HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$132+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — CHI
apr 5 — apr 121
lör 4/5
lör 4/12
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 mars 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$300
(Mytrip)

One-way from

$132
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$467

Good round-trip deal

$533 or less

Good one-way deal

$235 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 ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 mars 31, 2025.

This Mytrip deal was found by Cheapflights users on 3/31. 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.
tis 4/2912:55 amSJO - ORD
1 stop22h 25mSpirit Airlines
sön 5/47:33 pmORD - SJO
1 stop16h 45mSpirit Airlines
Deal found 3/31$300
This CheapOair deal was found by Cheapflights users on 3/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mån 8/182:48 pmSJO - ORD
1 stop13h 54mMultiple Airlines
lör 9/61:40 amORD - SJO
1 stop13h 17mMultiple Airlines
Deal found 3/31$303
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tis 7/221:55 amSJO - ORD
1 stop10h 20mAvianca
sön 7/273:45 pmORD - SJO
2 stops8h 50mAvianca
Deal found 3/31$341
This United Airlines deal was found by Cheapflights users on 3/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons 6/257:55 amSJO - ORD
1 stop15h 18mUnited Airlines
sön 7/69:50 pmORD - SJO
1 stop25h 49mUnited Airlines
Deal found 3/31$389
This Air Canada deal was found by Cheapflights users on 3/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fre 4/113:05 pmLIR - ORD
1 stop18h 42mAir Canada
sön 4/278:25 pmORD - LIR
1 stop17h 45mAir Canada
Deal found 3/30$419
This Delta deal was found by Cheapflights users on 3/31. 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.
tors 4/37:00 amSJO - MDW
2 stops10h 02mDelta
sön 4/612:48 pmMDW - SJO
1 stop9h 38mDelta
Deal found 3/31$435
This Delta deal was found by Cheapflights users on 3/31. 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.
tors 4/37:00 amSJO - ORD
2 stops12h 45mDelta
sön 4/65:45 amORD - SJO
1 stop7h 09mDelta
Deal found 3/31$435
This Southwest deal was found by Cheapflights users on 3/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tors 8/141:40 pmSJO - MDW
1 stop9h 25mSouthwest
sön 8/178:10 amMDW - SJO
2 stops11h 55mSouthwest
Deal found 3/31$441
This American Airlines deal was found by Cheapflights users on 3/31. 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.
lör 5/1712:30 pmSJO - ORD
2 stops10h 41mAmerican Airlines
ons 5/218:22 amORD - SJO
2 stops11h 13mAmerican Airlines
Deal found 3/31$448
This Copa Airlines deal was found by Cheapflights users on 3/31. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lör 7/510:57 amSJO - ORD
1 stop12h 23mCopa Airlines
tors 7/103:07 pmORD - SJO
1 stop17h 28mCopa Airlines
Deal found 3/31$451
This Mytrip deal was found by Cheapflights users on 3/30. 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.
tors 6/1212:28 pmSJO - MDW
2 stops30h 18mMultiple Airlines
mån 7/1410:31 amMDW - SJO
2 stops29h 42mMultiple Airlines
Deal found 3/30$453
This CheapOair deal was found by Cheapflights users on 3/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lör 6/141:47 pmSJO - MDW
1 stop8h 35mFrontier
lör 6/216:00 amMDW - SJO
1 stop7h 37mFrontier
Deal found 3/31$489

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 mars 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

tis 4/29

12:55 am-12:20 am

1 stop22h 25m

Chicago O'Hare Intl

sön 5/4

7:33 pm-11:18 am

1 stop16h 45m

$300

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

mån 8/18

2:48 pm-5:42 am

1 stop13h 54m

Chicago O'Hare Intl

lör 9/6

1:40 am-1:57 pm

1 stop13h 17m

$303

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

tis 7/22

1:55 am-1:15 pm

1 stop10h 20m

Chicago O'Hare Intl

sön 7/27

3:45 pm-11:35 pm

2 stops8h 50m

$341

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

ons 6/25

7:55 am-12:13 am

1 stop15h 18m

Chicago O'Hare Intl

sön 7/6

9:50 pm-10:39 pm

1 stop25h 49m

$389

LiberiaChicago

LIR - ORD

LIRORD

Liberia

fre 4/11

3:05 pm-10:47 am

1 stop18h 42m

Chicago O'Hare Intl

sön 4/27

8:25 pm-1:10 pm

1 stop17h 45m

$419

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

tors 8/14

1:40 pm-12:05 am

1 stop9h 25m

Chicago Midway

sön 8/17

8:10 am-7:05 pm

2 stops11h 55m

$441

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

lör 5/17

12:30 pm-12:11 am

2 stops10h 41m

Chicago O'Hare Intl

ons 5/21

8:22 am-6:35 pm

2 stops11h 13m

$448

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

lör 7/5

10:05 am-12:20 am

1 stop13h 15m

Chicago O'Hare Intl

lör 7/19

3:07 pm-7:35 am

1 stop17h 28m

$451

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

tors 6/12

12:28 pm-7:46 pm

2 stops30h 18m

Chicago Midway

mån 7/14

10:31 am-3:13 pm

2 stops29h 42m

$453

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

lör 6/14

1:47 pm-11:22 pm

1 stop8h 35m

Chicago Midway

lör 6/21

6:00 am-12:37 pm

1 stop7h 37m

$489

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 36 results
1
2
3
4

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 $323). 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 mars 31, 2025.

It’s typically best to fly out from Costa Rica to Chicago at noon. Doing so could potentially save you 11% on the flight price compared to flying in the morning, 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. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 mars 31, 2025.
Read through reviews of airlines operating flights from Costa Rica to Chicago, such as Alaska Airlines, Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,818 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,818 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,277 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,899 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Copa Airlines
7.6
Good
1,400 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Aeromexico
7.5
Good
1,700 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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?

    $132 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 $183 and $208, 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 $530, our data shows the cheapest flight currently is $146. When looking at the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl), you can expect to pay $238 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 $323). 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 Costa Rica?

Book flights to Costa Rica if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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.
Guatemala City to O'Hare Intl flights
San José to O'Hare Intl flights
San Salvador to O'Hare Intl flights
Guatemala City to Midway flights
Panama City to O'Hare Intl flights
San José to Midway flights
San José to St. Louis flights
San Pedro Sula to O'Hare Intl flights
Managua to O'Hare Intl flights
Philip S.W.Goldson to O'Hare Intl flights
San Pedro Sula to Midway flights
Panama City to St. Louis flights
Liberia to O'Hare Intl flights
Philip S.W.Goldson to Midway flights
Guatemala City to St. Louis flights
Coxen Hole to O'Hare Intl flights
Managua to Midway flights
Managua to St. Louis flights
San Pedro Sula to St. Louis flights
Tegucigalpa 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 mars 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$202Average$386FlexibilityNo cancel feeOn-time65%
AviancaCheapest$290Average$470FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$326Average$560FlexibilityNo cancel feeOn-time70%
DeltaCheapest$434Average$649FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$438Average$732FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$480Average$600FlexibilityNo 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.