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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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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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 Wednesday and return on a Friday

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 November 20, 2025.

This Mytrip deal was found by Cheapflights users on 11/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:00 amORD - SJO
1 stop7h 25mMultiple Airlines
Sat 12/138:07 amSJO - ORD
2 stops14h 04mMultiple Airlines
Deal found 11/19$287
This Kiwi.com deal was found by Cheapflights users on 11/18. 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.
Thu 12/116:15 amORD - SJO
2 stops29h 27mMultiple Airlines
Mon 12/151:31 pmSJO - ORD
1 stop21h 37mMultiple Airlines
Deal found 11/18$290
This KAYAK deal was found by Cheapflights users on 11/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:26 pmORD - SJO
1 stop20h 59mSpirit Airlines
Mon 12/151:31 pmSJO - ORD
1 stop21h 37mSpirit Airlines
Deal found 11/19$291
This Cheapflightsfares deal was found by Cheapflights users on 11/19. 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.
Wed 12/35:00 amORD - SJO
1 stop7h 15mSpirit Airlines
Wed 12/101:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/19$292
This Mytrip deal was found by Cheapflights users on 11/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/84:38 pmORD - SJO
2 stops22h 42mMultiple Airlines
Sat 12/138:07 amSJO - ORD
2 stops14h 04mMultiple Airlines
Deal found 11/19$294
This Kiwi.com deal was found by Cheapflights users on 11/18. 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.
Thu 11/276:23 pmORD - SJO
1 stop15h 56mMultiple Airlines
Wed 12/31:20 pmSJO - ORD
1 stop21h 48mMultiple Airlines
Deal found 11/18$295
This Mytrip deal was found by Cheapflights users on 11/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/103:26 pmORD - SJO
2 stops23h 54mMultiple Airlines
Tue 12/1612:39 pmSJO - ORD
2 stops22h 29mMultiple Airlines
Deal found 11/19$296
This KAYAK deal was found by Cheapflights users on 11/17. 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.
Mon 12/14:58 pmORD - SJO
1 stop17h 21mSpirit Airlines
Fri 12/121:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/17$297
This Kiwi.com deal was found by Cheapflights users on 11/17. 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.
Thu 12/116:15 amORD - SJO
1 stop30h 10mMultiple Airlines
Fri 12/191:31 pmSJO - ORD
1 stop10h 59mMultiple Airlines
Deal found 11/17$298
This KAYAK deal was found by Cheapflights users on 11/18. 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.
Wed 12/103:26 pmORD - SJO
2 stops20h 16mSpirit Airlines
Sat 12/131:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/18$299
This Mytrip deal was found by Cheapflights users on 11/18. 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.
Wed 12/103:26 pmORD - SJO
2 stops23h 54mMultiple Airlines
Wed 12/1712:39 pmSJO - ORD
2 stops22h 35mMultiple Airlines
Deal found 11/18$300
This Kiwi.com deal was found by Cheapflights users on 11/18. 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.
Fri 11/284:46 pmMDW - SJO
1 stop17h 33mMultiple Airlines
Sun 12/71:31 pmSJO - MDW
2 stops43h 15mMultiple Airlines
Deal found 11/18$322

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 November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$285
(Kiwi.com)

One-way from

$90
(Spirit)

Popular in

December

Cheapest in

September

Average price

$505

Good round-trip deal

$396 or less

Good one-way deal

$217 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. 10% potential increase in price ($61 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 20, 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

Tue 1/27

2:13 pm-9:52 pm

1 stop7h 39m

San José Juan Santamaria Intl

Tue 1/27

4:09 am-12:46 pm

1 stop8h 37m

$380

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 12/31

6:12 am-1:42 pm

1 stop7h 30m

San José Juan Santamaria Intl

Wed 1/7

3:10 pm-11:31 am

1 stop20h 21m

$383

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 2/6

2:22 pm-8:21 am

1 stop17h 59m

San José Juan Santamaria Intl

Mon 2/16

6:08 pm-12:31 pm

1 stop18h 23m

$384

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 11/29

2:07 pm-7:33 am

1 stop17h 26m

San José Juan Santamaria Intl

Tue 12/9

4:08 am-12:52 pm

1 stop8h 44m

$384

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 1/30

7:35 am-6:38 pm

1 stop11h 03m

San José Juan Santamaria Intl

Wed 2/4

4:09 am-12:31 pm

1 stop8h 22m

$388

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 1/19

7:39 am-12:56 pm

Nonstop5h 17m

San José Juan Santamaria Intl

Fri 1/23

2:05 pm-7:35 pm

Nonstop5h 30m

$395

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 12/11

2:07 pm-7:10 am

1 stop17h 03m

San José Juan Santamaria Intl

Sat 12/13

4:08 am-12:52 pm

1 stop8h 44m

$406

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 12/8

12:50 pm-10:20 pm

1 stop9h 30m

San José Juan Santamaria Intl

Sat 12/13

7:00 am-3:44 pm

1 stop8h 44m

$410

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 12/5

6:05 pm-6:25 am

1 stop12h 20m

San José Juan Santamaria Intl

Mon 12/8

11:28 pm-9:48 am

1 stop10h 20m

$410

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 1/26

12:48 pm-10:15 pm

1 stop9h 27m

San José Juan Santamaria Intl

Wed 1/28

2:31 pm-12:46 pm

2 stops22h 15m

$414

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 45 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 November.
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
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 November 14, 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 $364). 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 November 20, 2025.

One of the essential ways to save on airfare from Chicago to San José is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 62% on airfare.

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

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 flight should consider departing on Wednesday at noon when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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

How often are flights from Chicago to San José delayed?

About 11% of weekly flights between Chicago and San José have experienced delays in the past year, with the average delay time being 196 minutes.

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

Historically, flights departing in the evening 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, Qatar Airways have had the lowest number of delays on this route, with no flights being classified as 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 November 20, 2025.
Read through reviews of airlines operating flights from Chicago to San José, such as Southwest, Copa Airlines, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,249 reviews
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Copa Airlines
7.6
Good
1,566 reviews
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,029 reviews
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,045 reviews
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,154 reviews
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 9 different airlines.

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

    A quick flight from Chicago to San José can take about 5h 17m. Copa Airlines provides one of the quickest options available for as low as $395. Airlines will cover a distance of 2220 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 $221. Other airlines that can offer you cheap pricing are Spirit Airlines, from $259, and Avianca, from $307. Delta is currently priced 58% below the average price you’ll pay for this route.

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

    The cheapest flight price from Chicago to San José is $151. On average you can expect to pay $442. The most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), can usually be booked for $232.

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

    Chicago to San José flights have a layover in Fort Lauderdale most of the time.

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

    Fort Lauderdale travelers tend to visit Las Olas Beach, Port Everglades, and Fort Lauderdale Beach Park more than anywhere else. Las Olas Beach, Port Everglades, and Fort Lauderdale Beach Park can be visited by traveling about 4.1 mi, 2.1 mi, and 4.2 mi respectively from Fort Lauderdale. Those landing in Fort Lauderdale looking to spend some time exploring during their layover can rent a car for about $23 per day.

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

    Chicago to San José 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?

    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 $364). 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
Heredia
Manuel Antonio
Alajuela
Monteverde
Jacó
Dominical

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Top 9 airlines flying from Chicago to San José

Discover the top 9 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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$221Average$669FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$259Average$404FlexibilityNo cancel feeOn-time65%
AviancaCheapest$307Average$462FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$314Average$518FlexibilityNo cancel feeOn-time70%
FrontierCheapest$345Average$796FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$347Average$631FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$394Average$602FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$432Average$649FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$443Average$707FlexibilityNo cancel feeOn-time69%

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