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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 7/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Jun 8 — Jun 151
Mon 6/8
Mon 6/15
1 adult, Economy
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Cheap 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 9, 2026.

This CheapOair deal was found by Cheapflights users on 5/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/229:35 am
SJO
-
ORD
1 stop12h 39m
Multiple Airlines
Sat 8/297:00 am
ORD
-
SJO
1 stop6h 57m
Multiple Airlines
Deal found 5/9$361
This Expedia deal was found by Cheapflights users on 5/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/259:35 am
SJO
-
ORD
1 stop12h 30m
Frontier
Sat 8/15:13 pm
ORD
-
SJO
1 stop16h 07m
Frontier
Deal found 5/6$364
This CheapOair deal was found by Cheapflights users on 5/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:35 am
SJO
-
ORD
1 stop12h 39m
Frontier
Wed 8/265:30 pm
ORD
-
SJO
1 stop15h 50m
Frontier
Deal found 5/9$365
This CheapOair deal was found by Cheapflights users on 5/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/159:35 am
SJO
-
ORD
1 stop12h 30m
Multiple Airlines
Wed 8/197:00 am
ORD
-
SJO
1 stop6h 57m
Multiple Airlines
Deal found 5/8$366
This Copa Airlines deal was found by Cheapflights users on 5/4. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/186:19 pm
SJO
-
ORD
1 stop22h 07m
Copa Airlines
Sun 6/211:00 am
ORD
-
SJO
1 stop11h 06m
Copa Airlines
Deal found 5/4$368
This Expedia deal was found by Cheapflights users on 5/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/229:35 am
SJO
-
ORD
1 stop12h 39m
Frontier
Sat 9/55:30 pm
ORD
-
SJO
1 stop15h 50m
Frontier
Deal found 5/8$370
This United Airlines deal was found by Cheapflights users on 5/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2512:30 am
SJO
-
ORD
1 stop9h 31m
United Airlines
Wed 6/106:30 am
ORD
-
SJO
1 stop14h 07m
United Airlines
Deal found 5/4$371
This American Airlines deal was found by Cheapflights users on 5/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/281:29 pm
SJO
-
ORD
1 stop18h 42m
American Airlines
Sun 9/65:15 am
ORD
-
SJO
1 stop8h 11m
American Airlines
Deal found 5/4$380
This American Airlines deal was found by Cheapflights users on 5/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/211:29 pm
SJO
-
ORD
1 stop9h 28m
American Airlines
Mon 8/317:30 am
ORD
-
SJO
2 stops13h 22m
American Airlines
Deal found 5/5$384
This CheapOair deal was found by Cheapflights users on 5/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/159:35 am
SJO
-
ORD
1 stop12h 30m
Frontier
Wed 8/195:30 pm
ORD
-
SJO
1 stop15h 50m
Frontier
Deal found 5/6$386
This American Airlines deal was found by Cheapflights users on 5/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:29 pm
SJO
-
ORD
1 stop9h 30m
American Airlines
Tue 9/15:01 am
ORD
-
SJO
1 stop15h 51m
American Airlines
Deal found 5/4$387
This American Airlines deal was found by Cheapflights users on 5/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/272:45 pm
SJO
-
ORD
1 stop19h 18m
American Airlines
Sat 10/316:26 pm
ORD
-
SJO
1 stop18h 56m
American Airlines
Deal found 5/5$389

Find 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 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$361
(CheapOair)

One-way from

$198
(Priceline)

Popular in

March

Cheapest in

January

Average price

$488

Good round-trip deal

$494 or less

Good one-way deal

$202 or less
Provider with most accurate pricing for San José Juan Santamaria Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-Chicago (CHI) flights.
Search Deals
From Costa Rica to Chicago (CHI)
Search Deals
One-way flight from Costa Rica to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Costa Rica to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Costa Rica to Chicago (CHI).
Search Deals

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 9, 2026.
Use the filters below to find and compare flights from Costa Rica to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sun 5/24

6:00 am-7:05 pm

1 stop12h 05m

Chicago O'Hare Intl

Mon 6/8

7:30 am-10:39 pm

1 stop16h 09m

$469

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 7/15

5:55 pm-1:57 pm

1 stop19h 02m

Chicago O'Hare Intl

Thu 7/30

3:21 pm-7:12 am

1 stop16h 51m

$473

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 7/15

4:08 am-1:57 pm

1 stop8h 49m

Chicago O'Hare Intl

Tue 7/21

3:21 pm-7:12 am

1 stop16h 51m

$473

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 5/19

1:25 pm-11:15 pm

1 stop8h 50m

Chicago O'Hare Intl

Thu 6/4

5:30 am-10:39 pm

1 stop18h 09m

$500

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 5/15

7:55 am-1:27 am

1 stop16h 32m

Chicago O'Hare Intl

Sat 6/13

5:30 am-10:39 pm

1 stop18h 09m

$500

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 7/1

10:03 am-4:00 am

1 stop16h 57m

Chicago O'Hare Intl

Tue 7/7

8:02 am-7:01 pm

1 stop11h 59m

$521

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 5/26

12:30 am-2:51 pm

1 stop13h 21m

Chicago O'Hare Intl

Thu 6/18

9:36 pm-7:37 pm

1 stop23h 01m

$521

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sun 5/31

7:55 am-12:45 am

1 stop15h 50m

Chicago O'Hare Intl

Sat 6/6

5:30 am-10:39 pm

1 stop18h 09m

$530

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 5/23

1:00 pm-7:35 pm

Nonstop5h 35m

Chicago O'Hare Intl

Sat 5/30

6:00 am-9:15 pm

1 stop16h 15m

$544

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 6/17

12:08 pm-4:00 am

1 stop14h 52m

Chicago O'Hare Intl

Sun 6/21

3:21 pm-7:09 am

1 stop16h 48m

$548

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/8

Showing 1-10 of 60 resultsSorted by cheapest first
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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

How far ahead should I book a flight from Costa Rica to Chicago?

Booking 29 days in advance of your planned departure date is, on average, the best time to get cheap flights from Costa Rica to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, November is the cheapest month in which you can book a flight from Costa Rica to Chicago (average of $111). Flying from Costa Rica to Chicago in December is currently the most expensive (average of $194). 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 9, 2026.

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.

How often are flights from Costa Rica to Chicago delayed?

About 9% of weekly flights between Costa Rica and Chicago have experienced delays in the past year, with the average delay time being 192 minutes.

What is the most punctual flight time for Costa Rica to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Costa Rica to Chicago flights?

Over the last year, American Airlines have had the lowest number of delays on this route, with just 7% of flights being delayed.

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 9, 2026.
Read reviews from past customers who have flown Southwest,Copa Airlines, andUnited 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
4,303 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,303 reviews
Southwest
8.0
Very good
4,303 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Copa Airlines
7.5
Good
1,584 reviews
Southwest
8.0
Very good
4,303 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,695 reviews
Southwest
8.0
Very good
4,303 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,668 reviews
Southwest
8.0
Very good
4,303 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.3
Okay
8,634 reviews
Southwest
8.0
Very good
4,303 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 10h 45m. United Airlines provides one of the quickest options available for as low as $598. The distance between Costa Rica and Chicago is about 2206 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?

    $172 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 American Airlines and Copa Airlines, with prices starting from $183 and $198, 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 $374, our data shows the cheapest flight currently is $177. When looking at the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl), you can expect to pay $366 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, November is the cheapest month in which you can book a flight from Costa Rica to Chicago (average of $111). Flying from Costa Rica to Chicago in December is currently the most expensive (average of $194). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$179Average$289FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$189Average$458FlexibilityNo cancel feeOn-time70%
AviancaCheapest$249Average$410FlexibilityNo cancel feeOn-time71%
American AirlinesCheapest$332Average$514FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$379Average$472FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$463Average$507FlexibilityNo cancel feeOn-time63%

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