$132+ Cheap flights from Chicago (CHI) to Costa Rica
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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Chicago to Costa Rica 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 Chicago to Costa Rica
Keep the following information in mind while searching for Chicago to Costa Rica flight deals. Data was last updated March 28, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $332 (Kiwi.com) |
One-way from | $132 (Mytrip) |
Popular in | December |
Cheapest in | May |
Average price | $690 |
Good round-trip deal | $635 or less |
Good one-way deal | $245 or less |
Find flight deals from Chicago to Costa Rica
Cheapest flights from Chicago to Costa RicaExplore the most affordable flight options available from Chicago to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 28, 2025.
Explore the most affordable flight options available from Chicago to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 28, 2025.
This Kiwi.com deal was found by Cheapflights users on 3/26. 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.
This Mytrip deal was found by Cheapflights users on 3/27. 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.
This Cheapflightsfares deal was found by Cheapflights users on 3/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
This KAYAK deal was found by Cheapflights users on 3/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This American Airlines deal was found by Cheapflights users on 3/27. 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.
This Delta deal was found by Cheapflights users on 3/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 3/26. 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.
This CheapOair deal was found by Cheapflights users on 3/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 3/27. 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.
This American Airlines deal was found by Cheapflights users on 3/27. 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.
This Southwest deal was found by Cheapflights users on 3/27. 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.
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Costa Rica 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 28, 2025.
Use the filters below to find and compare flights from Chicago to Costa Rica that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sun 5/11
4:15 pm-10:27 am
1 stop19h 12m
San José Juan Santamaria Intl
Sun 5/18
12:28 pm-11:32 pm
2 stops34h 04m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Fri 5/9
7:47 am-10:27 am
1 stop27h 40m
San José Juan Santamaria Intl
Mon 5/12
11:32 am-12:24 am
3 stops35h 52m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Fri 6/6
3:45 pm-9:50 pm
1 stop7h 05m
San José Juan Santamaria Intl
Mon 6/9
7:45 pm-4:05 pm
1 stop19h 20m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Wed 4/9
12:46 pm-10:24 am
1 stop22h 38m
San José Juan Santamaria Intl
Wed 4/16
11:35 am-9:24 am
1 stop20h 49m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sat 6/14
3:07 pm-7:35 am
1 stop17h 28m
San José Juan Santamaria Intl
Sun 6/22
6:07 pm-1:47 pm
1 stop18h 40m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Wed 5/7
5:30 am-11:59 am
1 stop7h 29m
San José Juan Santamaria Intl
Sat 5/24
2:30 pm-11:17 pm
1 stop7h 47m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sat 5/10
8:05 am-10:24 pm
1 stop15h 19m
San José Juan Santamaria Intl
Sat 5/17
6:03 am-11:56 pm
1 stop16h 53m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Wed 5/7
8:40 am-7:40 pm
2 stops12h 00m
San José Juan Santamaria Intl
Wed 5/14
8:45 am-9:05 pm
2 stops11h 20m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 8/2
6:00 am-12:35 pm
1 stop7h 35m
San José Juan Santamaria Intl
Sat 8/9
1:47 pm-11:21 pm
1 stop8h 34m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 4/19
6:04 am-1:28 pm
1 stop8h 24m
San José Juan Santamaria Intl
Sat 4/26
1:20 pm-10:22 pm
1 stop8h 02m
Best time to book a flight from Chicago to Costa Rica
Have a flexible travel schedule? Discover the best time to fly to Costa Rica from Chicago with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Costa Rica
What is the cheapest month to book a flight from Chicago to Costa Rica?
Currently, September is the cheapest month in which you can book a flight from Chicago to Costa Rica (average of $398). Flying from Chicago to Costa Rica in March is currently the most expensive (average of $555). 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 CHI to CR?
Find hourly flight availability from Chicago to Costa Rica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 28, 2025.
When flying from Chicago to Costa Rica, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 48% versus a flight at noon.
What is the cheapest day to fly from Chicago to Costa Rica?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Costa Rica. Price data was last updated on April 7, 2024.
Travelers seeking maximum savings on their Chicago to Costa Rica flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Rainfall in Costa Rica by month
Plan your trip to Costa Rica by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Costa Rica ranges from 0.0 - 11.8 inches per month. September is typically the wettest month, when rainfall can reach 11.8 in. February is typically the driest time to visit Costa Rica when rainfall is around 0.0 in.
Temperature in Costa Rica by month
Plan your trip to Costa Rica by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Costa Rica, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 64.4 F).
Reviews of airlines servicing Costa Rica
Get insights into the airlines that provide service to Costa Rica. 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 Costa Rica. Reviews last updated March 28, 2025.
Get a feel of what it's like to fly with Southwest, Alaska Airlines and Delta from Chicago to Costa Rica by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
Boarding
Overall
Food
Comfort
Entertainment
Reviews
Ila,Mar 2025
HOU - DAL
Crew
Boarding
Overall
Food
Comfort
Entertainment
Reviews
Ila,Mar 2025
HOU - DAL
Crew
Boarding
Overall
Food
Comfort
Entertainment
Reviews
Ila,Mar 2025
HOU - DAL
Crew
Boarding
Overall
Food
Comfort
Entertainment
Reviews
Ila,Mar 2025
HOU - DAL
Crew
Boarding
Overall
Food
Comfort
Entertainment
Reviews
Ila,Mar 2025
HOU - DAL
Crew
Boarding
Overall
Food
Comfort
Entertainment
Reviews
Ila,Mar 2025
HOU - DAL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Costa Rica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Chicago to Costa Rica
See prices for flight routes from nearby airports that may be better suited for you.
Top 8 airlines flying from Chicago to Costa Rica
Discover the top 8 airlines that operate flights from Chicago to Costa Rica. 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 28, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$237 | Average$405 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$337 | Average$475 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$345 | Average$623 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$430 | Average$620 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$447 | Average$802 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$538 | Average$699 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$542 | Average$740 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$569 | Average$837 | FlexibilityNo cancel fee | On-time69% |