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$176+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJO
dic. 23 — dic. 301
lun. 12/23
lun. 12/30
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 diciembre 18, 2024.

Round-trip from

$348
(eDestinos)

One-way from

$183
(FlightHub)
From Chicago (CHI) to Costa Rica
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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 diciembre 18, 2024.

This Mytrip deal was found by Cheapflights users on 12/17. 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.
mar. 12/3112:09 pmORD - SJO
1 stop12h 45mSpirit Airlines
vie. 5/161:04 amSJO - ORD
1 stop15h 40mSpirit Airlines
Deal found 12/17$384
This Booking.com deal was found by Cheapflights users on 12/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/3112:09 pmORD - SJO
1 stop12h 45mMultiple Airlines
sáb. 5/173:32 pmSJO - ORD
1 stop18h 33mMultiple Airlines
Deal found 12/17$417
This United Airlines deal was found by Cheapflights users on 12/17. 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. 12/3110:35 amORD - SJO
1 stop11h 20mUnited Airlines
sáb. 5/171:00 pmSJO - ORD
Nonstop5h 34mUnited Airlines
Deal found 12/17$626
This Southwest deal was found by Cheapflights users on 12/18. 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.
mié. 12/187:00 amORD - SJO
2 stops13h 40mSouthwest
mié. 12/259:55 amSJO - ORD
2 stops11h 35mSouthwest
Deal found 12/18$703
This American Airlines deal was found by Cheapflights users on 12/17. 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.
jue. 12/195:02 amORD - SJO
1 stop9h 18mAmerican Airlines
mar. 1/143:20 pmSJO - ORD
1 stop17h 10mAmerican Airlines
Deal found 12/17$736
This Kiwi.com deal was found by Cheapflights users on 12/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/316:49 pmMDW - SJO
1 stop16h 52mMultiple Airlines
sáb. 1/1112:25 pmSJO - MDW
1 stop21h 30mMultiple Airlines
Deal found 12/18$743
This Delta deal was found by Cheapflights users on 12/17. 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.
mié. 12/1812:44 pmMDW - SJO
1 stop9h 13mDelta
jue. 12/262:15 pmSJO - MDW
1 stop7h 51mDelta
Deal found 12/17$781
This Delta deal was found by Cheapflights users on 12/17. 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.
mié. 12/181:59 pmORD - SJO
1 stop7h 58mDelta
jue. 12/262:15 pmSJO - ORD
1 stop9h 38mDelta
Deal found 12/17$781
This Southwest deal was found by Cheapflights users on 12/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/191:35 pmMDW - SJO
1 stop7h 05mSouthwest
dom. 12/221:40 pmSJO - MDW
1 stop11h 20mSouthwest
Deal found 12/16$794
This Mytrip deal was found by Cheapflights users on 12/17. 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.
mar. 12/3112:09 pmORD - LIR
2 stops18h 21mMultiple Airlines
sáb. 1/111:20 pmLIR - ORD
2 stops25h 12mMultiple Airlines
Deal found 12/17$844
This Avianca deal was found by Cheapflights users on 12/17. 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.
vie. 12/201:35 pmORD - SJO
1 stop10h 40mAvianca
jue. 12/262:15 amSJO - ORD
1 stop34h 00mAvianca
Deal found 12/17$846
This Southwest deal was found by Cheapflights users on 12/17. 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.
lun. 12/237:40 pmMDW - LIR
2 stops18h 10mSouthwest
dom. 12/293:00 pmLIR - MDW
2 stops9h 20mSouthwest
Deal found 12/17$1,071

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 2,558,603 searches. Data last updated diciembre 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

jue. 1/23

12:37 pm-12:59 am

2 stops12h 22m

San José Juan Santamaria Intl

jue. 1/30

1:31 pm-11:32 pm

1 stop10h 01m

$348

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

lun. 1/20

2:42 am-11:12 pm

1 stop20h 30m

San José Juan Santamaria Intl

lun. 1/27

1:57 am-8:13 pm

1 stop18h 16m

$351

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mar. 2/4

8:15 am-7:35 am

2 stops23h 20m

San José Juan Santamaria Intl

sáb. 2/8

12:25 pm-10:02 am

1 stop21h 37m

$375

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

vie. 2/21

6:48 pm-11:35 am

1 stop16h 47m

San José Juan Santamaria Intl

sáb. 3/1

12:55 pm-10:04 pm

1 stop9h 09m

$382

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

vie. 2/7

1:35 pm-12:15 am

1 stop10h 40m

San José Juan Santamaria Intl

lun. 2/17

2:15 am-12:15 pm

1 stop10h 00m

$422

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

mar. 4/1

1:22 pm-9:29 pm

1 stop9h 07m

San José Juan Santamaria Intl

dom. 4/6

11:34 pm-12:27 pm

1 stop11h 53m

$493

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mié. 2/26

8:25 am-8:40 pm

1 stop12h 15m

San José Juan Santamaria Intl

mar. 3/4

9:55 am-6:50 pm

2 stops8h 55m

$538

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mar. 1/21

12:44 pm-10:12 pm

1 stop9h 28m

San José Juan Santamaria Intl

mar. 1/28

7:00 am-4:21 pm

1 stop9h 21m

$666

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

mar. 2/25

4:05 pm-5:52 pm

3 stops25h 47m

Liberia

sáb. 3/1

7:02 pm-5:53 am

2 stops34h 51m

$702

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

sáb. 1/25

7:25 pm-2:10 pm

2 stops18h 45m

Liberia

dom. 2/9

3:05 pm-10:35 pm

1 stop7h 30m

$710

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 47 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 $531). 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 diciembre 18, 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 diciembre 18, 2024.
Get a feel of what it's like to fly with Delta, Spirit Airlines and United 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
4,848 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,554 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Aeromexico
7.5
Good
1,930 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,055 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 ($183), Frontier ($184), and Air Canada ($247).

  • 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 $604, our data shows the cheapest flight currently is $289. When looking at the most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), you can expect to pay $257 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 $531). 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 Liberia flights
O'Hare Intl to Panama City 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 Liberia flights
Midway to Guatemala City flights
St. Louis to San José flights
Midway to Philip S.W.Goldson flights
O'Hare Intl to Coxen Hole flights
St. Louis to Panama City flights
St. Louis to Philip S.W.Goldson flights
Midway to San Salvador flights
O'Hare Intl to Managua flights
O'Hare Intl to San Pedro Sula flights
St. Louis to Liberia flights
St. Louis to Guatemala City 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
Moline to Philip S.W.Goldson flights
St. Louis to Managua flights
Bloomington to San José flights
St. Louis to San Pedro Sula flights
Moline to Liberia flights
Moline to San Salvador flights
Midway to Tegucigalpa flights
O'Hare Intl to Tegucigalpa flights
Moline to Guatemala City flights
Peoria to San Salvador flights
Springfield to Liberia flights
Evansville to Panama City flights
Bloomington to Philip S.W.Goldson flights
St. Louis to Tegucigalpa 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 diciembre 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$240Average$391FlexibilityNo cancel feeOn-time65%
AviancaCheapest$250Average$433FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$345Average$649FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$413Average$622FlexibilityNo cancel feeOn-time70%
SouthwestCheapest$479Average$613FlexibilityNo cancel feeOn-time63%
DeltaCheapest$554Average$870FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$565Average$748FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$579Average$843FlexibilityNo cancel feeOn-time69%
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