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$124+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJO
mar. 13 — mar. 201
vie. 3/13
vie. 3/20
1 adult, Economy
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Cheap 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 febrero 11, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
mié. 4/221:27 pm
ORD
-
SJO
1 stop22h 55m
Multiple Airlines
mar. 4/2812:31 pm
SJO
-
ORD
2 stops25h 46m
Multiple Airlines
Deal found 2/10$316
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
sáb. 5/165:05 am
ORD
-
SJO
1 stop7h 17m
Spirit Airlines
mié. 5/2712:31 pm
SJO
-
ORD
1 stop10h 10m
Spirit Airlines
Deal found 2/10$317
This FlightHub deal was found by Cheapflights users on 2/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/44:43 pm
ORD
-
SJO
2 stops18h 57m
Spirit Airlines
lun. 3/911:35 am
SJO
-
ORD
2 stops11h 12m
Spirit Airlines
Deal found 2/10$318
This CheapOair deal was found by Cheapflights users on 2/10. 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.
mié. 3/115:15 am
ORD
-
SJO
1 stop7h 07m
Spirit Airlines
lun. 3/1612:19 pm
SJO
-
ORD
2 stops30h 44m
Spirit Airlines
Deal found 2/10$319
This CheapOair deal was found by Cheapflights users on 2/10. 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.
sáb. 2/285:15 am
ORD
-
SJO
1 stop7h 07m
Spirit Airlines
mié. 3/412:35 pm
SJO
-
ORD
1 stop29h 11m
Spirit Airlines
Deal found 2/10$320
This CheapOair deal was found by Cheapflights users on 2/10. 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.
mié. 2/185:15 am
ORD
-
SJO
1 stop7h 07m
Spirit Airlines
mié. 2/251:31 pm
SJO
-
ORD
1 stop7h 42m
Spirit Airlines
Deal found 2/10$321
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
mié. 2/252:22 pm
ORD
-
SJO
1 stop19h 38m
Copa Airlines
mar. 3/32:54 pm
SJO
-
ORD
1 stop9h 10m
Copa Airlines
Deal found 2/9$322
This Copa Airlines deal was found by Cheapflights users on 2/9. 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.
dom. 3/12:22 pm
ORD
-
SJO
3 stops26h 24m
Copa Airlines
dom. 3/88:48 am
SJO
-
ORD
1 stop15h 16m
Copa Airlines
Deal found 2/9$323
This Travelocity deal was found by Cheapflights users on 2/10. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 2/215:05 am
ORD
-
SJO
1 stop8h 10m
Multiple Airlines
jue. 2/261:31 pm
SJO
-
ORD
1 stop10h 16m
Multiple Airlines
Deal found 2/10$324
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
mar. 3/315:05 am
ORD
-
SJO
1 stop7h 09m
Spirit Airlines
sáb. 5/212:31 pm
SJO
-
ORD
1 stop10h 10m
Spirit Airlines
Deal found 2/8$325
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
sáb. 2/289:18 am
ORD
-
SJO
3 stops14h 12m
Multiple Airlines
sáb. 3/71:31 pm
SJO
-
ORD
1 stop7h 42m
Multiple Airlines
Deal found 2/9$326
This United Airlines deal was found by Cheapflights users on 2/9. 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.
mar. 3/38:53 am
ORD
-
SJO
1 stop11h 46m
United Airlines
mar. 3/101:05 pm
SJO
-
ORD
Nonstop5h 30m
United Airlines
Deal found 2/9$327

Find 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 febrero 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$316
(Kiwi.com)

One-way from

$124
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$473

Good round-trip deal

$412 or less

Good one-way deal

$335 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 Illinois to Costa Rica
Search Deals
One-way flight from Illinois to Costa Rica
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Illinois to Costa Rica.
Search Deals
Price to beat on a one-way flight from Illinois to Costa Rica.
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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 febrero 11, 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

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

jue. 4/9

3:21 pm-4:48 pm

3 stops26h 27m

San José Juan Santamaria Intl

jue. 4/16

5:56 pm-1:58 pm

1 stop19h 02m

$319

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

jue. 4/30

3:21 pm-4:47 pm

3 stops26h 26m

San José Juan Santamaria Intl

lun. 5/4

6:19 pm-2:06 pm

1 stop18h 47m

$319

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

jue. 3/5

2:22 pm-4:46 pm

3 stops26h 24m

San José Juan Santamaria Intl

jue. 3/12

11:01 am-1:04 am

1 stop13h 03m

$319

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

lun. 2/23

7:39 am-12:56 pm

Nonstop5h 17m

San José Juan Santamaria Intl

jue. 2/26

2:05 pm-7:35 pm

Nonstop5h 30m

$329

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

mar. 3/10

10:50 am-6:53 pm

1 stop9h 03m

San José Juan Santamaria Intl

mar. 3/17

1:05 pm-7:35 pm

Nonstop5h 30m

$338

St. LouisLiberia

STL - LIR

STLLIR

Lambert-St Louis

lun. 5/4

5:24 am-1:10 pm

1 stop8h 46m

Liberia

mié. 5/13

12:30 pm-10:24 pm

1 stop8h 54m

$342

St. LouisLiberia

STL - LIR

STLLIR

Lambert-St Louis

dom. 4/26

5:21 pm-11:24 am

2 stops19h 03m

Liberia

vie. 5/1

2:10 pm-10:59 pm

1 stop7h 49m

$347

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

dom. 3/8

6:00 am-9:15 pm

1 stop16h 15m

San José Juan Santamaria Intl

mié. 3/18

7:00 am-10:31 pm

1 stop14h 31m

$348

St. LouisLiberia

STL - LIR

STLLIR

Lambert-St Louis

sáb. 3/21

6:57 pm-11:23 am

1 stop17h 26m

Liberia

mié. 3/25

12:21 pm-11:58 pm

1 stop10h 37m

$352

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

dom. 3/8

5:30 am-9:15 pm

1 stop16h 45m

San José Juan Santamaria Intl

mié. 3/18

7:00 am-9:10 am

2 stops25h 10m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

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 $216). Flying from Illinois to Costa Rica in March is currently the most expensive (average of $346). 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 febrero 11, 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 febrero 11, 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 Copa Airlines, United Airlines, and American Airlines fly from Illinois to Costa Rica in about 5h 17m. The time it takes to get you to your destination can typically vary by up to 21h 10m. 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 $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 $216). Flying from Illinois to Costa Rica in March is currently the most expensive (average of $346). 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 febrero 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
AviancaCheapest$148Average$396FlexibilityNo cancel feeOn-time71%
DeltaCheapest$206Average$610FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$248Average$379FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$256Average$469FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$339Average$643FlexibilityNo cancel feeOn-time71%
FrontierCheapest$345Average$796FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$386Average$602FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$393Average$641FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$394Average$640FlexibilityNo cancel feeOn-time63%

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