Costa Rica

$142+ Cheap flights from Chicago (CHI) to Costa Rica

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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
abr. 27 — may. 41
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Cheap flight deals from Chicago to Costa Rica

Keep the following information in mind while searching for Chicago to Costa Rica flight deals. Data was last updated abril 22, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$332
(Cheapflightsfares)

One-way from

$142
(Mytrip)

Popular in

December

Cheapest in

May

Average price

$646

Good round-trip deal

$550 or less

Good one-way deal

$245 or less
Provider with most accurate pricing for Chicago (CHI)-San José Juan Santamaria Intl flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-San José Juan Santamaria Intl flights.
From Chicago (CHI) to Costa Rica
One-way flight from Chicago (CHI) to Costa Rica
Highest demand for flights based on searches. 10% potential increase in price ($74 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Average for round-trip flights in April 2025
Price to beat on a round-trip flight from Chicago (CHI) to Costa Rica.
Price to beat on a one-way flight from Chicago (CHI) to Costa Rica.

Find flight deals from Chicago to Costa Rica

Cheapest flights from Chicago to Costa Rica
Explore the most affordable flight options available from Chicago to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 22, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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.
vie. 5/97:35 pmORD - SJO
1 stop16h 58mSpirit Airlines
mar. 5/1312:28 pmSJO - ORD
1 stop9h 36mSpirit Airlines
Deal found 4/22$328
This CheapOair deal was found by Cheapflights users on 4/21. 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.
jue. 6/57:35 pmORD - SJO
1 stop16h 58mMultiple Airlines
lun. 6/92:48 pmSJO - ORD
1 stop13h 54mMultiple Airlines
Deal found 4/21$334
This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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.
mié. 6/43:45 pmORD - SJO
2 stops17h 55mAvianca
sáb. 6/75:05 amSJO - ORD
1 stop10h 00mAvianca
Deal found 4/22$367
This Copa Airlines deal was found by Cheapflights users on 4/22. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/46:56 amORD - SJO
1 stop12h 00mCopa Airlines
mar. 11/114:13 amSJO - ORD
1 stop8h 09mCopa Airlines
Deal found 4/22$387
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
lun. 6/29:12 pmMDW - SJO
1 stop14h 15mMultiple Airlines
lun. 6/95:52 amSJO - MDW
2 stops12h 39mMultiple Airlines
Deal found 4/22$420
This United Airlines deal was found by Cheapflights users on 4/21. 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.
sáb. 5/177:35 amORD - SJO
1 stop13h 02mUnited Airlines
sáb. 5/241:00 pmSJO - ORD
Nonstop5h 34mUnited Airlines
Deal found 4/21$432
This Southwest deal was found by Cheapflights users on 4/22. 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.
vie. 9/55:05 amMDW - SJO
1 stop8h 40mSouthwest
vie. 9/191:40 pmSJO - MDW
1 stop9h 25mSouthwest
Deal found 4/22$437
This Delta deal was found by Cheapflights users on 4/22. 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.
sáb. 4/265:30 amORD - SJO
1 stop8h 58mDelta
sáb. 5/32:53 pmSJO - ORD
1 stop8h 06mDelta
Deal found 4/22$443
This Delta deal was found by Cheapflights users on 4/21. 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.
mié. 9/36:00 amMDW - SJO
1 stop6h 48mDelta
lun. 9/81:18 pmSJO - MDW
1 stop7h 26mDelta
Deal found 4/21$446
This American Airlines deal was found by Cheapflights users on 4/22. 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.
mar. 4/226:00 amORD - SJO
1 stop17h 04mAmerican Airlines
dom. 4/276:05 amSJO - ORD
1 stop16h 49mAmerican Airlines
Deal found 4/22$448
This Southwest deal was found by Cheapflights users on 4/20. 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.
jue. 7/249:45 pmMDW - LIR
2 stops16h 25mSouthwest
lun. 7/282:10 pmLIR - MDW
1 stop7h 40mSouthwest
Deal found 4/20$580
This Delta deal was found by Cheapflights users on 4/22. 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.
vie. 8/226:00 amORD - LIR
1 stop7h 00mDelta
mar. 8/261:25 pmLIR - ORD
1 stop9h 30mDelta
Deal found 4/22$584

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Costa Rica 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 abril 22, 2025.
Use the filters below to find and compare flights from Chicago to Costa Rica that are best for you.

Fly from

Chicago

Fly to

Costa Rica

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

vie. 5/9

7:35 pm-11:33 am

1 stop16h 58m

San José Juan Santamaria Intl

mar. 5/13

12:28 pm-11:04 pm

1 stop9h 36m

$328

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

jue. 6/5

7:35 pm-11:33 am

1 stop16h 58m

San José Juan Santamaria Intl

lun. 6/9

2:48 pm-5:42 am

1 stop13h 54m

$334

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

mié. 6/4

3:45 pm-8:40 am

2 stops17h 55m

San José Juan Santamaria Intl

sáb. 6/7

5:05 am-4:05 pm

1 stop10h 00m

$367

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

jue. 7/3

3:07 pm-7:35 am

1 stop17h 28m

San José Juan Santamaria Intl

dom. 7/6

8:09 am-11:52 pm

1 stop14h 43m

$410

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

lun. 6/2

9:12 pm-10:27 am

1 stop14h 15m

San José Juan Santamaria Intl

lun. 6/9

5:52 am-7:31 pm

2 stops12h 39m

$420

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

sáb. 5/17

7:35 am-7:37 pm

1 stop13h 02m

San José Juan Santamaria Intl

sáb. 5/24

1:00 pm-7:34 pm

Nonstop5h 34m

$432

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

sáb. 4/26

5:30 am-1:28 pm

1 stop8h 58m

San José Juan Santamaria Intl

sáb. 5/3

2:53 pm-11:59 pm

1 stop8h 06m

$443

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

dom. 4/27

8:27 am-6:24 pm

2 stops10h 57m

San José Juan Santamaria Intl

sáb. 5/3

6:05 am-7:29 pm

2 stops12h 24m

$448

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mar. 6/3

5:55 am-12:10 pm

1 stop7h 15m

San José Juan Santamaria Intl

lun. 6/9

8:45 am-9:25 pm

2 stops11h 40m

$490

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

sáb. 4/26

6:04 am-1:28 pm

1 stop8h 24m

San José Juan Santamaria Intl

sáb. 5/3

1:20 pm-10:22 pm

1 stop8h 02m

$507

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 43 results
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Best time to book a flight from Chicago to Costa Rica

Have a flexible travel schedule? Discover the best time to fly to Costa Rica 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 Costa Rica

What is the cheapest month to book a flight from Chicago to Costa Rica?

Currently, September is the cheapest month in which you can book a flight from Chicago to Costa Rica (average of $398). Flying from Chicago to Costa Rica in March is currently the most expensive (average of $555). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to CR?

Find hourly flight availability from Chicago to Costa Rica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated abril 22, 2025.

When flying from Chicago to Costa Rica, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 46% versus a flight at noon.

What is the cheapest day to fly from Chicago to Costa Rica?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Costa Rica. Price data was last updated on April 7, 2024.

Travelers seeking maximum savings on their Chicago to Costa Rica flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Costa Rica by month

Plan your trip to Costa Rica by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Costa Rica ranges from 0.0 - 11.8 inches per month. September is typically the wettest month, when rainfall can reach 11.8 in. February is typically the driest time to visit Costa Rica when rainfall is around 0.0 in.

Temperature in Costa Rica by month

Plan your trip to Costa Rica by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Costa Rica, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 64.4 F).

Reviews of airlines servicing Costa Rica

Get insights into the airlines that provide service to Costa Rica. 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 Costa Rica. Reviews last updated abril 22, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from Chicago to Costa Rica by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
8.0
Very good

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Related info for your journey

Find useful and relevant information for your journey from Chicago to Costa Rica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • What are the cheapest airlines to fly from Chicago to Costa Rica one-way?

    The cheapest airlines for a one-way flight from Chicago to Costa Rica are Spirit Airlines ($142), Frontier ($171), and Delta ($205).

  • What are the most popular routes from Chicago to Costa Rica?

  • What are the cheapest flights from Chicago to Costa Rica?

    While on average a flight from Chicago to Costa Rica is generally $536, our data shows the cheapest flight currently is $200. When looking at the most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), you can expect to pay $285 for that flight.

  • Can I find deals for flights from Chicago to Costa Rica that include hotel bookings?

    Yes. In addition to deals on Chicago to Costa Rica flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Costa Rica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Costa Rica.

  • Can I find deals for business class flights from Chicago to Costa Rica?

    Yes. Cheapflights offers flight deals from Chicago to Costa Rica 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 Costa Rica?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Costa Rica (average of $398). Flying from Chicago to Costa Rica in March is currently the most expensive (average of $555). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top 8 airlines flying from Chicago to Costa Rica

Discover the top 8 airlines that operate flights from Chicago to Costa Rica. 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 abril 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$245Average$416FlexibilityNo cancel feeOn-time65%
AviancaCheapest$337Average$489FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$345Average$635FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$416Average$616FlexibilityNo cancel feeOn-time70%
DeltaCheapest$442Average$795FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$480Average$738FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$540Average$667FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$548Average$838FlexibilityNo cancel feeOn-time69%

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