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San José

$106+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Jan 4 — Jan 111
Sun 1/4
Sun 1/11
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

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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 Friday

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 December 5, 2025.

This Expedia deal was found by Cheapflights users on 12/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Thu 12/181:31 pmSJO - ORD
1 stop10h 59mSpirit Airlines
Deal found 12/2$341
This American Airlines deal was found by Cheapflights users on 12/5. 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.
Mon 12/85:18 pmORD - SJO
Nonstop5h 10mAmerican Airlines
Wed 12/106:00 amSJO - ORD
Nonstop5h 31mAmerican Airlines
Deal found 12/5$343
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/312:35 pmORD - SJO
1 stop7h 15mMultiple Airlines
Fri 1/92:58 pmSJO - ORD
1 stop20h 37mMultiple Airlines
Deal found 12/3$348
This Mytrip deal was found by Cheapflights users on 12/3. 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 12/66:11 amORD - SJO
1 stop7h 41mMultiple Airlines
Sun 12/141:31 pmSJO - ORD
1 stop10h 38mMultiple Airlines
Deal found 12/3$353
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/64:10 pmORD - SJO
1 stop16h 30mMultiple Airlines
Wed 12/101:31 pmSJO - ORD
1 stop24h 26mMultiple Airlines
Deal found 12/3$354
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/108:00 amORD - SJO
2 stops27h 42mMultiple Airlines
Thu 12/181:31 pmSJO - ORD
1 stop10h 59mMultiple Airlines
Deal found 12/2$356
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/312:35 pmORD - SJO
1 stop7h 15mMultiple Airlines
Sun 1/117:45 amSJO - ORD
1 stop24h 33mMultiple Airlines
Deal found 12/3$360
This Cheapflightsfares deal was found by Cheapflights users on 12/3. 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.
Sun 12/75:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Sun 12/141:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 12/3$363
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/104:38 pmORD - SJO
2 stops23h 32mMultiple Airlines
Mon 12/151:31 pmSJO - ORD
1 stop21h 37mMultiple Airlines
Deal found 12/3$371
This Southwest deal was found by Cheapflights users on 12/3. 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 12/1010:15 amMDW - SJO
1 stop10h 15mSouthwest
Tue 12/169:00 amSJO - MDW
1 stop7h 35mSouthwest
Deal found 12/3$411
This Southwest deal was found by Cheapflights users on 12/2. 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 12/1010:15 amMDW - SJO
1 stop10h 15mSouthwest
Thu 12/189:00 amSJO - MDW
1 stop8h 05mSouthwest
Deal found 12/2$426
This Gurufare deal was found by Cheapflights users on 12/3. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:12 amMDW - SJO
1 stop7h 30mFrontier
Wed 1/73:10 pmSJO - MDW
1 stop20h 21mFrontier
Deal found 12/3$437

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 December 5, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$317
(Kiwi.com)

One-way from

$106
(Super.com)

Popular in

December

Cheapest in

September

Average price

$671

Good round-trip deal

$463 or less

Good one-way deal

$176 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 December 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 December 5, 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

Sat 2/21

6:33 pm-3:30 pm

1 stop20h 57m

San José Juan Santamaria Intl

Sat 2/28

7:45 am-6:15 pm

1 stop10h 30m

$336

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 3/5

2:22 pm-8:20 am

1 stop17h 58m

San José Juan Santamaria Intl

Wed 3/11

4:09 am-1:31 pm

1 stop8h 22m

$345

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 2/1

7:35 am-8:39 pm

1 stop13h 04m

San José Juan Santamaria Intl

Fri 2/6

2:05 pm-7:35 pm

Nonstop5h 30m

$347

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 1/15

6:57 pm-3:30 pm

1 stop20h 33m

San José Juan Santamaria Intl

Mon 1/19

7:45 am-8:18 am

1 stop24h 33m

$355

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 2/22

5:25 am-10:02 pm

1 stop16h 37m

San José Juan Santamaria Intl

Fri 3/6

7:00 am-8:57 pm

1 stop13h 57m

$357

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 3/6

2:22 pm-8:20 am

1 stop17h 58m

San José Juan Santamaria Intl

Fri 3/13

4:09 am-1:31 pm

1 stop8h 22m

$360

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 1/25

6:50 am-10:15 pm

2 stops15h 25m

San José Juan Santamaria Intl

Tue 2/3

2:31 pm-1:13 pm

2 stops22h 42m

$361

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 2/16

10:53 am-10:02 pm

1 stop11h 09m

San José Juan Santamaria Intl

Mon 2/23

7:00 am-5:45 pm

1 stop10h 45m

$384

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 2/4

2:22 pm-7:06 am

1 stop16h 44m

San José Juan Santamaria Intl

Mon 2/9

8:48 am-12:04 am

1 stop15h 16m

$385

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 3/4

5:45 am-1:15 pm

1 stop7h 30m

San José Juan Santamaria Intl

Sat 3/7

2:05 pm-7:35 pm

Nonstop5h 30m

$387

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Showing 1-10 of 42 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 December.
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 November 28, 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 $367). 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 December 5, 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 61% 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.

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 December 5, 2025.

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

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 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, 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 December 5, 2025.
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
1,554 reviews

Crew

8.1

Overall

7.6

Boarding

7.8

Comfort

7.4

Entertainment

6.8

Food

6.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

PEI - PTY

The attention to us was excellent. Help was provided with care.
Copa Airlines
7.6
Good
1,554 reviews
Copa Airlines
7.6
Good
1,554 reviews

Crew

8.1

Overall

7.6

Boarding

7.8

Comfort

7.4

Entertainment

6.8

Food

6.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

PEI - PTY

The attention to us was excellent. Help was provided with care.
United Airlines
7.4
Good
9,063 reviews
Copa Airlines
7.6
Good
1,554 reviews

Crew

8.1

Overall

7.6

Boarding

7.8

Comfort

7.4

Entertainment

6.8

Food

6.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

PEI - PTY

The attention to us was excellent. Help was provided with care.
American Airlines
7.2
Good
11,047 reviews
Copa Airlines
7.6
Good
1,554 reviews

Crew

8.1

Overall

7.6

Boarding

7.8

Comfort

7.4

Entertainment

6.8

Food

6.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

PEI - PTY

The attention to us was excellent. Help was provided with care.
Avianca
6.6
Okay
2,480 reviews
Copa Airlines
7.6
Good
1,554 reviews

Crew

8.1

Overall

7.6

Boarding

7.8

Comfort

7.4

Entertainment

6.8

Food

6.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

PEI - PTY

The attention to us was excellent. Help was provided with care.
Spirit Airlines
6.3
Okay
8,156 reviews
Copa Airlines
7.6
Good
1,554 reviews

Crew

8.1

Overall

7.6

Boarding

7.8

Comfort

7.4

Entertainment

6.8

Food

6.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

PEI - PTY

The attention to us was excellent. Help was provided with care.

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 13h 04m. Copa Airlines provides one of the quickest options available for as low as $347. 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 $206. Other airlines that can offer you cheap pricing are Copa Airlines, from $256, and Spirit Airlines, from $257. Delta is currently priced 61% 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 $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 $242.

  • 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 $25 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 $367). 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 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 December 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$221Average$652FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$259Average$391FlexibilityNo cancel feeOn-time65%
AviancaCheapest$307Average$462FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$309Average$511FlexibilityNo cancel feeOn-time70%
FrontierCheapest$345Average$796FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$347Average$614FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$394Average$598FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$442Average$668FlexibilityNo cancel feeOn-time69%

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