$123+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
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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
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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 Costa Rica to Chicago
Cheapest flights from Costa Rica to ChicagoExplore 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 December 23, 2025.
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 December 23, 2025.
This Cheapflightsfares deal was found by Cheapflights users on 12/22. 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 12/22. 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 Expedia deal was found by Cheapflights users on 12/22. 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 Cheapflightsfares deal was found by Cheapflights users on 12/21. 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 Priceline deal was found by Cheapflights users on 12/22. 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.
This Mytrip deal was found by Cheapflights users on 12/22. 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 12/21. 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 Cheapflightsfares deal was found by Cheapflights users on 12/21. 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 Booking.com deal was found by Cheapflights users on 12/21. 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 Booking.com 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 12/22. 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 eDestinos deal was found by Cheapflights users on 12/22. 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.
This Expedia deal was found by Cheapflights users on 12/22. 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.
Find 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 December 23, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $266 (KAYAK) |
One-way from | $123 (Cheapflightsfares) |
Popular in | April |
Cheapest in | January |
Average price | $476 |
Good round-trip deal | $339 or less |
Good one-way deal | $148 or less |
Cheapflights Fare Finder
Use the filters below to find and compare flights from Costa Rica to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Fri 2/6
12:33 pm-11:22 am
2 stops22h 49m
Chicago O'Hare Intl
Sat 2/14
9:00 am-11:40 am
2 stops26h 40m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Mon 1/12
7:45 am-8:18 am
1 stop24h 33m
Chicago O'Hare Intl
Wed 1/28
9:23 am-3:30 pm
1 stop30h 07m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 2/11
12:33 pm-11:47 pm
2 stops11h 14m
Chicago O'Hare Intl
Wed 2/18
5:15 am-12:22 pm
1 stop7h 07m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 1/17
3:12 pm-12:08 pm
1 stop20h 56m
Chicago O'Hare Intl
Thu 1/22
8:43 pm-12:22 pm
1 stop15h 39m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Fri 2/6
12:33 pm-11:47 pm
2 stops11h 14m
Chicago O'Hare Intl
Sun 2/15
9:00 am-11:40 am
2 stops26h 40m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 1/29
12:33 pm-11:47 am
3 stops23h 14m
Chicago O'Hare Intl
Tue 2/3
10:07 am-3:20 pm
3 stops29h 13m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Sat 1/17
3:12 pm-8:03 am
1 stop16h 51m
Chicago Midway
Thu 1/22
5:01 pm-12:22 pm
2 stops19h 21m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Fri 1/30
2:05 pm-7:35 pm
Nonstop5h 30m
Chicago O'Hare Intl
Mon 2/2
7:39 am-12:56 pm
Nonstop5h 17m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 1/15
2:05 pm-7:35 pm
Nonstop5h 30m
Chicago O'Hare Intl
Mon 1/26
7:35 am-8:39 pm
1 stop13h 04m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 1/15
2:05 pm-7:35 pm
Nonstop5h 30m
Chicago O'Hare Intl
Sun 1/25
7:35 am-8:39 pm
1 stop13h 04m
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.
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, October is the cheapest month in which you can book a flight from Costa Rica to Chicago (average of $195). Flying from Costa Rica to Chicago in March is currently the most expensive (average of $338). 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 December 23, 2025.
It’s typically best to fly out from Costa Rica to Chicago in the evening. Doing so could potentially save you 25% 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 Sunday afternoons when fares are most often at their lowest. Wednesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Costa Rica to Chicago
Explore weekly flight availability from Costa Rica to Chicago. 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 December 23, 2025.
The most flights from CR0 to CHI are scheduled on a Wednesday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
How often are flights from Costa Rica to Chicago delayed?
About 12% of weekly flights between Costa Rica and Chicago have experienced delays in the past year, with the average delay time being 167 minutes.
What is the most punctual flight time for Costa Rica to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Costa Rica to Chicago flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 9% of flights being delayed.
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 December 23, 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.
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
Thomas,Dec 2025
SEA - DEN
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.
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Alternative routes for Costa Rica to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
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 December 23, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$228 | Average$354 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$249 | Average$465 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$314 | Average$452 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$332 | Average$465 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$432 | Average$580 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$463 | Average$523 | FlexibilityNo cancel fee | On-time63% |