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$119+ 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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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Cheap flight deals from Chicago to Costa Rica

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Costa Rica (CR0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 20, 2024.

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 November 20, 2024.

This FlightHub deal was found by Cheapflights users on 11/19. 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.
Tue 12/310:25 amORD - SJO
1 stop14h 36mSpirit Airlines
Mon 12/91:49 amSJO - ORD
1 stop7h 48mSpirit Airlines
Deal found 11/19$355
This CheapOair deal was found by Cheapflights users on 11/19. 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.
Fri 12/65:10 amORD - SJO
2 stops30h 18mMultiple Airlines
Mon 12/92:53 pmSJO - ORD
1 stop13h 44mMultiple Airlines
Deal found 11/19$362
This Avianca deal was found by Cheapflights users on 11/20. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/42:35 pmORD - SJO
1 stop18h 45mAvianca
Thu 12/128:30 pmSJO - ORD
2 stops16h 45mAvianca
Deal found 11/20$404
This Lucky2Go deal was found by Cheapflights users on 11/19. 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 Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/22:55 pmMDW - SJO
2 stops20h 36mMultiple Airlines
Wed 12/41:49 amSJO - MDW
1 stop13h 23mMultiple Airlines
Deal found 11/19$479
This Southwest deal was found by Cheapflights users on 11/20. 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.
Wed 12/411:00 amMDW - SJO
1 stop9h 40mSouthwest
Tue 12/109:55 amSJO - MDW
2 stops12h 25mSouthwest
Deal found 11/20$573
This Delta deal was found by Cheapflights users on 11/19. 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.
Sat 11/3010:41 amMDW - SJO
1 stop11h 12mDelta
Sat 12/72:13 pmSJO - MDW
1 stop7h 53mDelta
Deal found 11/19$629
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 12/411:45 amORD - LIR
2 stops18h 45mMultiple Airlines
Sat 12/143:40 pmLIR - ORD
1 stop19h 55mMultiple Airlines
Deal found 11/19$725
This Air Canada deal was found by Cheapflights users on 11/18. 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.
Fri 11/298:25 pmORD - LIR
1 stop18h 05mAir Canada
Sat 12/73:30 pmLIR - ORD
1 stop17h 27mAir Canada
Deal found 11/18$732
This Alaska Airlines deal was found by Cheapflights users on 11/20. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/77:00 amORD - LIR
2 stops24h 31mAlaska Airlines
Wed 12/117:34 pmLIR - ORD
2 stops21h 25mAlaska Airlines
Deal found 11/20$741
This Southwest deal was found by Cheapflights users on 11/18. 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.
Fri 11/297:00 amMDW - LIR
1 stop7h 05mSouthwest
Sat 12/71:35 pmLIR - MDW
1 stop8h 55mSouthwest
Deal found 11/18$826
This Mytrip deal was found by Cheapflights users on 11/18. 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.
Fri 11/299:30 amMDW - LIR
3 stops30h 30mMultiple Airlines
Sat 12/75:10 pmLIR - MDW
2 stops20h 21mMultiple Airlines
Deal found 11/18$900
This Delta deal was found by Cheapflights users on 11/20. 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.
Thu 12/197:05 amORD - LIR
1 stop7h 27mDelta
Wed 12/253:57 pmLIR - ORD
1 stop7h 59mDelta
Deal found 11/20$912

Find flights from Chicago to Costa Rica within your budget

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 2/3

3:22 pm-12:26 pm

1 stop21h 04m

San José Juan Santamaria Intl

Mon 2/10

12:25 pm-12:03 pm

2 stops47h 38m

$353

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 1/7

8:14 pm-12:54 am

3 stops28h 40m

San José Juan Santamaria Intl

Mon 4/7

2:52 pm-5:44 am

1 stop13h 52m

$356

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 12/4

2:35 pm-9:20 am

1 stop18h 45m

San José Juan Santamaria Intl

Thu 12/12

8:30 pm-1:15 pm

2 stops16h 45m

$404

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 12/2

2:55 pm-11:31 am

2 stops20h 36m

San José Juan Santamaria Intl

Wed 12/4

1:49 am-3:12 pm

1 stop13h 23m

$479

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 2/26

8:25 am-8:40 pm

1 stop12h 15m

San José Juan Santamaria Intl

Tue 3/4

9:55 am-6:50 pm

2 stops8h 55m

$489

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 11/30

10:41 am-9:53 pm

1 stop11h 12m

San José Juan Santamaria Intl

Sat 12/7

2:13 pm-10:06 pm

1 stop7h 53m

$629

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Sun 2/23

7:00 pm-5:01 pm

2 stops22h 01m

Liberia

Sat 3/1

6:13 pm-4:58 pm

1 stop22h 45m

$682

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Wed 1/15

8:40 pm-2:10 pm

2 stops17h 30m

Liberia

Sat 2/1

1:30 pm-9:35 am

2 stops20h 05m

$685

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Tue 3/25

11:35 am-12:45 pm

1 stop26h 10m

Liberia

Thu 4/3

1:45 pm-2:45 pm

1 stop24h 00m

$706

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Wed 12/4

11:45 am-6:30 am

2 stops18h 45m

Liberia

Sat 12/14

3:40 pm-11:35 am

1 stop19h 55m

$725

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 42 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.

Travel insights for flights from Chicago to Costa Rica

Get recent, data-driven insights about flights from Chicago to Costa Rica including ideal travel times, pricing trends, and more.

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 July is currently the most expensive (average of $532). 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 November 20, 2024.

When flying from Chicago to Costa Rica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Costa Rica by month

Plan your trip to Costa Rica by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Costa Rica ranges from 0.0 - 11.8 inches per month. September is typically the wettest month, when rainfall can reach 11.8 in. February is typically the driest time to visit Costa Rica when rainfall is around 0.0 in.

Temperature in Costa Rica by month

Plan your trip to Costa Rica by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Costa Rica, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 64.4 F).

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 November 20, 2024.
Get a feel of what it's like to fly with Avianca, Southwest and Spirit Airlines from Chicago to Costa Rica by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,461 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Aeromexico
7.5
Good
2,004 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 Spirit Airlines ($136), Southwest ($202), and Frontier ($208).

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

    While some choose either Chicago O'Hare Intl - Liberia or Chicago Midway - San José Juan Santamaria Intl, 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 $653, our data shows the cheapest flight currently is $309. When looking at the most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), you can expect to pay $273 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 July is currently the most expensive (average of $532). 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
O'Hare Intl to Philip S.W.Goldson flights
Midway to San José flights
O'Hare Intl to San Salvador flights
Midway to Panama City flights
Midway to Guatemala City flights
St. Louis to San José flights
Midway to Liberia flights
Midway to Philip S.W.Goldson flights
O'Hare Intl to Managua flights
O'Hare Intl to Coxen Hole flights
Midway to San Salvador flights
St. Louis to Philip S.W.Goldson flights
O'Hare Intl to San Pedro Sula flights
St. Louis to Panama City flights
St. Louis to Guatemala City flights
St. Louis to Liberia flights
St. Louis to Coxen Hole flights
Midway to San Pedro Sula flights
Midway to Managua flights
Moline to San José flights
Midway to Coxen Hole flights
O'Hare Intl to David flights
Evansville to Panama City flights
St. Louis to Managua flights
Moline to San Salvador flights
Moline to Liberia flights
Moline to Philip S.W.Goldson flights
O'Hare Intl to Tegucigalpa flights
St. Louis to San Pedro Sula flights
Moline to Guatemala City flights
Midway to Tegucigalpa flights
Bloomington to San José flights
Bloomington to Philip S.W.Goldson flights
Springfield to Liberia flights
St. Louis to Tegucigalpa flights
Peoria to San Salvador flights

Top 10 airlines flying from Chicago to Costa Rica

Discover the top 10 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$237Average$384FlexibilityNo cancel feeOn-time65%
AviancaCheapest$238Average$412FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$345Average$649FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$406Average$613FlexibilityNo cancel feeOn-time70%
SouthwestCheapest$479Average$600FlexibilityNo cancel feeOn-time63%
Air CanadaCheapest$479Average$651FlexibilityNo cancel feeOn-time67%
DeltaCheapest$550Average$885FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$565Average$753FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$581Average$850FlexibilityNo cancel feeOn-time69%
AeromexicoCheapest$676Average$736FlexibilityNo cancel feeOn-timeN/A
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