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$108+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$227
(Kiwi.com)

One-way from

$108
(eDestinos)

Popular in

June

Cheapest in

November

Average price

$410

Good round-trip deal

$325 or less

Good one-way deal

$175 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. 4% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Fri 12/51:31 pmSJO - ORD
1 stop30h 30mSpirit Airlines
Wed 12/103:26 pmORD - SJO
1 stop20h 59mSpirit Airlines
Deal found 11/4$227
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 11/221:20 pmSJO - ORD
1 stop10h 09mSpirit Airlines
Tue 12/24:58 pmORD - SJO
1 stop17h 21mSpirit Airlines
Deal found 11/4$232
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Mon 12/81:31 pmSJO - ORD
1 stop21h 37mSpirit Airlines
Wed 12/103:26 pmORD - SJO
1 stop20h 59mSpirit Airlines
Deal found 11/4$239
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Fri 12/51:31 pmSJO - ORD
1 stop30h 30mMultiple Airlines
Thu 12/116:15 amORD - SJO
1 stop30h 10mMultiple Airlines
Deal found 11/4$240
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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.
Mon 11/2411:24 amSJO - ORD
1 stop11h 42mSpirit Airlines
Sun 12/75:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Deal found 11/4$241
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Fri 12/51:31 pmSJO - ORD
1 stop30h 30mSpirit Airlines
Tue 12/95:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Deal found 11/4$251
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Mon 12/81:31 pmSJO - ORD
1 stop21h 37mMultiple Airlines
Thu 12/116:15 amORD - SJO
1 stop30h 10mMultiple Airlines
Deal found 11/3$252
This OneTravel deal was found by Cheapflights users on 11/4. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/51:31 pmSJO - ORD
1 stop21h 37mSpirit Airlines
Mon 12/85:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Deal found 11/4$253
This eDestinos deal was found by Cheapflights users on 11/5. 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.
Fri 11/1412:34 pmSJO - ORD
2 stops11h 53mSpirit Airlines
Tue 11/254:58 pmORD - SJO
1 stop17h 21mSpirit Airlines
Deal found 11/5$254
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/41:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Wed 12/103:26 pmORD - SJO
1 stop20h 59mSpirit Airlines
Deal found 11/4$255
This Cheapflightsfares deal was found by Cheapflights users on 11/6. 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 11/2211:24 amSJO - ORD
1 stop11h 42mSpirit Airlines
Fri 12/55:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Deal found 11/6$258
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Fri 12/51:31 pmSJO - ORD
1 stop30h 30mSpirit Airlines
Thu 12/111:52 pmORD - SJO
2 stops21h 50mSpirit Airlines
Deal found 11/4$259

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 November 6, 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

Tue 11/25

7:00 am-6:52 pm

1 stop11h 52m

Chicago O'Hare Intl

Sun 11/30

6:45 am-10:07 pm

1 stop15h 22m

$339

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 12/4

7:00 am-6:27 pm

2 stops11h 27m

Chicago O'Hare Intl

Tue 12/9

6:45 am-10:20 pm

2 stops15h 35m

$339

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 12/3

7:00 am-8:35 pm

2 stops13h 35m

Chicago O'Hare Intl

Wed 12/10

10:45 am-10:20 pm

2 stops11h 35m

$339

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Mon 11/24

7:00 am-4:46 pm

1 stop9h 46m

Chicago O'Hare Intl

Sun 11/30

6:45 am-10:07 pm

1 stop15h 22m

$339

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 12/3

7:00 am-3:20 pm

1 stop8h 20m

Chicago O'Hare Intl

Tue 12/9

6:45 am-10:20 pm

2 stops15h 35m

$339

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 12/2

7:00 am-6:43 pm

1 stop11h 43m

Chicago O'Hare Intl

Wed 12/10

6:45 am-10:20 pm

1 stop15h 35m

$339

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 12/25

7:00 am-8:36 pm

2 stops13h 36m

Chicago O'Hare Intl

Wed 12/31

10:46 am-9:55 pm

1 stop11h 09m

$339

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/17

7:00 am-4:31 pm

1 stop9h 31m

Chicago Midway

Sat 1/24

10:46 am-10:15 pm

1 stop11h 29m

$343

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 1/17

7:00 am-9:04 pm

2 stops14h 04m

Chicago O'Hare Intl

Sun 1/25

7:05 am-10:15 pm

1 stop15h 10m

$343

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 11/19

7:45 am-10:35 am

1 stop26h 50m

Chicago O'Hare Intl

Sun 11/23

11:40 am-3:30 pm

1 stop27h 50m

$345

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 54 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, October is the cheapest month in which you can book a flight from Costa Rica to Chicago (average of $198). Flying from Costa Rica to Chicago in March is currently the most expensive (average of $351). 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 November 6, 2025.

It’s typically best to fly out from Costa Rica to Chicago in the evening. Doing so could potentially save you 31% on the flight price compared to flying at noon, 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 Sunday afternoons when fares are most often at their lowest. Wednesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Costa Rica to Chicago

Explore weekly flight availability from Costa Rica to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 6, 2025.

The most flights from CR0 to CHI are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 November 6, 2025.
Read reviews from past customers who have flown Southwest, Copa Airlines, and United Airlines from Costa Rica to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Copa Airlines
7.6
Good
1,563 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,007 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,040 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,122 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Costa Rica to Chicago?

    A quick flight from Costa Rica to Chicago can take about 11h 52m. Delta provides one of the quickest options available for as low as $339. The distance between Costa Rica and Chicago is about 2220 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Costa Rica to Chicago one-way?

    $143 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 $167 and $173, 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 $351, our data shows the cheapest flight currently is $145. When looking at the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl), you can expect to pay $221 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, October is the cheapest month in which you can book a flight from Costa Rica to Chicago (average of $198). Flying from Costa Rica to Chicago in March is currently the most expensive (average of $351). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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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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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$230Average$398FlexibilityNo cancel feeOn-time65%
AviancaCheapest$249Average$485FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$314Average$458FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$324Average$463FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$425Average$525FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$434Average$659FlexibilityNo cancel feeOn-time69%

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