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$203+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
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 December 18, 2024.

Round-trip from

$328
(eDestinos)

One-way from

$203
(Mytrip)
From Costa Rica to Chicago (CHI)
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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 December 18, 2024.

This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/243:32 pmSJO - ORD
1 stop9h 30mMultiple Airlines
Thu 1/96:06 pmORD - SJO
1 stop17h 12mMultiple Airlines
Deal found 12/16$348
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/311:49 amSJO - ORD
1 stop9h 15mSpirit Airlines
Sun 1/126:06 pmORD - SJO
1 stop17h 12mSpirit Airlines
Deal found 12/17$372
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/233:45 pmSJO - ORD
1 stop20h 30mAvianca
Wed 1/292:35 pmORD - SJO
1 stop18h 45mAvianca
Deal found 12/17$427
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2611:38 amSJO - ORD
1 stop9h 12mFrontier
Sat 1/45:18 pmORD - SJO
1 stop16h 57mFrontier
Deal found 12/16$545
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/258:55 amSJO - ORD
1 stop10h 37mAir Canada
Tue 12/319:50 amORD - SJO
1 stop11h 35mAir Canada
Deal found 12/18$547
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.
Sat 12/211:08 pmSJO - MDW
2 stops19h 37mMultiple Airlines
Sat 1/42:20 pmMDW - SJO
1 stop19h 55mMultiple Airlines
Deal found 12/18$591
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2611:38 amSJO - MDW
1 stop25h 46mFrontier
Sat 1/42:20 pmMDW - SJO
1 stop19h 55mFrontier
Deal found 12/16$615
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.
Sat 12/282:05 pmSJO - ORD
Nonstop5h 25mUnited Airlines
Mon 1/64:15 pmORD - SJO
1 stop7h 43mUnited Airlines
Deal found 12/17$633
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/217:05 amSJO - MDW
1 stop9h 12mDelta
Sat 1/49:30 amMDW - SJO
2 stops12h 25mDelta
Deal found 12/16$660
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/233:45 pmLIR - ORD
1 stop17h 18mSun Country Air
Sun 12/298:03 pmORD - LIR
1 stop18h 41mSun Country Air
Deal found 12/17$709
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.
Wed 12/259:55 amSJO - MDW
2 stops11h 30mSouthwest
Tue 1/77:15 amMDW - SJO
2 stops13h 25mSouthwest
Deal found 12/17$758
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/233:45 pmLIR - ORD
1 stop17h 18mMultiple Airlines
Sun 12/2911:00 amORD - LIR
2 stops27h 44mMultiple Airlines
Deal found 12/17$762

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sun 1/26

1:57 am-10:07 am

1 stop8h 10m

Chicago O'Hare Intl

Mon 1/27

6:06 pm-11:18 am

1 stop17h 12m

$328

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 1/23

8:30 pm-1:15 pm

2 stops16h 45m

Chicago O'Hare Intl

Sun 1/26

2:35 pm-8:40 am

2 stops18h 05m

$338

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 2/4

1:31 pm-11:32 pm

1 stop10h 01m

Chicago O'Hare Intl

Mon 2/10

3:56 pm-12:59 am

3 stops33h 03m

$339

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 1/26

1:57 am-3:02 pm

2 stops13h 05m

Chicago Midway

Mon 2/3

11:33 am-11:18 am

1 stop23h 45m

$405

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 5/1

8:45 am-6:35 pm

1 stop8h 50m

Chicago Midway

Mon 5/5

5:50 am-12:10 pm

1 stop7h 20m

$569

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 12/28

2:15 pm-10:06 pm

1 stop7h 51m

Chicago Midway

Wed 1/8

10:57 am-10:12 pm

1 stop11h 15m

$729

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Fri 1/10

2:45 pm-7:37 pm

2 stops28h 52m

Chicago O'Hare Intl

Mon 1/13

3:56 pm-9:05 am

3 stops17h 09m

$743

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Fri 1/10

2:45 pm-1:11 pm

2 stops22h 26m

Chicago O'Hare Intl

Mon 1/13

8:30 pm-2:30 pm

1 stop18h 00m

$792

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Sat 1/11

8:50 am-7:10 pm

1 stop10h 20m

Chicago O'Hare Intl

Thu 1/23

5:45 am-1:08 pm

1 stop7h 23m

$924

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Sat 1/11

2:29 pm-7:48 pm

Nonstop5h 19m

Chicago O'Hare Intl

Thu 1/23

5:10 am-12:30 pm

1 stop7h 20m

$953

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 40 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, September is the cheapest month in which you can book a flight from Costa Rica to Chicago (average of $232). Flying from Costa Rica to Chicago in June is currently the most expensive (average of $308). 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 December 18, 2024.

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 December 18, 2024.
Read through reviews of airlines operating flights from Costa Rica to Chicago, such as Spirit Airlines, Air Canada and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

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

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

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

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

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

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

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.

Copa Airlines
7.7
Good
1,721 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

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

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

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 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?

    $206 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 Air Canada, with prices starting from $215 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 $1,088, our data shows the cheapest flight currently is $330. When looking at the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl), you can expect to pay $259 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, September is the cheapest month in which you can book a flight from Costa Rica to Chicago (average of $232). Flying from Costa Rica to Chicago in June is currently the most expensive (average of $308). 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.

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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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$205Average$383FlexibilityNo cancel feeOn-time65%
AviancaCheapest$264Average$455FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$404Average$561FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$438Average$703FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$476Average$665FlexibilityNo cancel feeOn-time71%
DeltaCheapest$521Average$680FlexibilityNo cancel feeOn-timeN/A
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