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$170+ 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 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Apr 23 — Apr 301
Thu 4/23
Thu 4/30
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 March 24, 2026.

This CheapOair deal was found by Cheapflights users on 3/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/812:19 pm
SJO
-
ORD
1 stop21h 58m
Spirit Airlines
Sun 4/125:05 am
ORD
-
SJO
1 stop7h 09m
Spirit Airlines
Deal found 3/21$331
This CheapOair deal was found by Cheapflights users on 3/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1412:19 pm
SJO
-
ORD
1 stop20h 17m
Spirit Airlines
Sun 4/195:05 am
ORD
-
SJO
1 stop7h 28m
Spirit Airlines
Deal found 3/21$332
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 5/412:38 pm
SJO
-
ORD
1 stop10h 49m
Multiple Airlines
Sat 5/94:05 pm
ORD
-
SJO
2 stops20h 28m
Multiple Airlines
Deal found 3/19$334
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 5/312:38 pm
SJO
-
ORD
1 stop19h 53m
Multiple Airlines
Sat 5/94:05 pm
ORD
-
SJO
2 stops20h 28m
Multiple Airlines
Deal found 3/19$335
This Cheapflightsfares deal was found by Cheapflights users on 3/22. 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 4/912:19 pm
SJO
-
ORD
1 stop9h 58m
Spirit Airlines
Sun 4/126:10 pm
ORD
-
SJO
1 stop18h 04m
Spirit Airlines
Deal found 3/22$336
This CheapOair deal was found by Cheapflights users on 3/23. 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 4/2412:38 pm
SJO
-
ORD
1 stop10h 46m
Spirit Airlines
Wed 4/296:16 pm
ORD
-
SJO
2 stops18h 17m
Spirit Airlines
Deal found 3/23$337
This OneTravel deal was found by Cheapflights users on 3/21. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/712:19 pm
SJO
-
ORD
1 stop21h 58m
Spirit Airlines
Sat 4/187:15 pm
ORD
-
SJO
1 stop17h 18m
Spirit Airlines
Deal found 3/21$338
This CheapOair deal was found by Cheapflights users on 3/23. 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.
Mon 4/1312:19 pm
SJO
-
ORD
1 stop27h 56m
Spirit Airlines
Mon 4/205:05 am
ORD
-
SJO
1 stop7h 28m
Spirit Airlines
Deal found 3/23$339
This Cheapflightsfares deal was found by Cheapflights users on 3/23. 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 4/1612:38 pm
SJO
-
ORD
2 stops9h 29m
Spirit Airlines
Mon 4/205:05 am
ORD
-
SJO
1 stop7h 28m
Spirit Airlines
Deal found 3/23$340
This CheapOair deal was found by Cheapflights users on 3/23. 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.
Thu 4/1612:38 pm
SJO
-
ORD
1 stop10h 46m
Spirit Airlines
Thu 4/2311:28 am
ORD
-
SJO
2 stops25h 05m
Spirit Airlines
Deal found 3/23$341
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 5/412:38 pm
SJO
-
ORD
1 stop10h 49m
Spirit Airlines
Thu 5/147:45 pm
ORD
-
SJO
1 stop16h 48m
Spirit Airlines
Deal found 3/19$342
This CheapOair deal was found by Cheapflights users on 3/23. 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.
Thu 4/21:27 pm
SJO
-
MDW
1 stop29h 40m
Frontier
Fri 4/105:30 am
MDW
-
SJO
1 stop28h 31m
Frontier
Deal found 3/23$350

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 March 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$331
(CheapOair)

One-way from

$170
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$515

Good round-trip deal

$159 or less

Good one-way deal

$225 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. 5% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 24, 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

Wed 6/3

8:47 am-4:00 am

1 stop18h 13m

Chicago O'Hare Intl

Thu 6/11

3:21 pm-8:21 am

1 stop18h 00m

$473

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 4/22

4:09 am-1:50 pm

1 stop8h 41m

Chicago O'Hare Intl

Mon 4/27

3:05 pm-8:20 am

1 stop18h 15m

$473

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 6/2

4:10 am-2:06 pm

1 stop8h 56m

Chicago O'Hare Intl

Thu 6/11

3:21 pm-8:21 am

1 stop18h 00m

$473

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 6/2

5:57 pm-4:00 am

1 stop9h 03m

Chicago O'Hare Intl

Sat 6/13

3:21 pm-7:12 am

1 stop16h 51m

$473

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 5/16

2:50 pm-1:15 am

1 stop9h 25m

Chicago O'Hare Intl

Sat 5/30

3:21 pm-8:21 am

1 stop18h 00m

$473

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 5/27

2:59 pm-1:15 am

1 stop9h 16m

Chicago O'Hare Intl

Wed 6/3

3:21 pm-9:06 am

1 stop18h 45m

$473

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 5/27

2:21 pm-1:15 am

1 stop9h 54m

Chicago O'Hare Intl

Mon 6/1

3:21 pm-7:12 am

1 stop16h 51m

$473

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Tue 5/5

5:50 am-1:15 am

1 stop18h 25m

Chicago O'Hare Intl

Sat 5/9

3:21 pm-7:09 am

1 stop16h 48m

$473

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 5/9

1:35 pm-10:45 pm

1 stop8h 10m

Chicago Midway

Wed 5/13

12:15 pm-7:00 pm

1 stop7h 45m

$480

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 5/5

1:21 pm-10:28 pm

1 stop8h 07m

Chicago Midway

Sat 5/9

6:23 am-1:15 pm

1 stop7h 52m

$511

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/22

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

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

Currently, May is the cheapest month in which you can book a flight from Costa Rica to Chicago (average of $188). Flying from Costa Rica to Chicago in March is currently the most expensive (average of $338). 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 March 24, 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.

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 March 24, 2026.

The most flights from CR0 to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

How often are flights from Costa Rica to Chicago delayed?

About 10% of weekly flights between Costa Rica and Chicago have experienced delays in the past year, with the average delay time being 191 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 Monday 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 March 24, 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
4,324 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

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
4,324 reviews
Southwest
8.0
Very good
4,324 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

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
1,575 reviews
Southwest
8.0
Very good
4,324 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

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
9,463 reviews
Southwest
8.0
Very good
4,324 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

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
11,486 reviews
Southwest
8.0
Very good
4,324 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

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
8,539 reviews
Southwest
8.0
Very good
4,324 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

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 8h 07m. Copa Airlines provides one of the quickest options available for as low as $511. 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?

    $179 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 $469, our data shows the cheapest flight currently is $180. When looking at the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl), you can expect to pay $305 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, May is the cheapest month in which you can book a flight from Costa Rica to Chicago (average of $188). Flying from Costa Rica to Chicago in March is currently the most expensive (average of $338). 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
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Hammond
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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 March 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$179Average$298FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$189Average$443FlexibilityNo cancel feeOn-time70%
AviancaCheapest$261Average$484FlexibilityNo cancel feeOn-time71%
American AirlinesCheapest$337Average$470FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$400Average$483FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$463Average$507FlexibilityNo cancel feeOn-time63%

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