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$123+ 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 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJO
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
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 January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$262
(Kiwi.com)

One-way from

$123
(Orbitz)

Popular in

December

Cheapest in

September

Average price

$521

Good round-trip deal

$457 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 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. 7% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 15, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/14. 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 2/163:49 pm
STL
-
SJO
1 stop19h 51m
Multiple Airlines
Tue 2/2412:35 pm
SJO
-
STL
1 stop9h 52m
Multiple Airlines
Deal found 1/14$262
This Kiwi.com deal was found by Cheapflights users on 1/13. 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 2/163:49 pm
STL
-
SJO
1 stop19h 51m
Multiple Airlines
Wed 2/2512:35 pm
SJO
-
STL
1 stop9h 52m
Multiple Airlines
Deal found 1/13$264
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 2/163:49 pm
STL
-
SJO
1 stop19h 51m
Multiple Airlines
Fri 2/2712:35 pm
SJO
-
STL
1 stop11h 52m
Multiple Airlines
Deal found 1/14$274
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
Sun 2/153:49 pm
STL
-
SJO
1 stop19h 51m
Multiple Airlines
Wed 2/2512:35 pm
SJO
-
STL
1 stop9h 52m
Multiple Airlines
Deal found 1/14$275
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
Sun 2/153:49 pm
STL
-
SJO
1 stop19h 51m
Multiple Airlines
Fri 2/2712:35 pm
SJO
-
STL
1 stop11h 52m
Multiple Airlines
Deal found 1/14$288
This Kiwi.com deal was found by Cheapflights users on 1/13. 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 2/163:49 pm
STL
-
SJO
1 stop19h 51m
Multiple Airlines
Thu 2/261:31 pm
SJO
-
STL
2 stops17h 20m
Multiple Airlines
Deal found 1/13$293
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 2/218:17 pm
STL
-
SJO
2 stops15h 23m
Multiple Airlines
Tue 2/2412:35 pm
SJO
-
STL
1 stop9h 52m
Multiple Airlines
Deal found 1/14$298
This United Airlines deal was found by Cheapflights users on 1/15. 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.
Sun 2/156:25 am
STL
-
LIR
2 stops12h 12m
United Airlines
Fri 2/208:35 am
LIR
-
STL
1 stop13h 39m
United Airlines
Deal found 1/15$342
This Copa Airlines deal was found by Cheapflights users on 1/13. 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.
Fri 2/202:22 pm
ORD
-
SJO
1 stop16h 44m
Copa Airlines
Sun 3/15:50 am
SJO
-
ORD
1 stop18h 14m
Copa Airlines
Deal found 1/13$346
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Sun 4/266:54 pm
STL
-
LIR
2 stops19h 16m
American Airlines
Fri 5/112:28 pm
LIR
-
STL
2 stops19h 29m
American Airlines
Deal found 1/14$347
This Kiwi.com deal was found by Cheapflights users on 1/13. 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 2/113:22 pm
ORD
-
SJO
2 stops20h 18m
Multiple Airlines
Thu 2/191:31 pm
SJO
-
ORD
1 stop7h 42m
Multiple Airlines
Deal found 1/13$347
This Gotogate deal was found by Cheapflights users on 1/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/204:43 pm
ORD
-
SJO
2 stops18h 57m
Multiple Airlines
Mon 2/232:50 pm
SJO
-
ORD
1 stop13h 46m
Multiple Airlines
Deal found 1/14$348

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 January 15, 2026.
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. LouisSan José

STL - SJO

STLSJO

Lambert-St Louis

Sun 2/15

3:49 pm-11:40 am

1 stop19h 51m

San José Juan Santamaria Intl

Tue 2/24

12:35 pm-10:27 pm

1 stop9h 52m

$275

St. LouisSan José

STL - SJO

STLSJO

Lambert-St Louis

Sat 2/21

8:17 pm-11:40 am

2 stops15h 23m

San José Juan Santamaria Intl

Wed 2/25

12:35 pm-10:27 pm

1 stop9h 52m

$293

St. LouisSan José

STL - SJO

STLSJO

Lambert-St Louis

Wed 2/18

3:49 pm-11:40 am

1 stop19h 51m

San José Juan Santamaria Intl

Sat 2/28

12:35 pm-11:59 pm

1 stop11h 24m

$332

St. LouisSan José

STL - SJO

STLSJO

Lambert-St Louis

Tue 2/17

3:49 pm-11:40 am

1 stop19h 51m

San José Juan Santamaria Intl

Thu 2/26

1:31 pm-6:51 am

2 stops17h 20m

$339

St. LouisLiberia

STL - LIR

STLLIR

Lambert-St Louis

Sun 2/15

6:00 am-1:10 pm

1 stop7h 10m

Liberia

Fri 2/20

8:35 am-10:14 pm

1 stop13h 39m

$342

St. LouisLiberia

STL - LIR

STLLIR

Lambert-St Louis

Mon 5/4

5:20 am-1:40 pm

1 stop9h 20m

Liberia

Wed 5/13

12:29 pm-10:24 pm

1 stop8h 55m

$342

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 2/15

2:22 pm-7:06 am

1 stop16h 44m

San José Juan Santamaria Intl

Mon 3/2

5:51 pm-12:31 pm

1 stop18h 40m

$346

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 2/3

2:22 pm-7:06 am

1 stop16h 44m

San José Juan Santamaria Intl

Sun 2/8

2:54 pm-12:04 am

1 stop9h 10m

$346

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 3/5

2:22 pm-7:05 am

1 stop16h 43m

San José Juan Santamaria Intl

Wed 3/11

2:54 pm-1:04 am

1 stop9h 10m

$346

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 2/21

2:22 pm-8:21 am

1 stop17h 59m

San José Juan Santamaria Intl

Sun 3/1

2:54 pm-12:04 am

1 stop9h 10m

$346

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/13

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, May is the cheapest month in which you can book a flight from Illinois to Costa Rica (average of $236). Flying from Illinois to Costa Rica in March is currently the most expensive (average of $383). 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 January 15, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Costa Rica as you normally would.

Weekly flight availability from Illinois to Costa Rica

Explore weekly flight availability from Illinois to Costa Rica. 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 January 15, 2026.

The most flights from USIL to CR0 are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

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, American Airlines, and Copa Airlines fly from Illinois to Costa Rica in about 7h 10m. The time it takes to get you to your destination can typically vary by up to 9h 34m. 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 $88. Users have also found prices from $96 and $136 on Frontier and Delta, 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, May is the cheapest month in which you can book a flight from Illinois to Costa Rica (average of $236). Flying from Illinois to Costa Rica in March is currently the most expensive (average of $383). 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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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 9 airlines flying from Illinois to Costa Rica

Discover the top 9 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 January 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$206Average$647FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$255Average$381FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$256Average$489FlexibilityNo cancel feeOn-time70%
AviancaCheapest$276Average$437FlexibilityNo cancel feeOn-time71%
FrontierCheapest$345Average$796FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$345Average$678FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$386Average$594FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$394Average$643FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$404Average$675FlexibilityNo cancel feeOn-time69%

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