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$83+ Cheap flights from Chicago (CHI) 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 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheap flight deals from Chicago to Costa Rica

Keep the following information in mind while searching for Chicago to Costa Rica flight deals. Data was last updated July 3, 2025.

Round-trip from

$286
(Priceline)

One-way from

$83
(Priceline)

Popular in

December

Cheapest in

July

Average price

$449

Good round-trip deal

$511 or less

Good one-way deal

$207 or less
From Chicago (CHI) to Costa Rica
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One-way flight from Chicago (CHI) to Costa Rica
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Highest demand for flights based on searches. 9% potential increase in price ($61 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 July 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Costa Rica.
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Price to beat on a one-way flight from Chicago (CHI) to Costa Rica.
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Find flight deals from Chicago to Costa Rica

Cheapest flights from Chicago to Costa Rica
Explore the most affordable flight options available from Chicago to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

This SmartFares deal was found by Cheapflights users on 7/2. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/218:47 pmORD - SJO
2 stops15h 25mSpirit Airlines
Sat 8/2312:18 pmSJO - ORD
2 stops30h 24mSpirit Airlines
Deal found 7/2$302
This Priceline deal was found by Cheapflights users on 7/3. 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.
Sat 8/25:01 amORD - SJO
1 stop8h 30mFrontier
Sat 8/91:47 pmSJO - ORD
1 stop8h 42mFrontier
Deal found 7/3$308
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/245:45 amMDW - SJO
1 stop6h 50mSouthwest
Wed 8/271:40 pmSJO - MDW
1 stop8h 40mSouthwest
Deal found 6/30$322
This American Airlines deal was found by Cheapflights users on 6/30. 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.
Wed 7/96:00 amORD - SJO
1 stop17h 05mAmerican Airlines
Fri 7/1111:59 pmSJO - ORD
1 stop10h 00mAmerican Airlines
Deal found 6/30$322
This CheapOair deal was found by Cheapflights users on 7/1. 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.
Mon 8/255:05 amORD - SJO
1 stop7h 07mMultiple Airlines
Fri 8/294:13 pmSJO - ORD
1 stop17h 52mMultiple Airlines
Deal found 7/1$328
This Copa Airlines deal was found by Cheapflights users on 7/2. 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.
Thu 11/66:56 amORD - SJO
1 stop12h 05mCopa Airlines
Sun 11/94:08 amSJO - ORD
1 stop8h 38mCopa Airlines
Deal found 7/2$337
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 8/169:12 pmMDW - SJO
1 stop14h 20mMultiple Airlines
Sat 8/2312:18 pmSJO - MDW
2 stops24h 38mMultiple Airlines
Deal found 7/2$366
This Air Canada deal was found by Cheapflights users on 7/2. 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.
Thu 11/207:15 amORD - LIR
1 stop30h 35mAir Canada
Tue 11/253:45 pmLIR - ORD
1 stop25h 43mAir Canada
Deal found 7/2$432
This Delta deal was found by Cheapflights users on 7/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/125:45 amORD - LIR
1 stop7h 15mDelta
Thu 8/211:25 pmLIR - ORD
1 stop9h 31mDelta
Deal found 7/2$433
This American Airlines deal was found by Cheapflights users on 7/3. 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.
Tue 8/128:41 pmORD - LIR
2 stops15h 44mAmerican Airlines
Fri 8/2212:30 pmLIR - ORD
1 stop9h 29mAmerican Airlines
Deal found 7/3$437
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/196:00 amMDW - LIR
1 stop7h 00mDelta
Fri 10/241:25 pmLIR - MDW
2 stops18h 20mDelta
Deal found 7/1$437
This United Airlines deal was found by Cheapflights users on 7/1. 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 8/107:52 amORD - LIR
Nonstop5h 01mUnited Airlines
Sat 8/161:03 pmLIR - ORD
Nonstop5h 25mUnited Airlines
Deal found 7/1$438

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago 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 July 3, 2025.
Use the filters below to find and compare flights from Chicago to Costa Rica that are best for you.

Fly from

Chicago

Fly to

Costa Rica

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 8/21

8:47 pm-11:12 am

2 stops15h 25m

San José Juan Santamaria Intl

Sat 8/23

12:18 pm-7:42 pm

2 stops30h 24m

$302

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 8/2

5:01 am-12:31 pm

1 stop8h 30m

San José Juan Santamaria Intl

Sat 8/9

1:47 pm-11:29 pm

1 stop8h 42m

$308

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 8/24

5:45 am-11:35 am

1 stop6h 50m

San José Juan Santamaria Intl

Wed 8/27

1:40 pm-11:20 pm

1 stop8h 40m

$322

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 7/9

6:00 am-10:05 pm

1 stop17h 05m

San José Juan Santamaria Intl

Fri 7/11

11:59 pm-10:59 am

1 stop10h 00m

$322

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 8/25

5:05 am-11:12 am

1 stop7h 07m

San José Juan Santamaria Intl

Fri 8/29

4:13 pm-11:05 am

1 stop17h 52m

$328

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 8/16

9:12 pm-10:32 am

1 stop14h 20m

San José Juan Santamaria Intl

Sat 8/23

12:18 pm-1:56 pm

2 stops24h 38m

$366

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Tue 8/12

5:45 am-12:00 pm

1 stop7h 15m

Liberia

Thu 8/21

1:25 pm-11:56 pm

1 stop9h 31m

$433

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Tue 8/12

8:41 pm-11:25 am

2 stops15h 44m

Liberia

Fri 8/22

12:30 pm-10:59 pm

1 stop9h 29m

$437

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Sun 8/10

7:52 am-11:53 am

Nonstop5h 01m

Liberia

Sat 8/16

1:03 pm-7:28 pm

Nonstop5h 25m

$438

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Sun 7/27

5:15 am-11:35 am

1 stop7h 20m

Liberia

Sat 8/2

11:50 am-11:00 pm

1 stop10h 10m

$454

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 34 results
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Best time to book a flight from Chicago to Costa Rica

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

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

Currently, September is the cheapest month in which you can book a flight from Chicago to Costa Rica (average of $398). Flying from Chicago to Costa Rica in March is currently the most expensive (average of $555). 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 CHI to CR?

Find hourly flight availability from Chicago 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 July 3, 2025.

When flying from Chicago to Costa Rica, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 30% versus a flight in the morning.

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

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

Travelers seeking maximum savings on their Chicago to Costa Rica flight should consider departing on Friday afternoons when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Costa Rica

Get insights into the airlines that provide service to Costa Rica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Costa Rica. Reviews last updated July 3, 2025.
Read reviews from past customers who have flown Alaska Airlines, Porter Airlines, and Southwest from Chicago to Costa Rica. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Porter Airlines
8.0
Very good
298 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Southwest
8.0
Very good
4,266 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Delta
8.0
Very good
7,982 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Copa Airlines
7.5
Good
1,467 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.

Related info for your journey

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

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

    The cheapest airlines for a one-way flight from Chicago to Costa Rica are Frontier ($83), Spirit Airlines ($133), and Alaska Airlines ($210).

  • What are the most popular routes from Chicago to Costa Rica?

    While some choose either Chicago O'Hare Intl - Liberia or Chicago Midway - Liberia, Chicago O'Hare Intl - San José Juan Santamaria Intl is the most popular route from Chicago to Costa Rica.

  • What are the cheapest flights from Chicago to Costa Rica?

    While on average a flight from Chicago to Costa Rica is generally $767, our data shows the cheapest flight currently is $202. When looking at the most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), you can expect to pay $305 for that flight.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Chicago to Costa Rica (average of $398). Flying from Chicago to Costa Rica in March is currently the most expensive (average of $555). 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 Chicago to Costa Rica

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to San José flights
O'Hare Intl to Panama City flights
O'Hare Intl to Liberia flights
O'Hare Intl to Guatemala City flights
Midway to San José flights
Midway to Liberia flights
O'Hare Intl to Philip S.W.Goldson flights
St. Louis to Philip S.W.Goldson flights
O'Hare Intl to San Salvador flights
St. Louis to Panama City flights
O'Hare Intl to San Pedro Sula flights
St. Louis to San José flights
Midway to Guatemala City flights
Midway to Philip S.W.Goldson flights
O'Hare Intl to Managua flights
Midway to Panama City flights
O'Hare Intl to Coxen Hole flights
St. Louis to Liberia flights
Midway to San Salvador flights
Evansville to Panama City flights
Midway to San Pedro Sula flights
St. Louis to Guatemala City flights
St. Louis to Managua flights
St. Louis to San Pedro Sula flights
Moline to Philip S.W.Goldson flights
O'Hare Intl to David flights
St. Louis to Coxen Hole flights
Midway to Managua flights
Bloomington to San José flights
Moline to San Salvador flights
Moline to Liberia flights
Midway to Coxen Hole flights
Moline to San José flights
Moline to Guatemala City flights
Midway to Tegucigalpa flights
O'Hare Intl to Tegucigalpa flights
Bloomington to Philip S.W.Goldson flights
St. Louis to Tegucigalpa flights
Springfield to Liberia flights
Peoria to San Salvador flights

Top 8 airlines flying from Chicago to Costa Rica

Discover the top 8 airlines that operate flights from Chicago 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$274Average$449FlexibilityNo cancel feeOn-time65%
AviancaCheapest$317Average$459FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$345Average$635FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$367Average$608FlexibilityNo cancel feeOn-time70%
DeltaCheapest$438Average$726FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$444Average$717FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$477Average$661FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$480Average$808FlexibilityNo cancel feeOn-time69%

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