Price observed over the last 3 months for a round trip.
Compare all flight tickets and find cheap flights from Chicago to San José
The cheapest flights right now
Chicago – San Jose
Outbound – Nov 14, 2026
direct
5h 18m Return – Nov 21, 2026
1 stop
9h 0m IAH
$605
yesterday
Chicago – San Jose
Outbound – Nov 14, 2026
direct
5h 18m Return – Nov 21, 2026
direct
5h 33m $602
yesterday
Chicago – San Jose
Outbound – Nov 14, 2026
1 stop
7h 59m IAH
Return – Nov 21, 2026
direct
5h 33m $642
yesterday
Chicago – San Jose
Outbound – Nov 14, 2026
1 stop
7h 52m IAH
Return – Nov 21, 2026
direct
5h 33m $640
yesterday
* Prices are in USD per passenger, including taxes, for a round trip. Prices are based on searches carried out within the last 72 hours. Please note that availability and ticket prices are subject to change and should not be considered as the final price quoted.
Cheapest flight tickets
$393
Average price of a round trip
$445
Average flight ticket price recorded over the last 3 months for a round trip.
Flight duration
5h18
A flight from Chicago to San José takes on average 5h18.
Best time
February
According to user searches, the ideal month to go to San José is February.
The best flight deals for a week
Chicago – San Jose
Outbound – Nov 14, 2026
direct
5h 18m Return – Nov 21, 2026
1 stop
9h 0m IAH
$605
yesterday
Chicago – San Jose
Outbound – Nov 14, 2026
direct
5h 18m Return – Nov 21, 2026
direct
5h 33m $602
yesterday
Chicago – San Jose
Outbound – Nov 14, 2026
1 stop
7h 59m IAH
Return – Nov 21, 2026
direct
5h 33m $642
yesterday
Chicago – San Jose
Outbound – Nov 14, 2026
1 stop
7h 52m IAH
Return – Nov 21, 2026
direct
5h 33m $640
yesterday
* Prices are in USD per passenger, including taxes, for a round trip. Prices are based on searches carried out within the last 72 hours. Please note that availability and ticket prices are subject to change and should not be considered as the final price quoted.
Tips for finding a cheap flight from Chicago to San José
Check out our tips for booking your flight to San José (Costa Rica) from Chicago (USA) at the cheapest possible price.
Usually, the cheapest month to pick up a ticket on this route is April, with an average flight ticket price of $310 (calculation over the last two years). The most touristic season corresponds to the months of December, October and May.
For the cheapest flights, it is advisable to buy your ticket at least 36 days before the departure date.
The airline offering the cheapest flight tickets is Copa Airlines. A ticket from the airline Copa Airlines to San José costs on average $419.
The airlines that offer the most flights are United Airlines and United Airlines.
Price of flight tickets from Chicago to San José
Here is some information and tips to know before booking your flight:
- Flight ticket prices range from $393 to $654
- The average price of a flight ticket is about $445
- Prices are lowest for stays in the month of April
- The month in which booking a ticket is cheaper is: October
info departure city :
Chicago, USA
airports :
Chicago-Merrill C. Meigs Field Airport (CGX)
Chicago FSS (CHI)
Chicago-Midway International Airport (MDW)
Chicago-O'Hare International Airport (ORD)
local time :
Chicago is a city in the country USA, the time zone is [[timezone]]. In Chicago, it is currently {fromLocalTime}, the temperature is on average 14°C, with a minimum of 10°C and a maximum of 20°C.
The city of Chicago (CHI) has 4 airport(s): Chicago-Merrill C. Meigs Field, Chicago FSS, Chicago-Midway and Chicago-O'Hare
destination info :
San José, Costa Rica
airports :
San José-Juan-Santamaría International Airport (SJO)
San José-Tobías Bolaños Airport (SYQ)
local time :
San José is in the country Costa Rica, the time zone is [[timezone]]. In San José, it is currently {toLocalTime}, the temperature is on average 18°C, with a minimum of 13°C and a maximum of 23°C.
The city of San José has 2 airport(s): San José-Juan-Santamaría and San José-Tobías Bolaños
Useful info about San José
What is the least touristic period to go to San José?
If you want to visit San José during the least touristic period, choose the month of February.
What is the most popular time to travel to San José?
In San José, the most popular month is December. It is during this period that the prices offered by airlines are also the highest.
When should I book my flight from Chicago to San José?
According to our data, it is recommended to book your flight 36 days before your departure. If you book your flight ticket 6 weeks before your departure, you may find a price below average. The cheapest day to book a flight from Chicago to San José is Saturday.
What are the arrival and destination airports when traveling between Chicago and San José?
When you leave, you can leave from Chicago-O'Hare, and you will arrive at San José-Juan-Santamaría.
How to reach Chicago airport from the city centre?
The airport Chicago-Merrill C. Meigs Field is located 4 km, Chicago FSS is located 29 km, Chicago-Midway is located 12 km or Chicago-O'Hare is located 29 km from the city centre. You can access it by using public transportation, taking a taxi, or renting a car.
Are there other means of transportation to go from Chicago to San José?
Airplane is the only means of transportation listed on Liligo for this journey.
Are there big differences in weather between Chicago and San José?
In summer, the average temperature is 20°C in San José and 22°C in Chicago. The average rainfall in summer is 548 mm in San José and 145 mm in Chicago. In summer, it is warmer in Chicago and it rains less in Chicago. In winter, it is colder in San José and it rains more in Chicago.
