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$96+ Cheap flights from Illinois 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJO
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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Cheap flight deals from Illinois to Costa Rica

Keep the following information in mind while searching for Illinois to Costa Rica flight deals. Data was last updated November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$293
(KAYAK)

One-way from

$96
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$508

Good round-trip deal

$461 or less

Good one-way deal

$176 or less
Provider with most accurate pricing for Chicago (CHI)-San José Juan Santamaria Intl flight deals.
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From Illinois to Costa Rica
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One-way flight from Illinois to Costa Rica
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Highest demand for flights based on searches. 10% potential increase in price ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Illinois to Costa Rica.
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Price to beat on a one-way flight from Illinois to Costa Rica.
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Find flight deals from Illinois to Costa Rica

Cheapest flights from Illinois to Costa Rica
Explore the most affordable flight options available from Illinois to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/23. 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 12/313:26 pmORD - SJO
1 stop20h 59mSpirit Airlines
Thu 1/151:30 pmSJO - ORD
1 stop10h 16mSpirit Airlines
Deal found 11/23$300
This Cheapflightsfares deal was found by Cheapflights users on 11/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/24:58 pmORD - SJO
1 stop17h 21mSpirit Airlines
Wed 12/101:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/24$301
This Mytrip deal was found by Cheapflights users on 11/25. 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 12/84:38 pmORD - SJO
2 stops22h 42mMultiple Airlines
Sat 12/131:31 pmSJO - ORD
1 stop10h 38mMultiple Airlines
Deal found 11/25$306
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com 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
Thu 12/111:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/24$307
This CheapOair deal was found by Cheapflights users on 11/24. 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.
Sat 12/65:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Tue 12/912:39 pmSJO - ORD
2 stops11h 30mSpirit Airlines
Deal found 11/24$308
This Kiwi.com deal was found by Cheapflights users on 11/23. 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 12/313:26 pmORD - SJO
2 stops20h 16mMultiple Airlines
Wed 1/141:30 pmSJO - ORD
1 stop31h 27mMultiple Airlines
Deal found 11/23$309
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/24:58 pmORD - SJO
1 stop17h 21mSpirit Airlines
Thu 12/111:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/24$310
This Mytrip deal was found by Cheapflights users on 11/25. 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 12/84:38 pmORD - SJO
2 stops19h 04mSpirit Airlines
Sat 12/131:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/25$311
This Mytrip deal was found by Cheapflights users on 11/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/147:20 amORD - SJO
1 stop8h 00mMultiple Airlines
Mon 12/221:31 pmSJO - ORD
1 stop10h 59mMultiple Airlines
Deal found 11/24$315
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/88:36 amORD - SJO
2 stops27h 06mMultiple Airlines
Thu 12/181:31 pmSJO - ORD
1 stop10h 59mMultiple Airlines
Deal found 11/24$316
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/15:47 pmMDW - SJO
1 stop16h 32mMultiple Airlines
Tue 12/161:31 pmSJO - MDW
2 stops19h 15mMultiple Airlines
Deal found 11/24$346
This Air Canada deal was found by Cheapflights users on 11/25. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/104:05 pmSTL - LIR
1 stop22h 40mAir Canada
Sun 12/143:45 pmLIR - STL
1 stop23h 44mAir Canada
Deal found 11/25$351

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois 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 November 26, 2025.
Use the filters below to find and compare flights from Illinois to Costa Rica that are best for you.

Fly from

Illinois

Fly to

Costa Rica

Route

Depart

Return

Price

St. LouisLiberia

STL - LIR

STLLIR

Lambert-St Louis

Tue 1/20

6:00 am-1:10 pm

1 stop7h 10m

Liberia

Tue 1/27

8:35 am-3:52 pm

1 stop7h 17m

$331

St. LouisLiberia

STL - LIR

STLLIR

Lambert-St Louis

Tue 1/20

7:10 am-1:50 pm

1 stop6h 40m

Liberia

Wed 1/28

2:45 pm-11:25 pm

1 stop8h 40m

$331

St. LouisLiberia

STL - LIR

STLLIR

Lambert-St Louis

Mon 2/2

6:00 am-6:37 pm

1 stop12h 37m

Liberia

Fri 2/13

8:35 am-10:14 pm

1 stop13h 39m

$331

St. LouisLiberia

STL - LIR

STLLIR

Lambert-St Louis

Sun 1/18

6:00 am-1:50 pm

1 stop7h 50m

Liberia

Thu 1/22

3:05 pm-8:53 am

1 stop17h 48m

$331

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 2/20

2:22 pm-7:06 am

1 stop16h 44m

San José Juan Santamaria Intl

Fri 2/27

11:01 am-12:04 am

1 stop13h 03m

$345

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 2/5

2:22 pm-7:06 am

1 stop16h 44m

San José Juan Santamaria Intl

Sun 2/15

10:08 am-12:04 am

1 stop13h 56m

$345

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 2/18

7:34 am-6:56 pm

1 stop11h 22m

San José Juan Santamaria Intl

Tue 2/24

4:09 am-12:31 pm

1 stop8h 22m

$345

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 2/19

2:22 pm-8:21 am

1 stop17h 59m

San José Juan Santamaria Intl

Mon 2/23

10:08 am-12:04 am

1 stop13h 56m

$345

St. LouisSan José

STL - SJO

STLSJO

Lambert-St Louis

Sun 1/25

7:10 am-10:15 pm

1 stop15h 05m

San José Juan Santamaria Intl

Wed 1/28

2:31 pm-11:37 pm

1 stop9h 06m

$352

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 2/14

2:22 pm-8:21 am

1 stop17h 59m

San José Juan Santamaria Intl

Thu 2/19

4:09 am-12:31 pm

1 stop8h 22m

$360

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 60 results
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Best time to book a flight from Illinois to Costa Rica

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

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

Currently, October is the cheapest month in which you can book a flight from Illinois to Costa Rica (average of $248). Flying from Illinois to Costa Rica 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 IL to CR?

Find hourly flight availability from Illinois 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 November 26, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 28% on flights from Illinois to Costa Rica by exploring options for tickets in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Illinois to Costa Rica. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Illinois to Costa Rica 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.

Related info for your journey

Find useful and relevant information for your journey from Illinois to Costa Rica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Illinois to Costa Rica?

    Airlines like United Airlines, Delta, and Copa Airlines fly from Illinois to Costa Rica in about 6h 40m. The time it takes to get you to your destination can typically vary by up to 10h 04m. Airlines will cover a distance of 1967 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Illinois to Costa Rica one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $134. Users have also found prices from $138 and $143 on Delta and American Airlines, respectively.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Illinois to Costa Rica (average of $248). Flying from Illinois to Costa Rica 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

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Alternative routes for Illinois to Costa Rica

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Illinois to Costa Rica

Discover the top 8 airlines that operate flights from Illinois 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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$221Average$680FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$258Average$396FlexibilityNo cancel feeOn-time65%
AviancaCheapest$307Average$463FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$309Average$512FlexibilityNo cancel feeOn-time70%
FrontierCheapest$345Average$796FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$347Average$683FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$394Average$645FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$430Average$716FlexibilityNo cancel feeOn-time69%

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