On this page, you can choose and purchase flight tickets for the route from Chicago to San Jose. The total distance between the cities is 3,557 km, and flights on this route typically operate about once a week.
The primary carrier on this route is United Airlines. Since ticket prices depend on the season and flight load, we recommend using the price dynamics chart and checking information in advance on how to get to Chicago airport and leave San Jose airport upon arrival.
Below is a calendar of the lowest flight ticket prices for Chicago — San José by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $198 in J, and the most expensive are around $344 in r. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.
Chicago → San José, average one-way price
| Month | Average price | Level | Month | Average price | Level | Month | Average price | Level |
|---|---|---|---|---|---|---|---|---|
| Jan | $328 | high | May | $259 | low | Sep | $249 | low |
| Feb | $319 | medium | Jun | $278 | medium | Oct | $239 | low |
| Mar | $339 | high | Jul | $299 | medium | Nov | $270 | medium |
| Apr | $309 | medium | Aug | $278 | medium | Dec | $359 | high |
Some values are estimated based on seasonality.
The climate in San Jose is characterized by consistent warmth, with peak temperatures reaching 25.2°C in April. October is the rainiest month, with over 550 mm of precipitation, while the dry season falls in January and February.
The lowest flight cost is recorded in January, starting $198. Ticket prices increase significantly during the summer: in June, fares start $405, making it one of the most expensive months to plan your trip.
The best time to book is considered to be February, when the weather remains dry and ticket prices are affordable — starting $201. It is best to avoid the period from September to November due to the peak of the tropical rainy season.
Regular service on this route is provided by United Airlines, which operates about one flight per week. Most flights include connections at major US hubs, though the availability of direct flights depends on the seasonal schedule. You can find detailed information about departure days and travel times in the interactive list below.
Flights Chicago — San José depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Juan Santamaria International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.
With a distance of about 3,557 km, the travel time for a direct flight is approximately 4 hours and 15 minutes. However, most routes involve connections, which increases the total travel time.
The primary carrier on this route is United Airlines (UA), offering regular flights from the USA to Costa Rica.
Direct flights between these cities are rare; most options involve one or two connections. The current schedule is available in the search results for specific dates.
Airfares change constantly based on the season and demand; you can see the current lowest price in the low price calendar on this page.
All international flights arrive at the country's main airport — Juan Santamaría (SJO), which serves San Jose.
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