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$198+ 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 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Costa Rica to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Costa Rica (CR0) to Chicago (CHI). 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 January 21, 2025.

Round-trip from

$327
(Kiwi.com)

One-way from

$199
(Orbitz)

Good round-trip deal

$440 or less

Good one-way deal

$340 or less
From Costa Rica to Chicago (CHI)
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One-way flight from Costa Rica to Chicago (CHI)
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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 January 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/1912:29 pmSJO - ORD
1 stop18h 40mMultiple Airlines
Wed 2/265:00 amORD - SJO
1 stop7h 20mMultiple Airlines
Deal found 1/21$327
This eDestinos deal was found by Cheapflights users on 1/21. 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 2/81:57 amSJO - ORD
1 stop8h 20mSpirit Airlines
Mon 2/245:00 amORD - SJO
1 stop7h 20mSpirit Airlines
Deal found 1/21$329
This Cheapflightsfares deal was found by Cheapflights users on 1/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/132:15 amSJO - ORD
1 stop10h 00mAvianca
Tue 3/253:05 pmORD - SJO
1 stop19h 15mAvianca
Deal found 1/20$384
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/124:09 amSJO - MDW
2 stops11h 04mMultiple Airlines
Thu 2/2012:43 pmMDW - SJO
1 stop22h 41mMultiple Airlines
Deal found 1/20$431
This Southwest deal was found by Cheapflights users on 1/20. 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.
Tue 5/61:10 pmSJO - MDW
1 stop8h 40mSouthwest
Sun 5/189:35 amMDW - SJO
2 stops11h 05mSouthwest
Deal found 1/20$548
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Fri 3/141:01 pmLIR - ORD
Nonstop5h 19mUnited Airlines
Sun 3/238:17 pmORD - LIR
1 stop16h 51mUnited Airlines
Deal found 1/20$621
This Air Canada deal was found by Cheapflights users on 1/20. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/92:30 pmLIR - ORD
1 stop17h 25mAir Canada
Fri 4/183:35 pmORD - LIR
1 stop21h 55mAir Canada
Deal found 1/20$639
This Delta deal was found by Cheapflights users on 1/21. 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.
Wed 10/11:18 pmSJO - MDW
1 stop7h 29mDelta
Wed 10/86:00 amMDW - SJO
1 stop6h 48mDelta
Deal found 1/21$651
This eDestinos deal was found by Cheapflights users on 1/20. 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 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 1/20$659
This Alaska Airlines deal was found by Cheapflights users on 1/20. 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 3/77:02 pmLIR - ORD
2 stops28h 57mAlaska Airlines
Tue 3/115:54 pmORD - LIR
2 stops23h 58mAlaska Airlines
Deal found 1/20$659
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/76:40 amLIR - ORD
2 stops21h 57mMultiple Airlines
Mon 3/101:48 amORD - LIR
2 stops17h 42mMultiple Airlines
Deal found 1/20$743
This American Airlines deal was found by Cheapflights users on 1/20. 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.
Fri 3/142:05 pmLIR - ORD
1 stop9h 13mAmerican Airlines
Sun 3/236:58 pmORD - LIR
1 stop17h 42mAmerican Airlines
Deal found 1/20$804

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 2/19

12:29 pm-7:09 am

1 stop18h 40m

Chicago O'Hare Intl

Wed 2/26

5:00 am-12:20 pm

1 stop7h 20m

$327

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 2/8

1:57 am-10:17 am

1 stop8h 20m

Chicago O'Hare Intl

Mon 2/24

5:00 am-12:20 pm

1 stop7h 20m

$329

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 3/13

2:15 am-1:15 pm

1 stop10h 00m

Chicago O'Hare Intl

Tue 3/25

3:05 pm-9:20 am

1 stop19h 15m

$384

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 2/12

4:09 am-3:13 pm

2 stops11h 04m

Chicago Midway

Thu 2/20

12:43 pm-11:24 am

1 stop22h 41m

$431

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 5/6

1:10 pm-10:50 pm

1 stop8h 40m

Chicago Midway

Sun 5/18

9:35 am-7:40 pm

2 stops11h 05m

$548

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Fri 3/14

1:01 pm-7:20 pm

Nonstop5h 19m

Chicago O'Hare Intl

Sun 3/23

8:17 pm-12:08 pm

1 stop16h 51m

$621

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Wed 4/9

2:30 pm-8:55 am

1 stop17h 25m

Chicago O'Hare Intl

Fri 4/18

3:35 pm-12:30 pm

1 stop21h 55m

$639

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 3/26

12:51 pm-9:24 pm

1 stop9h 33m

$651

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

$659

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Fri 3/7

7:02 pm-11:59 pm

2 stops28h 57m

Chicago O'Hare Intl

Tue 3/11

5:54 pm-4:52 pm

2 stops23h 58m

$659

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 35 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 $320). 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 January 21, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Costa Rica to Chicago as you normally would.

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 January 21, 2025.
Read through reviews of airlines operating flights from Costa Rica to Chicago, such as United Airlines, Spirit Airlines and Air Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

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
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

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
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

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
9,706 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

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.

Copa Airlines
7.7
Good
1,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

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
1,849 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

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 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?

    $200 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 Avianca and Frontier, with prices starting from $216 and $256, 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 $1,044, our data shows the cheapest flight currently is $305. When looking at the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl), you can expect to pay $289 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 $320). 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

Browse thousands of different options on Cheapflights for your next trip

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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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San Pedro Sula to Midway flights
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Managua to Midway flights
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Managua to St. Louis flights
Tegucigalpa to St. Louis flights
Tegucigalpa to O'Hare Intl flights
Tegucigalpa to Midway flights

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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$205Average$380FlexibilityNo cancel feeOn-time65%
AviancaCheapest$290Average$467FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$404Average$561FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$438Average$704FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$476Average$681FlexibilityNo cancel feeOn-time71%
DeltaCheapest$521Average$649FlexibilityNo cancel feeOn-timeN/A
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