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San José

$90+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Feb 1 — Feb 81
Sun 2/1
Sun 2/8
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

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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 15 days in advance, depart on a Tuesday or Thursday 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 January 2, 2026.

This American Airlines deal was found by Cheapflights users on 12/31. 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.
Wed 12/313:10 pmORD - SJO
Nonstop5h 04mAmerican Airlines
Fri 1/96:00 amSJO - ORD
1 stop12h 10mAmerican Airlines
Deal found 12/31$472
This American Airlines deal was found by Cheapflights users on 12/31. 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.
Wed 12/313:10 pmORD - SJO
Nonstop5h 04mAmerican Airlines
Thu 1/86:00 amSJO - ORD
1 stop10h 20mAmerican Airlines
Deal found 12/31$497
This Avianca deal was found by Cheapflights users on 12/31. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:35 pmORD - SJO
1 stop7h 15mAvianca
Wed 1/77:50 pmSJO - ORD
1 stop19h 00mAvianca
Deal found 12/31$581
This American Airlines deal was found by Cheapflights users on 12/31. 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.
Wed 12/313:10 pmORD - SJO
Nonstop5h 04mAmerican Airlines
Wed 1/77:09 amSJO - ORD
Nonstop5h 29mAmerican Airlines
Deal found 12/31$588
This United Airlines deal was found by Cheapflights users on 12/31. 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.
Wed 12/317:39 amORD - SJO
Nonstop5h 17mUnited Airlines
Tue 1/66:30 amSJO - ORD
1 stop25h 17mUnited Airlines
Deal found 12/31$613
This Delta deal was found by Cheapflights users on 12/31. 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 12/316:08 pmMDW - SJO
2 stops18h 48mDelta
Mon 1/57:00 amSJO - MDW
1 stop9h 29mDelta
Deal found 12/31$930
This Delta deal was found by Cheapflights users on 12/31. 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 12/316:00 amMDW - SJO
1 stop6h 56mDelta
Wed 1/72:31 pmSJO - MDW
1 stop7h 36mDelta
Deal found 12/31$1,578
This Delta deal was found by Cheapflights users on 12/31. 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 12/319:50 amMDW - SJO
1 stop12h 05mDelta
Tue 1/67:00 amSJO - MDW
1 stop15h 07mDelta
Deal found 12/31$1,731

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 January 2, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$344
(Kiwi.com)

One-way from

$90
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$523

Good round-trip deal

$445 or less

Good one-way deal

$258 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
Search Deals
One-way flight from Chicago (CHI) to San José Juan Santamaria Intl
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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.
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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 January 2, 2026.
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

Sat 2/7

2:22 pm-7:06 am

1 stop16h 44m

San José Juan Santamaria Intl

Sun 2/15

2:54 pm-12:04 am

1 stop9h 10m

$346

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 2/9

2:22 pm-8:21 am

1 stop17h 59m

San José Juan Santamaria Intl

Sun 2/15

10:08 am-12:04 am

1 stop13h 56m

$347

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 2/15

2:22 pm-8:21 am

1 stop17h 59m

San José Juan Santamaria Intl

Sun 2/22

5:51 pm-12:31 pm

1 stop18h 40m

$347

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 2/10

7:34 am-4:48 pm

1 stop9h 14m

San José Juan Santamaria Intl

Tue 2/17

8:11 am-12:04 am

1 stop15h 53m

$347

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 1/25

2:13 pm-7:06 am

1 stop16h 53m

San José Juan Santamaria Intl

Sun 2/1

5:50 am-12:04 am

1 stop18h 14m

$347

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 1/29

8:54 am-8:39 pm

1 stop11h 45m

San José Juan Santamaria Intl

Thu 2/5

2:05 pm-7:35 pm

Nonstop5h 30m

$374

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 2/21

6:00 am-10:02 pm

1 stop16h 02m

San José Juan Santamaria Intl

Tue 2/24

7:00 am-10:33 pm

1 stop15h 33m

$385

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 2/3

7:50 pm-1:15 pm

1 stop17h 25m

San José Juan Santamaria Intl

Fri 2/6

2:05 pm-7:35 pm

Nonstop5h 30m

$388

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 2/22

6:05 am-12:50 pm

1 stop6h 45m

San José Juan Santamaria Intl

Fri 2/27

9:40 am-8:55 pm

2 stops11h 15m

$389

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 2/5

9:33 am-1:00 pm

2 stops27h 27m

San José Juan Santamaria Intl

Wed 2/11

2:31 pm-12:46 pm

2 stops22h 15m

$389

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/1

Showing 1-10 of 43 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
OvagoPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-San José flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 December 26, 2025.

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 15 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, October is the cheapest month in which you can book a flight from Chicago to San José (average of $248). Flying from Chicago to San José in March is currently the most expensive (average of $380). 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 January 2, 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.

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 10% of weekly flights between Chicago and San José have experienced delays in the past year, with the average delay time being 173 minutes.

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

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

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

Monday 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 10% 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 January 2, 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
7.6
Good
1,566 reviews

Overall

7.6

Crew

8.1

Comfort

7.4

Food

6.8

Entertainment

6.8

Boarding

7.8

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
7.6
Good
1,566 reviews
Copa Airlines
7.6
Good
1,566 reviews

Overall

7.6

Crew

8.1

Comfort

7.4

Food

6.8

Entertainment

6.8

Boarding

7.8

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
9,128 reviews
Copa Airlines
7.6
Good
1,566 reviews

Overall

7.6

Crew

8.1

Comfort

7.4

Food

6.8

Entertainment

6.8

Boarding

7.8

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
11,075 reviews
Copa Airlines
7.6
Good
1,566 reviews

Overall

7.6

Crew

8.1

Comfort

7.4

Food

6.8

Entertainment

6.8

Boarding

7.8

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
6.6
Okay
2,495 reviews
Copa Airlines
7.6
Good
1,566 reviews

Overall

7.6

Crew

8.1

Comfort

7.4

Food

6.8

Entertainment

6.8

Boarding

7.8

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
8,257 reviews
Copa Airlines
7.6
Good
1,566 reviews

Overall

7.6

Crew

8.1

Comfort

7.4

Food

6.8

Entertainment

6.8

Boarding

7.8

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 are 2 daily inbound flights 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 45m. Copa Airlines provides one of the quickest options available for as low as $389. 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 $206. Other airlines that can offer you cheap pricing are Spirit Airlines, from $255, and Copa Airlines, from $256. Delta is currently priced 60% 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 ($96), Delta ($136), and American Airlines ($150).

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

    The cheapest flight price from Chicago to San José is $158. On average you can expect to pay $862. The most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), can usually be booked for $225.

  • 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, October is the cheapest month in which you can book a flight from Chicago to San José (average of $248). Flying from Chicago to San José in March is currently the most expensive (average of $380). 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
Manuel Antonio
Alajuela
Monteverde
Jacó
Heredia
Dominical

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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 January 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$221Average$645FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$257Average$381FlexibilityNo cancel feeOn-time65%
AviancaCheapest$307Average$454FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$309Average$507FlexibilityNo cancel feeOn-time70%
FrontierCheapest$345Average$796FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$349Average$590FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$394Average$599FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$423Average$642FlexibilityNo cancel feeOn-time69%

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