Cheap flights from Chicago to San José from $99

In general, September is the cheapest month to fly from Chicago to San José. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $308. If you don’t want to visit San José in September, then you should wait until October to fly from Chicago, when ticket prices are also cheap, with an average price of $376.

On average, the least expensive day to fly to San José from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $513. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago to San José on a Saturday will generally be more expensive and average around $681. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Our data shows that the cheapest Chicago to San José flights are usually those with departure times in the afternoon. Our users have found flights to San José in the afternoon for as low as $510. Flights at noon are often more expensive with an average ticket price of $664.

Fly from Chicago O'Hare Intl to San José Juan Santamaria Intl for the best Chicago - San José Juan Santamaria Intl flight prices

You are more likely to see cheaper flights to San José from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San José for around $513 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San José from Chicago for as low as $435 on momondo.

There are 3 cabin classes available to choose from on Chicago to San José Juan Santamaria Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 11% on your flight if you consider stops on a Chicago to San José flight.

As of April 2026, prices for Chicago to San José flights are approximately 10% more expensive when compared to flights at the same time last year.

Frontier, Viva, and Spirit Airlines are the most popular carriers operating from Chicago to San José Juan Santamaria Intl

United Airlines, American Airlines and Spirit Airlines are the top three most popular airlines that fly to San José from Chicago according to our data. United Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to San José. Keep in mind that there are 8 different airlines that fly to San José on a routine basis, so you have a few additional options to choose from.

Historically, on average around 19% of flights between Chicago and San José have experienced a delay on any given week. The average delay length over the past 12 months has been 170 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Wednesday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 13% of their flights experiencing any sort of delay.

Fort Lauderdale (FLL) was the most common stop: 41% of momondo users choosing 1-stop flights on this route connected there.

Flights via Fort Lauderdale (FLL) offer the lowest average round-trip price of $294.

Flights connecting via Miami (MIA) have the shortest average one-way travel time: 6h 59m.

Charlotte (CLT) has the shortest average layover time for this route: 1h 19m.