$128+ 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 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
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 June 12, 2025.
Round-trip from | $289 (Mytrip) |
|---|---|
One-way from | $128 (Kiwi.com) |
Popular in | December |
Cheapest in | August |
Average price | $524 |
Good round-trip deal | $432 or less |
Good one-way deal | $242 or less |
Find 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 June 12, 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 June 12, 2025.
This Mytrip deal was found by Cheapflights users on 6/10. 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 Copa Airlines deal was found by Cheapflights users on 6/12. 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.
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 CheapOair deal was found by Cheapflights users on 6/11. 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 Frontier deal was found by Cheapflights users on 6/11. 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 Frontier 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 6/10. 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 6/10. 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 deal was found by Cheapflights users on 6/12. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This United Airlines deal was found by Cheapflights users on 6/11. 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.
This Mytrip deal was found by Cheapflights users on 6/11. 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 American Airlines deal was found by Cheapflights users on 6/12. 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 6/12. 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.
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 June 12, 2025.
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
Tue 8/26
5:05 am-4:05 pm
1 stop10h 00m
Chicago O'Hare Intl
Sat 8/30
5:25 pm-11:35 pm
1 stop7h 10m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 9/10
8:46 am-12:22 am
1 stop14h 36m
Chicago O'Hare Intl
Wed 9/24
3:07 pm-8:20 am
1 stop18h 13m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 7/1
12:28 pm-11:45 pm
1 stop10h 17m
Chicago O'Hare Intl
Mon 7/7
7:39 pm-11:19 am
1 stop16h 40m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Fri 8/29
4:13 pm-11:05 am
1 stop17h 52m
Chicago O'Hare Intl
Tue 9/2
6:34 pm-11:18 am
1 stop17h 44m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 8/16
1:47 pm-11:29 pm
1 stop8h 42m
Chicago O'Hare Intl
Sat 8/23
6:00 am-12:24 pm
1 stop7h 24m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 8/14
2:15 pm-11:48 pm
1 stop8h 33m
Chicago O'Hare Intl
Mon 8/18
6:03 am-12:55 pm
1 stop7h 52m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Tue 8/26
1:40 pm-11:20 pm
1 stop8h 40m
Chicago Midway
Sat 8/30
10:10 am-6:55 pm
1 stop9h 45m
LiberiaChicago
LIR - ORD
LIRORD
Liberia
Tue 7/8
3:25 pm-12:15 am
1 stop7h 50m
Chicago O'Hare Intl
Sun 7/20
6:00 am-2:23 pm
1 stop9h 23m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 6/21
1:00 pm-7:34 pm
Nonstop5h 34m
Chicago O'Hare Intl
Mon 6/30
9:00 pm-10:11 am
1 stop14h 11m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Sun 7/20
7:30 am-2:04 pm
2 stops29h 34m
Chicago Midway
Mon 7/28
2:54 pm-3:35 am
2 stops13h 41m
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, 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 June 12, 2025.
It’s typically best to fly out from Costa Rica to Chicago in the morning. Doing so could potentially save you 9% 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. 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 June 12, 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.
Crew
Overall
Food
Comfort
Entertainment
Boarding
Reviews
James,Apr 2025
LAX - SFO
Crew
Overall
Food
Comfort
Entertainment
Boarding
Reviews
James,Apr 2025
LAX - SFO
Crew
Overall
Food
Comfort
Entertainment
Boarding
Reviews
James,Apr 2025
LAX - SFO
Crew
Overall
Food
Comfort
Entertainment
Boarding
Reviews
James,Apr 2025
LAX - SFO
Crew
Overall
Food
Comfort
Entertainment
Boarding
Reviews
James,Apr 2025
LAX - SFO
Crew
Overall
Food
Comfort
Entertainment
Boarding
Reviews
James,Apr 2025
LAX - SFO
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.
Traveling to a place near Costa Rica?
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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 7 airlines flying from Costa Rica to Chicago
Discover the top 7 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 June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$264 | Average$412 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$314 | Average$485 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$318 | Average$488 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$425 | Average$527 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$434 | Average$563 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$437 | Average$682 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$446 | Average$570 | FlexibilityNo cancel fee | On-time71% |