HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$107+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Costa Rica to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 16, 2025.

Round-trip from

$184
(Cheapflightsfares)

One-way from

$107
(Cheapflightsfares)

Popular in

June

Cheapest in

November

Average price

$446

Good round-trip deal

$395 or less

Good one-way deal

$194 or less
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. 3% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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

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 September 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Wed 10/812:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Tue 10/145:05 amORD - SJO
1 stop7h 25mSpirit Airlines
Deal found 9/15$184
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Wed 10/112:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Sat 10/117:43 pmORD - SJO
1 stop16h 47mSpirit Airlines
Deal found 9/15$187
This eDestinos deal was found by Cheapflights users on 9/14. 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.
Thu 9/2512:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Thu 10/26:44 pmORD - SJO
1 stop17h 30mSpirit Airlines
Deal found 9/14$192
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Wed 10/812:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Thu 10/167:43 pmORD - SJO
1 stop16h 47mSpirit Airlines
Deal found 9/14$195
This Priceline deal was found by Cheapflights users on 9/15. 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.
Wed 10/812:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Sat 10/187:43 pmORD - SJO
1 stop16h 47mSpirit Airlines
Deal found 9/15$198
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2312:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Tue 9/305:05 amORD - SJO
1 stop7h 09mSpirit Airlines
Deal found 9/16$199
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Fri 10/312:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Fri 10/107:43 pmORD - SJO
1 stop16h 47mSpirit Airlines
Deal found 9/14$200
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/212:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Thu 10/97:43 pmORD - SJO
1 stop16h 47mSpirit Airlines
Deal found 9/14$202
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Fri 10/1012:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Sat 10/187:43 pmORD - SJO
1 stop16h 47mSpirit Airlines
Deal found 9/14$204
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Wed 10/112:19 pmSJO - ORD
1 stop9h 29mSpirit Airlines
Tue 10/77:43 pmORD - SJO
1 stop16h 47mSpirit Airlines
Deal found 9/15$207
This Delta deal was found by Cheapflights users on 9/15. 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.
Thu 10/231:25 pmLIR - ORD
2 stops17h 25mDelta
Tue 10/285:20 amORD - LIR
1 stop7h 20mDelta
Deal found 9/15$294
This Air Canada deal was found by Cheapflights users on 9/16. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/112:55 pmLIR - ORD
1 stop24h 00mAir Canada
Mon 11/1712:50 pmORD - LIR
1 stop25h 05mAir Canada
Deal found 9/16$309

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 September 16, 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

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Thu 10/23

1:25 pm-12:45 pm

2 stops22h 20m

Chicago O'Hare Intl

Wed 10/29

5:20 am-11:40 am

1 stop7h 20m

$294

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Fri 10/24

1:25 pm-9:12 am

2 stops18h 47m

Chicago O'Hare Intl

Wed 10/29

5:20 am-11:40 am

1 stop7h 20m

$294

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Thu 10/23

1:25 pm-12:45 pm

2 stops22h 20m

Chicago O'Hare Intl

Tue 10/28

4:56 pm-11:40 am

2 stops19h 44m

$294

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Fri 10/24

1:25 pm-9:12 am

2 stops18h 47m

Chicago O'Hare Intl

Tue 10/28

4:56 pm-11:40 am

2 stops19h 44m

$294

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Mon 10/27

7:35 am-11:10 pm

1 stop14h 35m

Chicago O'Hare Intl

Wed 10/29

7:10 am-3:08 pm

1 stop8h 58m

$315

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Tue 10/28

11:50 am-11:59 pm

1 stop11h 09m

Chicago O'Hare Intl

Fri 10/31

6:00 am-12:10 pm

1 stop7h 10m

$315

LiberiaChicago

LIR - ORD

LIRORD

Liberia

Sat 10/25

1:25 pm-11:58 pm

1 stop9h 33m

Chicago O'Hare Intl

Wed 10/29

5:20 am-11:40 am

1 stop7h 20m

$315

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 10/1

10:58 am-12:21 am

1 stop12h 23m

Chicago O'Hare Intl

Fri 10/17

3:07 pm-8:19 am

1 stop18h 12m

$323

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Mon 12/1

6:07 pm-12:52 pm

1 stop18h 45m

Chicago O'Hare Intl

Mon 12/8

2:07 pm-7:10 am

1 stop17h 03m

$327

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 10/2

10:08 am-12:21 am

1 stop13h 13m

Chicago O'Hare Intl

Thu 10/9

3:07 pm-4:52 pm

3 stops26h 45m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 56 results
1
2
3
...
6

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 September 16, 2025.

It’s typically best to fly out from Costa Rica to Chicago in the morning. Doing so could potentially save you 20% 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 Tuesday at noon when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 September 16, 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
4,242 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

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
1,531 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

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
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

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
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

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
8,019 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

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 9h 35m. Delta provides one of the quickest options available for as low as $335. 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?

    $140 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 Air Canada, with prices starting from $183 and $213, 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 $328, our data shows the cheapest flight currently is $132. When looking at the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl), you can expect to pay $184 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 Chicago?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Costa Rica to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Guatemala City to O'Hare Intl flights
San José to O'Hare Intl flights
Guatemala City to Midway flights
San Salvador to O'Hare Intl flights
San José to Midway flights
Panama City to O'Hare Intl flights
Managua to O'Hare Intl flights
San Pedro Sula to O'Hare Intl flights
Liberia to O'Hare Intl flights
San Pedro Sula to Midway flights
San José to St. Louis flights
Guatemala City to St. Louis flights
Philip S.W.Goldson to O'Hare Intl flights
Panama City to St. Louis flights
Managua to Midway flights
Philip S.W.Goldson to Midway flights
San Pedro Sula to St. Louis flights
Coxen Hole to O'Hare Intl flights
Tegucigalpa to St. Louis flights
Managua to St. Louis flights
Tegucigalpa to O'Hare Intl flights
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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
AviancaCheapest$249Average$485FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$264Average$417FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$314Average$478FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$377Average$560FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$425Average$527FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$436Average$633FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.