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$132+ Cheap flights from Costa Rica to Chicago (CHI)

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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Costa Rica to Chicago

Keep the following information in mind while searching for Costa Rica to Chicago flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$310
(Mytrip)

One-way from

$132
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$455

Good round-trip deal

$331 or less

Good one-way deal

$322 or less
Provider with most accurate pricing for San José Juan Santamaria Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-Chicago (CHI) flights.
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From Costa Rica to Chicago (CHI)
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One-way flight from Costa Rica to Chicago (CHI)
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Highest demand for flights based on searches. 7% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Costa Rica to Chicago (CHI).
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Price to beat on a one-way flight from Costa Rica to Chicago (CHI).
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Find flight deals from Costa Rica to Chicago

Cheapest flights from Costa Rica to Chicago
Explore the most affordable flight options available from Costa Rica to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/412:29 pmSJO - ORD
2 stops29h 57mSpirit Airlines
Tue 3/115:55 amORD - SJO
3 stops18h 55mSpirit Airlines
Deal found 2/19$310
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Sat 5/171:24 pmSJO - ORD
1 stop8h 04mMultiple Airlines
Wed 5/215:05 amORD - SJO
1 stop7h 13mMultiple Airlines
Deal found 2/19$323
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Tue 4/811:55 amSJO - MDW
1 stop10h 29mMultiple Airlines
Tue 4/156:00 amMDW - SJO
1 stop17h 40mMultiple Airlines
Deal found 2/19$328
This JetBlue deal was found by Cheapflights users on 2/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2511:44 pmSJO - ORD
1 stop11h 03mJetBlue
Tue 3/411:44 amORD - SJO
1 stop10h 04mJetBlue
Deal found 2/19$431
This Copa Airlines deal was found by Cheapflights users on 2/20. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/18:07 amSJO - ORD
1 stop15h 14mCopa Airlines
Thu 11/66:56 amORD - SJO
1 stop12h 11mCopa Airlines
Deal found 2/20$437
This eDestinos deal was found by Cheapflights users on 2/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/71:42 pmSJO - MDW
1 stop27h 07mFrontier
Fri 6/136:44 pmMDW - SJO
1 stop18h 38mFrontier
Deal found 2/19$441
This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/78:00 pmSJO - ORD
2 stops17h 25mAvianca
Fri 6/132:35 pmORD - SJO
1 stop19h 45mAvianca
Deal found 2/19$465
This Southwest deal was found by Cheapflights users on 2/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/161:10 pmSJO - MDW
1 stop9h 25mSouthwest
Tue 5/208:45 amMDW - SJO
1 stop11h 55mSouthwest
Deal found 2/19$523
This Delta deal was found by Cheapflights users on 2/20. 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.
Tue 3/181:21 pmSJO - MDW
1 stop8h 02mDelta
Wed 3/2612:51 pmMDW - SJO
1 stop9h 33mDelta
Deal found 2/20$524
This United Airlines deal was found by Cheapflights users on 2/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/81:03 pmLIR - ORD
Nonstop5h 25mUnited Airlines
Tue 6/179:40 pmORD - LIR
1 stop13h 20mUnited Airlines
Deal found 2/20$652
This American Airlines deal was found by Cheapflights users on 2/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/82:45 pmLIR - ORD
1 stop8h 13mAmerican Airlines
Tue 6/175:07 amORD - LIR
2 stops9h 12mAmerican Airlines
Deal found 2/20$825
This Alaska Airlines deal was found by Cheapflights users on 2/20. 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.
Fri 6/1310:00 amLIR - ORD
2 stops42h 04mAlaska Airlines
Sat 6/217:59 pmORD - LIR
2 stops25h 16mAlaska Airlines
Deal found 2/20$847

Find flights from Costa Rica to Chicago within your budget

Customize your flight search to find flights from Costa Rica to Chicago 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 February 20, 2025.

Fly from

Costa Rica

Fly to

Chicago

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 3/4

12:29 pm-6:26 pm

2 stops29h 57m

Chicago O'Hare Intl

Tue 3/11

5:55 am-11:50 pm

3 stops18h 55m

$310

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 5/17

1:24 pm-10:28 pm

1 stop8h 04m

Chicago O'Hare Intl

Wed 5/21

5:05 am-11:18 am

1 stop7h 13m

$323

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 4/8

11:55 am-11:24 pm

1 stop10h 29m

Chicago Midway

Tue 4/15

6:00 am-10:40 pm

1 stop17h 40m

$328

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Mon 3/3

4:09 am-12:42 pm

1 stop8h 33m

Chicago O'Hare Intl

Sun 3/9

7:55 am-7:07 pm

1 stop12h 12m

$437

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 6/7

1:42 pm-5:49 pm

1 stop27h 07m

Chicago Midway

Fri 6/13

6:44 pm-12:22 pm

1 stop18h 38m

$441

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 6/7

8:00 pm-2:25 pm

2 stops17h 25m

Chicago O'Hare Intl

Fri 6/13

2:35 pm-9:20 am

1 stop19h 45m

$465

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 5/16

1:10 pm-11:35 pm

1 stop9h 25m

Chicago Midway

Tue 5/20

10:25 am-7:40 pm

2 stops10h 15m

$523

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 3/18

7:00 am-6:02 pm

2 stops10h 02m

Chicago Midway

Wed 4/2

9:25 am-9:24 pm

2 stops12h 59m

$524

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Sun 6/8

1:03 pm-7:28 pm

Nonstop5h 25m

Chicago O'Hare Intl

Tue 6/17

9:40 pm-10:00 am

1 stop13h 20m

$652

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Sun 6/8

2:45 pm-11:58 pm

1 stop8h 13m

Chicago O'Hare Intl

Tue 6/17

5:07 am-1:19 pm

2 stops9h 12m

$825

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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

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

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

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

Currently, August is the cheapest month in which you can book a flight from Costa Rica to Chicago (average of $245). Flying from Costa Rica to Chicago in March is currently the most expensive (average of $321). 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 CR to CHI?

Find hourly flight availability from Costa Rica to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

It’s typically best to fly out from Costa Rica to Chicago at noon. Doing so could potentially save you 7% on the flight price compared to flying in the morning, which is usually more expensive.

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

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

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

Rainfall in Chicago by month

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

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated February 20, 2025.
Read through reviews of airlines operating flights from Costa Rica to Chicago, such as Southwest, Alaska Airlines and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Copa Airlines
7.6
Good
1,510 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Costa Rica to Chicago. 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 Costa Rica to Chicago one-way?

    $138 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and JetBlue, with prices starting from $154 and $238, respectively.

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

    When deciding which route to take from Costa Rica to Chicago consider San José Juan Santamaria Intl - Chicago O'Hare Intl, San José Juan Santamaria Intl - Chicago Midway or Liberia - Chicago O'Hare Intl as they are the most popular.

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

    While on average a flight from Costa Rica to Chicago is generally $1,051, our data shows the cheapest flight currently is $242. When looking at the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl), you can expect to pay $247 for that flight.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Costa Rica to Chicago (average of $245). Flying from Costa Rica to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Costa Rica?

Book flights to Costa Rica if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Costa Rica to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Costa Rica to Chicago

Discover the top 6 airlines that operate flights from Costa Rica to Chicago. 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$205Average$385FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$320Average$587FlexibilityNo cancel feeOn-time70%
AviancaCheapest$371Average$474FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$438Average$716FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$476Average$660FlexibilityNo cancel feeOn-time71%
DeltaCheapest$521Average$649FlexibilityNo cancel feeOn-timeN/A
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