Price observed over the last 3 months for a round trip.
Compare all flight tickets and find cheap flights from San José to Chicago
The cheapest flights right now
San Jose – Chicago
Outbound – Nov 21, 2026
1 stop
9h 0m IAH
Return – Nov 28, 2026
direct
5h 18m $423
2 days ago
San Jose – Chicago
Outbound – Nov 21, 2026
1 stop
9h 5m IAH
Return – Nov 28, 2026
direct
5h 18m $416
2 days ago
San Jose – Chicago
Outbound – Nov 21, 2026
direct
5h 33m Return – Nov 28, 2026
direct
5h 18m $414
2 days ago
* 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
$353
Average price of a round trip
$382
Average flight ticket price recorded over the last 3 months for a round trip.
Flight duration
5h33
A flight from San José to Chicago takes on average 5h33.
Best time
July
According to user searches, the ideal month to go to Chicago is July.
The best flight deals for a week
San Jose – Chicago
Outbound – Nov 21, 2026
1 stop
9h 0m IAH
Return – Nov 28, 2026
direct
5h 18m $423
2 days ago
San Jose – Chicago
Outbound – Nov 21, 2026
1 stop
9h 5m IAH
Return – Nov 28, 2026
direct
5h 18m $416
2 days ago
San Jose – Chicago
Outbound – Nov 21, 2026
direct
5h 33m Return – Nov 28, 2026
direct
5h 18m $414
2 days ago
* 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 San José to Chicago
Check out our tips for booking your flight to Chicago (USA) from San José (Costa Rica) at the cheapest possible price.
Usually, the cheapest month to pick up a ticket on this route is September, with an average flight ticket price of $369 (calculation over the last two years). The most touristic season corresponds to the months of November, August and October.
For the cheapest flights, it is advisable to buy your ticket at least 46 days before the departure date.
The airline offering the cheapest flight tickets is Avianca. A ticket from the airline Avianca to Chicago costs on average $354.
The airlines that offer the most flights are .
info departure city :
San José, Costa Rica
airports :
San José-Juan-Santamaría International Airport (SJO)
San José-Tobías Bolaños Airport (SYQ)
local time :
San José is a city in the country Costa Rica, the time zone is [[timezone]]. In San José, it is currently {fromLocalTime}, the temperature is on average 19°C, with a minimum of 13°C and a maximum of 26°C.
The city of San José has 2 airport(s): San José-Juan-Santamaría and San José-Tobías Bolaños
destination info :
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 in the country USA, the time zone is [[timezone]]. In Chicago, it is currently {toLocalTime}, the temperature is on average 16°C, with a minimum of 15°C and a maximum of 18°C.
The city of Chicago (CHI) has 4 airport(s): Chicago-Merrill C. Meigs Field, Chicago FSS, Chicago-Midway and Chicago-O'Hare
Useful info about Chicago
What is the least touristic period to go to Chicago?
If you want to visit Chicago during the least touristic period, choose the month of July.
What is the most popular time to travel to Chicago?
In Chicago, the most popular month is November. It is during this period that the prices offered by airlines are also the highest.
When should I book my flight from San José to Chicago?
According to our data, it is recommended to book your flight 46 days before your departure. If you book your flight ticket 7 weeks before your departure, you may find a price below average. You can also choose morning flights that are 5% cheaper than afternoon and evening flights. The cheapest day to book a flight from San José to Chicago is Saturday.
What are the arrival and destination airports when traveling between San José and Chicago?
When you leave, you can leave from San José-Juan-Santamaría, and you will arrive at Chicago-O'Hare.
How to reach San José airport from the city centre?
The airport San José-Juan-Santamaría is located 15 km or San José-Tobías Bolaños is located 7 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 San José to Chicago?
Airplane is the only means of transportation listed on Liligo for this journey.
Are there big differences in weather between San José and Chicago?
In summer, the average temperature is 22°C in Chicago and 20°C in San José. The average rainfall in summer is 145 mm in Chicago and 548 mm in San José. 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.
