$103+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
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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
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 diciembre 4, 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 diciembre 4, 2025.
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 Kiwi.com deal was found by Cheapflights users on 12/2. 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 Kiwi.com deal was found by Cheapflights users on 12/1. 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 FlightHub deal was found by Cheapflights users on 12/2. 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.
This Expedia deal was found by Cheapflights users on 12/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Expedia deal was found by Cheapflights users on 12/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Expedia deal was found by Cheapflights users on 12/2. 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 Expedia 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 12/3. 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 Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/3. 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 Kiwi.com deal was found by Cheapflights users on 12/3. 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.
Find 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 diciembre 4, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $314 (Kiwi.com) |
One-way from | $103 (Cheapflightsfares) |
Popular in | December |
Cheapest in | September |
Average price | $671 |
Good round-trip deal | $463 or less |
Good one-way deal | $176 or less |
Cheapflights Fare Finder
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
sáb. 2/21
6:33 pm-3:30 pm
1 stop20h 57m
San José Juan Santamaria Intl
dom. 3/1
7:45 am-9:16 am
1 stop25h 31m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
lun. 2/2
7:39 am-12:56 pm
Nonstop5h 17m
San José Juan Santamaria Intl
jue. 2/12
2:05 pm-7:35 pm
Nonstop5h 30m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
vie. 2/20
2:22 pm-7:06 am
1 stop16h 44m
San José Juan Santamaria Intl
dom. 3/1
10:08 am-12:04 am
1 stop13h 56m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
mar. 2/3
2:22 pm-7:06 am
1 stop16h 44m
San José Juan Santamaria Intl
mar. 2/10
5:51 pm-12:31 pm
1 stop18h 40m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
jue. 2/26
2:22 pm-8:21 am
1 stop17h 59m
San José Juan Santamaria Intl
vie. 3/6
8:11 am-12:04 am
1 stop15h 53m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
vie. 2/20
10:53 am-10:02 pm
1 stop11h 09m
San José Juan Santamaria Intl
vie. 3/6
7:00 am-10:42 pm
1 stop15h 42m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
sáb. 1/31
10:46 am-10:15 pm
1 stop11h 29m
San José Juan Santamaria Intl
sáb. 2/7
7:00 am-3:38 pm
1 stop8h 38m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
mié. 2/25
6:45 am-10:02 pm
1 stop15h 17m
San José Juan Santamaria Intl
vie. 3/6
7:00 am-8:57 pm
1 stop13h 57m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
sáb. 2/7
7:05 am-10:15 pm
1 stop15h 10m
San José Juan Santamaria Intl
dom. 2/15
7:00 am-7:19 pm
1 stop12h 19m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
jue. 3/5
2:22 pm-7:05 am
1 stop16h 43m
San José Juan Santamaria Intl
vie. 3/13
4:09 am-1:31 pm
1 stop8h 22m
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, October is the cheapest month in which you can book a flight from Chicago to Costa Rica (average of $248). Flying from Chicago to Costa Rica in March is currently the most expensive (average of $367). 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 diciembre 4, 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 evening, which can drop the price by up to 35% versus a flight in the morning.
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 December 16, 2024.
Travelers seeking maximum savings on their Chicago to Costa Rica flight should consider departing on Wednesday at noon when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Costa Rica
Explore weekly flight availability from Chicago to Costa Rica. 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 diciembre 4, 2025.
The most flights from CHI to CR0 are scheduled on a Wednesday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
How often are flights from Chicago to Costa Rica delayed?
About 11% of weekly flights between Chicago and Costa Rica have experienced delays in the past year, with the average delay time being 196 minutes.
What is the most punctual flight time for Chicago to Costa Rica flights?
Historically, flights departing in the evening are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Monday tends to have the lowest number of delays on this route, whereas Wednesday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Costa Rica flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.
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 diciembre 4, 2025.
Read reviews from past customers who have flown Southwest, Copa Airlines, and United Airlines from Chicago to Costa Rica. 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.
Crew
Food
Comfort
Overall
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Crew
Food
Comfort
Overall
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Crew
Food
Comfort
Overall
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Crew
Food
Comfort
Overall
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Crew
Food
Comfort
Overall
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Crew
Food
Comfort
Overall
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
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.
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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 diciembre 4, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$221 | Average$687 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$259 | Average$391 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$307 | Average$462 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$309 | Average$511 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$345 | Average$796 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$347 | Average$677 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$394 | Average$643 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$425 | Average$706 | FlexibilityNo cancel fee | On-time69% |