HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$124+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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 julio 31, 2025.

Round-trip from

$266
(FlightHub)

One-way from

$124
(FlightHub)

Popular in

December

Cheapest in

August

Average price

$467

Good round-trip deal

$446 or less

Good one-way deal

$253 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. 2% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 julio 31, 2025.

This Mytrip deal was found by Cheapflights users on 7/31. 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.
lun. 9/227:30 amSJO - ORD
1 stop13h 28mMultiple Airlines
sáb. 9/2711:37 amORD - SJO
2 stops24h 37mMultiple Airlines
Deal found 7/31$265
This FlightHub deal was found by Cheapflights users on 7/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/411:37 amSJO - ORD
1 stop9h 21mSpirit Airlines
sáb. 9/611:57 amORD - SJO
2 stops23h 30mSpirit Airlines
Deal found 7/31$266
This Mytrip deal was found by Cheapflights users on 7/31. 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.
sáb. 8/91:47 pmSJO - MDW
1 stop23h 00mFrontier
sáb. 12/66:00 amMDW - SJO
1 stop7h 32mFrontier
Deal found 7/31$351
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/241:40 pmSJO - MDW
1 stop8h 40mSouthwest
mar. 9/306:25 amMDW - SJO
1 stop13h 30mSouthwest
Deal found 7/29$384
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/151:20 pmLIR - ORD
1 stop9h 54mUnited Airlines
vie. 10/179:44 pmORD - LIR
1 stop18h 41mUnited Airlines
Deal found 7/28$387
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/1111:37 amSJO - MDW
3 stops28h 06mMultiple Airlines
lun. 9/1512:50 pmMDW - SJO
3 stops22h 37mMultiple Airlines
Deal found 7/29$414
This American Airlines deal was found by Cheapflights users on 7/31. 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.
vie. 9/52:02 pmLIR - ORD
1 stop18h 45mAmerican Airlines
dom. 9/147:25 pmORD - LIR
1 stop17h 24mAmerican Airlines
Deal found 7/31$475
This Delta deal was found by Cheapflights users on 7/31. 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.
jue. 9/41:25 pmLIR - ORD
2 stops19h 55mDelta
dom. 9/147:59 pmORD - LIR
1 stop17h 01mDelta
Deal found 7/31$477
This Alaska Airlines deal was found by Cheapflights users on 7/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/211:20 amLIR - ORD
2 stops16h 40mAlaska Airlines
jue. 10/306:00 amORD - LIR
2 stops25h 20mAlaska Airlines
Deal found 7/30$496
This Mytrip deal was found by Cheapflights users on 7/30. 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.
vie. 8/226:50 amLIR - ORD
2 stops14h 32mMultiple Airlines
mar. 8/268:25 pmORD - LIR
1 stop16h 59mMultiple Airlines
Deal found 7/30$614

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 julio 31, 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

lun. 9/22

7:30 am-9:58 pm

1 stop13h 28m

Chicago O'Hare Intl

sáb. 9/27

11:37 am-11:14 am

2 stops24h 37m

$265

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

jue. 9/4

11:37 am-9:58 pm

1 stop9h 21m

Chicago O'Hare Intl

sáb. 9/6

11:57 am-10:27 am

2 stops23h 30m

$266

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

sáb. 8/9

1:47 pm-1:47 pm

1 stop23h 00m

Chicago Midway

sáb. 12/6

6:00 am-1:32 pm

1 stop7h 32m

$351

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

mié. 9/24

1:40 pm-11:20 pm

1 stop8h 40m

Chicago Midway

mar. 9/30

6:25 am-6:55 pm

1 stop13h 30m

$384

LiberiaChicago

LIR - ORD

LIRORD

Liberia

mié. 10/15

1:20 pm-12:14 am

1 stop9h 54m

Chicago O'Hare Intl

vie. 10/17

9:44 pm-3:25 pm

1 stop18h 41m

$387

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

jue. 9/11

11:37 am-4:43 pm

3 stops28h 06m

Chicago Midway

lun. 9/15

12:50 pm-10:27 am

3 stops22h 37m

$414

LiberiaChicago

LIR - ORD

LIRORD

Liberia

vie. 9/5

2:02 pm-9:47 am

1 stop18h 45m

Chicago O'Hare Intl

dom. 9/14

7:25 pm-11:49 am

1 stop17h 24m

$475

LiberiaChicago

LIR - ORD

LIRORD

Liberia

jue. 9/4

1:25 pm-10:20 am

2 stops19h 55m

Chicago O'Hare Intl

dom. 9/14

7:59 pm-12:00 pm

1 stop17h 01m

$477

LiberiaChicago

LIR - ORD

LIRORD

Liberia

jue. 10/2

11:20 am-5:00 am

2 stops16h 40m

Chicago O'Hare Intl

jue. 10/30

6:00 am-6:20 am

2 stops25h 20m

$496

LiberiaChicago

LIR - ORD

LIRORD

Liberia

vie. 8/22

6:50 am-10:22 pm

2 stops14h 32m

Chicago O'Hare Intl

mar. 8/26

8:25 pm-12:24 pm

1 stop16h 59m

$614

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 22 results
1
2
3

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 julio 31, 2025.

It’s typically best to fly out from Costa Rica to Chicago in the morning. Doing so could potentially save you 10% 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 julio 31, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and Delta 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
United Airlines
7.4
Good
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave

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?

    $124 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 Frontier and Delta, with prices starting from $180 and $202, 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 $435, our data shows the cheapest flight currently is $232. When looking at the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl), you can expect to pay $234 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
Valparaiso
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.
San José to O'Hare Intl flights
Guatemala City to O'Hare Intl flights
San José to Midway flights
Guatemala City to Midway flights
San Salvador to O'Hare Intl flights
Panama City to O'Hare Intl flights
San Pedro Sula to O'Hare Intl flights
San José to St. Louis flights
Guatemala City to St. Louis flights
San Pedro Sula to Midway flights
Philip S.W.Goldson to O'Hare Intl flights
Panama City to St. Louis flights
Philip S.W.Goldson to Midway flights
Managua to O'Hare Intl flights
San Pedro Sula to St. Louis flights
Liberia to O'Hare Intl flights
Coxen Hole to O'Hare Intl flights
Tegucigalpa to O'Hare Intl flights
Managua to Midway flights
Managua to St. Louis flights
Tegucigalpa to St. Louis 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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
AviancaCheapest$261Average$462FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$266Average$414FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$314Average$486FlexibilityNo cancel feeOn-time70%
SouthwestCheapest$425Average$527FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$436Average$630FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$446Average$566FlexibilityNo cancel feeOn-time71%

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.