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$86+ 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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJO
Nov 16 — Nov 231
Sun 11/16
Sun 11/23
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 October 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$253
(Priceline)

One-way from

$86
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$377

Good round-trip deal

$461 or less

Good one-way deal

$188 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. 12% potential increase in price ($78 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 October 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 October 17, 2025.

This Priceline deal was found by Cheapflights users on 10/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:54 pmORD - SJO
2 stops17h 36mSpirit Airlines
Mon 11/312:34 pmSJO - ORD
2 stops11h 53mSpirit Airlines
Deal found 10/15$253
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/193:26 pmORD - SJO
1 stop20h 49mMultiple Airlines
Fri 12/52:20 amSJO - ORD
1 stop12h 40mMultiple Airlines
Deal found 10/15$254
This Priceline deal was found by Cheapflights users on 10/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/277:51 pmORD - SJO
2 stops16h 39mSpirit Airlines
Thu 10/3012:35 pmSJO - ORD
1 stop11h 28mSpirit Airlines
Deal found 10/16$255
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
Tue 10/215:05 amORD - SJO
1 stop7h 25mSpirit Airlines
Fri 10/3112:35 pmSJO - ORD
1 stop11h 28mSpirit Airlines
Deal found 10/14$256
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
Wed 10/228:00 amORD - SJO
1 stop27h 41mMultiple Airlines
Fri 10/3112:35 pmSJO - ORD
1 stop11h 28mMultiple Airlines
Deal found 10/14$257
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 11/45:10 amORD - SJO
1 stop7h 15mSpirit Airlines
Tue 11/111:30 pmSJO - ORD
1 stop10h 57mSpirit Airlines
Deal found 10/16$258
This KAYAK deal was found by Cheapflights users on 10/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/113:26 pmORD - SJO
1 stop20h 59mSpirit Airlines
Wed 11/191:30 pmSJO - ORD
1 stop10h 57mSpirit Airlines
Deal found 10/14$259
This Cheapflightsfares deal was found by Cheapflights users on 10/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/75:10 amORD - SJO
1 stop7h 15mSpirit Airlines
Wed 11/121:30 pmSJO - ORD
1 stop10h 57mSpirit Airlines
Deal found 10/15$261
This Mytrip deal was found by Cheapflights users on 10/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/276:00 amORD - SJO
1 stop10h 13mMultiple Airlines
Mon 11/31:30 pmSJO - ORD
1 stop10h 57mMultiple Airlines
Deal found 10/14$262
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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.
Thu 11/135:10 amORD - SJO
1 stop7h 15mSpirit Airlines
Thu 11/201:20 pmSJO - ORD
1 stop9h 53mSpirit Airlines
Deal found 10/16$263
This Expedia deal was found by Cheapflights users on 10/16. 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.
Tue 11/185:10 amORD - SJO
1 stop7h 15mSpirit Airlines
Mon 11/241:20 pmSJO - ORD
1 stop9h 53mSpirit Airlines
Deal found 10/16$264
This American Airlines deal was found by Cheapflights users on 10/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/105:17 amSTL - LIR
1 stop9h 01mAmerican Airlines
Sat 11/153:18 pmLIR - STL
1 stop17h 37mAmerican Airlines
Deal found 10/15$283

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 October 17, 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

Fri 11/7

5:56 pm-2:13 pm

2 stops20h 17m

Liberia

Wed 11/12

3:13 pm-10:28 am

2 stops19h 15m

$287

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 11/26

2:07 pm-7:33 am

1 stop17h 26m

San José Juan Santamaria Intl

Mon 12/1

6:07 pm-12:52 pm

1 stop18h 45m

$294

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 11/29

2:07 pm-8:19 am

1 stop18h 12m

San José Juan Santamaria Intl

Tue 12/9

4:08 am-12:52 pm

1 stop8h 44m

$294

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 12/10

5:30 am-10:12 pm

1 stop16h 42m

San José Juan Santamaria Intl

Fri 12/19

7:00 am-6:43 pm

1 stop11h 43m

$306

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Sun 2/22

5:45 am-1:10 pm

1 stop7h 25m

Liberia

Fri 2/27

8:35 am-10:59 pm

1 stop14h 24m

$307

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Sun 2/22

7:55 pm-12:50 pm

1 stop16h 55m

Liberia

Wed 2/25

3:55 pm-10:06 am

1 stop18h 11m

$307

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Sun 1/11

5:40 am-6:37 pm

1 stop12h 57m

Liberia

Fri 1/16

8:35 am-10:58 pm

1 stop14h 23m

$307

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Tue 2/24

5:50 am-2:30 pm

1 stop8h 40m

Liberia

Fri 2/27

3:55 pm-8:39 am

1 stop16h 44m

$307

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Mon 2/23

5:50 am-2:30 pm

1 stop8h 40m

Liberia

Fri 2/27

3:55 pm-10:06 am

1 stop18h 11m

$307

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Tue 2/24

5:50 am-12:50 pm

1 stop7h 00m

Liberia

Wed 2/25

3:55 pm-8:39 am

1 stop16h 44m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/15

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 $245). Flying from Illinois to Costa Rica in December is currently the most expensive (average of $390). 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 October 17, 2025.

Unlike in the morning, 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 evenings when fares are most often at their lowest. Sunday 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 American Airlines, Copa Airlines, and Delta fly from Illinois to Costa Rica in about 16h 42m. The time it takes to get you to your destination can typically vary by up to 3h 35m. Airlines will cover a distance of 2220 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 $99. Users have also found prices from $124 and $132 on Avianca 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 $245). Flying from Illinois to Costa Rica in December is currently the most expensive (average of $390). 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 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 October 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$263Average$427FlexibilityNo cancel feeOn-time65%
DeltaCheapest$290Average$710FlexibilityNo cancel feeOn-timeN/A
AviancaCheapest$307Average$462FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$314Average$525FlexibilityNo cancel feeOn-time70%
FrontierCheapest$345Average$796FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$394Average$645FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$420Average$695FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$432Average$635FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$437Average$756FlexibilityNo cancel feeOn-time69%

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