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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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$291
(Kiwi.com)

One-way from

$132
(eDestinos)

Popular in

December

Cheapest in

August

Average price

$443

Good round-trip deal

$478 or less

Good one-way deal

$255 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. 3% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/30. 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 5/2912:28 pmSJO - ORD
1 stop10h 37mMultiple Airlines
Sat 6/75:08 pmORD - SJO
1 stop18h 19mMultiple Airlines
Deal found 4/30$291
This Mytrip deal was found by Cheapflights users on 4/30. 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 5/3011:32 amSJO - ORD
2 stops24h 10mSpirit Airlines
Wed 6/47:37 amORD - SJO
1 stop27h 50mSpirit Airlines
Deal found 4/30$297
This Copa Airlines deal was found by Cheapflights users on 4/30. 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.
Thu 8/284:10 amSJO - ORD
1 stop8h 32mCopa Airlines
Mon 9/17:54 amORD - SJO
1 stop9h 58mCopa Airlines
Deal found 4/30$311
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 8/25:05 amSJO - ORD
1 stop10h 00mAvianca
Sun 8/103:45 pmORD - SJO
1 stop18h 35mAvianca
Deal found 4/30$312
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Sun 6/84:10 amSJO - MDW
2 stops15h 07mMultiple Airlines
Thu 6/129:12 pmMDW - SJO
1 stop14h 25mMultiple Airlines
Deal found 4/30$375
This Southwest deal was found by Cheapflights users on 4/30. 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.
Thu 8/281:40 pmSJO - MDW
1 stop9h 25mSouthwest
Tue 9/29:00 amMDW - SJO
2 stops10h 55mSouthwest
Deal found 4/30$430
This United Airlines deal was found by Cheapflights users on 4/30. 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 6/11:00 pmSJO - ORD
Nonstop5h 34mUnited Airlines
Sat 6/76:00 amORD - SJO
1 stop17h 39mUnited Airlines
Deal found 4/30$432
This Delta deal was found by Cheapflights users on 4/30. 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 5/31:20 pmSJO - MDW
1 stop8h 02mDelta
Sat 5/106:00 amMDW - SJO
1 stop8h 05mDelta
Deal found 4/30$435
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Mon 5/51:50 pmSJO - ORD
1 stop16h 35mAmerican Airlines
Sat 5/109:45 amORD - SJO
2 stops9h 50mAmerican Airlines
Deal found 4/29$448
This United Airlines deal was found by Cheapflights users on 4/29. 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 6/133:25 pmLIR - ORD
1 stop7h 48mUnited Airlines
Fri 6/209:40 pmORD - LIR
1 stop17h 43mUnited Airlines
Deal found 4/29$458
This Delta deal was found by Cheapflights users on 4/28. 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 8/231:25 pmLIR - ORD
1 stop9h 30mDelta
Tue 9/306:00 amORD - LIR
1 stop7h 00mDelta
Deal found 4/28$505
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Sat 8/231:59 pmLIR - ORD
1 stop8h 44mAmerican Airlines
Sun 9/286:00 amORD - LIR
1 stop8h 01mAmerican Airlines
Deal found 4/28$509

Cheapflights Fare Finder

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 May 1, 2025.
Use the filters below to find and compare flights from Costa Rica to Chicago that are best for you.

Fly from

Costa Rica

Fly to

Chicago

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 5/29

12:28 pm-12:05 am

1 stop10h 37m

Chicago O'Hare Intl

Sat 6/7

5:08 pm-10:27 am

1 stop18h 19m

$291

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 5/30

11:32 am-12:42 pm

2 stops24h 10m

Chicago O'Hare Intl

Wed 6/4

7:37 am-10:27 am

1 stop27h 50m

$297

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 8/28

4:10 am-1:42 pm

1 stop8h 32m

Chicago O'Hare Intl

Mon 9/1

7:54 am-4:52 pm

1 stop9h 58m

$311

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 8/2

5:05 am-4:05 pm

1 stop10h 00m

Chicago O'Hare Intl

Sun 8/10

3:45 pm-9:20 am

1 stop18h 35m

$312

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 6/8

4:10 am-8:17 pm

2 stops15h 07m

Chicago Midway

Thu 6/12

9:12 pm-10:37 am

1 stop14h 25m

$375

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 8/28

1:40 pm-12:05 am

1 stop9h 25m

Chicago Midway

Tue 9/2

9:00 am-6:55 pm

2 stops10h 55m

$430

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sun 6/1

1:00 pm-7:34 pm

Nonstop5h 34m

Chicago O'Hare Intl

Sat 6/7

6:00 am-10:39 pm

1 stop17h 39m

$432

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 5/15

6:03 am-6:11 pm

1 stop11h 08m

Chicago O'Hare Intl

Wed 5/21

8:22 am-6:35 pm

2 stops11h 13m

$448

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Fri 6/13

3:25 pm-12:13 am

1 stop7h 48m

Chicago O'Hare Intl

Fri 6/20

9:40 pm-2:23 pm

1 stop17h 43m

$458

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 9/15

1:18 pm-9:44 pm

1 stop7h 26m

Chicago Midway

Fri 9/19

6:00 am-11:53 am

1 stop6h 53m

$478

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 29 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.

Cheapflights Insights

Everything you need to know about your flight from Costa Rica to Chicago

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 May 1, 2025.

It’s typically best to fly out from Costa Rica to Chicago at noon. Doing so could potentially save you 11% 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 May 1, 2025.
Read through reviews of airlines operating flights from Costa Rica to Chicago, such as Alaska Airlines, Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,294 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Copa Airlines
7.5
Good
1,414 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Aeromexico
7.5
Good
1,698 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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?

    $132 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 United Airlines, with prices starting from $178 and $243, 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 $402, our data shows the cheapest flight currently is $235. 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, 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
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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$242Average$406FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$311Average$506FlexibilityNo cancel feeOn-time70%
AviancaCheapest$321Average$491FlexibilityNo cancel feeOn-time71%
DeltaCheapest$434Average$563FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$438Average$730FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$446Average$569FlexibilityNo cancel feeOn-time71%

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