Costa Rica

$172+ Cheap flights from Illinois to Costa Rica

ORD — SJO
Dec 5 — Dec 121
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Cheap flight deals from Illinois to Costa Rica

Cheapest flights from Illinois to Costa Rica

Mon 11/233:50 pm -
1 stop22h 30m
Tue 12/13:20 pm -
1 stop23h 52m
Deal found 10/31$390
Mon 11/168:40 pm -
1 stop17h 30m
Wed 12/163:20 pm -
1 stop23h 42m
Deal found 11/1$415
Mon 12/78:40 pm -
1 stop17h 30m
Fri 12/113:10 pm -
1 stop17h 58m
Deal found 10/31$420
Mon 12/710:30 pm -
1 stop17h 50m
Sat 12/129:30 am -
1 stop11h 00m
Deal found 11/2$424
Thu 11/1910:30 pm -
1 stop10h 20m
Wed 12/21:50 am -
1 stop18h 40m
Deal found 11/2$425
Thu 12/32:20 pm -
1 stop18h 15m
Sun 12/61:50 am -
1 stop18h 40m
Deal found 11/1$427
Thu 12/102:20 pm -
1 stop18h 15m
Tue 12/155:35 am -
1 stop7h 20m
Deal found 11/2$430
Sun 11/295:30 am -
1 stop16h 45m
Tue 12/82:37 pm -
1 stop9h 19m
Deal found 11/3$439
Sun 11/295:30 am -
1 stop16h 45m
Wed 12/92:37 pm -
2 stops17h 22m
Deal found 11/3$443
Thu 11/1910:30 pm -
1 stop17h 50m
Sat 11/211:55 am -
1 stop18h 35m
Deal found 11/3$444
Thu 12/32:20 pm -
1 stop8h 55m
Tue 12/89:30 am -
1 stop11h 00m
Deal found 11/3$447
Fri 12/42:20 pm -
1 stop18h 15m
Fri 12/115:15 pm -
1 stop27h 15m
Deal found 11/1$450

Find flight deals from Illinois to Costa Rica

Most accurate provider

Ovago
3 stars

Most trusted provider

Ovago
3 stars

Round-trip from

$390
(Trip.com)

One-way from

$172
(Mytrip)

Popular in

December

Cheapest in

February

Average price

$538

Good round-trip deal

$574 or less

Good one-way deal

$283 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 Illinois to Costa Rica
One-way flight from Illinois to Costa Rica
Highest demand for flights based on searches. 1% potential increase in price ($5 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
Average for round-trip flights in November 2026
Price to beat on a round-trip flight from Illinois to Costa Rica.
Price to beat on a one-way flight from Illinois to Costa Rica.

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Illinois to Costa Rica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoLiberia

ORD Chicago O'Hare Intl - LIR Liberia

ORDLIR

Chicago O'Hare Intl

Tue 12/8

1:55 pm-2:20 pm

2 stops24h 25m

Liberia

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$197

ChicagoLiberia

ORD Chicago O'Hare Intl - LIR Liberia

ORDLIR

Chicago O'Hare Intl

Wed 12/30

10:03 am-3:20 pm

Nonstop5h 17m

Liberia

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$260

ChicagoLiberia

MDW Chicago Midway - LIR Liberia

MDWLIR

Chicago Midway

Mon 1/4

6:00 am-12:45 pm

1 stop6h 45m

Liberia

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$264

ChicagoLiberia

ORD Chicago O'Hare Intl - LIR Liberia

ORDLIR

Chicago O'Hare Intl

Sat 1/2

7:00 am-2:04 pm

1 stop7h 04m

Liberia

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$264

ChicagoLiberia

ORD Chicago O'Hare Intl - LIR Liberia

ORDLIR

Chicago O'Hare Intl

Tue 12/29

5:25 am-12:45 pm

1 stop7h 20m

Liberia

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$274

ChicagoLiberia

ORD Chicago O'Hare Intl - LIR Liberia

ORDLIR

Chicago O'Hare Intl

Tue 11/24

8:40 pm-2:10 pm

1 stop17h 30m

Liberia

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$297

ChicagoLiberia

MDW Chicago Midway - LIR Liberia

MDWLIR

Chicago Midway

Sun 12/6

8:25 pm-1:50 pm

2 stops17h 25m

Liberia

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$318

ChicagoLiberia

MDW Chicago Midway - LIR Liberia

MDWLIR

Chicago Midway

Fri 2/19

5:20 am-2:15 pm

1 stop8h 55m

Liberia

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$322

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Fri 4/30

10:15 am-7:00 pm

2 stops9h 45m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$323

ChicagoLiberia

ORD Chicago O'Hare Intl - LIR Liberia

ORDLIR

Chicago O'Hare Intl

Tue 12/15

5:30 pm-11:54 am

1 stop18h 24m

Liberia

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 60 resultsSorted by cheapest first
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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

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, February is the cheapest month in which you can book a flight from Illinois to Costa Rica (average of $528). Flying from Illinois to Costa Rica in December is currently the most expensive (average of $795). 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?

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.

How far ahead should I book a flight from Illinois to Costa Rica?

The price you pay for your flight from Illinois to Costa Rica may vary depending on when you book. For the best chance of a lower fare, look to book 24 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

Related info for your journey

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

    Airlines like Copa Airlines, Delta, and United Airlines fly from Illinois to Costa Rica in about 5h 13m. The time it takes to get you to your destination can typically vary by up to 11h 56m. 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 Frontier. According to our data, you can fly for as low as $96. Users have also found prices from $149 and $154 on Copa Airlines and Southwest, 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, February is the cheapest month in which you can book a flight from Illinois to Costa Rica (average of $528). Flying from Illinois to Costa Rica in December is currently the most expensive (average of $795). 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

Alternative routes for Illinois to Costa Rica

Top 9 airlines flying from Illinois to Costa Rica

AirlineCheapestAverageFlexibilityOn-time
AviancaCheapest$149Average$565FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$303Average$545FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$324Average$578FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$364Average$640FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$371Average$626FlexibilityNo cancel feeOn-time62%
DeltaCheapest$378Average$601FlexibilityNo cancel feeOn-timeN/A
GOLCheapest$384Average$825FlexibilityNo cancel feeOn-time74%
United AirlinesCheapest$392Average$671FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$395Average$658FlexibilityNo cancel feeOn-time63%

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