 reviews

Entertainment

6.8

Boarding

7.8

Food

6.8

Crew

8.1

Comfort

7.4

Overall

7.5

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
American Airlines
7.2
Good
11,367 reviews
Copa Airlines
7.5
Good
1,557 reviews

Entertainment

6.8

Boarding

7.8

Food

6.8

Crew

8.1

Comfort

7.4

Overall

7.5

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
Avianca
6.5
Okay
2,495 reviews
Copa Airlines
7.5
Good
1,557 reviews

Entertainment

6.8

Boarding

7.8

Food

6.8

Crew

8.1

Comfort

7.4

Overall

7.5

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
Spirit Airlines
6.3
Okay
8,492 reviews
Copa Airlines
7.5
Good
1,557 reviews

Entertainment

6.8

Boarding

7.8

Food

6.8

Crew

8.1

Comfort

7.4

Overall

7.5

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.

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 is 1 daily inbound flight from Chicago from 8 different airlines.

  • How long is the flight from Chicago to San José?

    A quick flight from Chicago to San José can take about 6h 56m. Spirit Airlines provides one of the quickest options available for as low as $442. Airlines will cover a distance of 2206 mi. This flight may include one or multiple stops.

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

    Cheapflights users have booked flights from Chicago to San José round-trip from $148. Other airlines that can offer you cheap pricing are Delta, from $205, and Spirit Airlines, from $227. Avianca is currently priced 70% below the average price you’ll pay for this route.

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

    The cheapest airlines for a one-way flight from Chicago to San José are Spirit Airlines ($88), Frontier ($136), and Delta ($136).

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

    The cheapest flight price from Chicago to San José is $211. On average you can expect to pay $431. The most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), can usually be booked for $312.

  • 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?

    Currently, May is the cheapest month in which you can book a flight from Chicago to San José (average of $228). Flying from Chicago to San José in December is currently the most expensive (average of $343). 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 San José?

Book flights to San José if you plan to visit one of these locations
Alajuela
Monteverde
Jacó
Heredia
Dominical
Manuel Antonio

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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 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
AviancaCheapest$148Average$386FlexibilityNo cancel feeOn-time71%
DeltaCheapest$205Average$483FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$227Average$375FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$256Average$466FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$340Average$553FlexibilityNo cancel feeOn-time71%
FrontierCheapest$345Average$796FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$385Average$591FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$394Average$592FlexibilityNo cancel feeOn-time63%

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