Cheap flights from San José to Chicago from $214

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San José averaging around $398.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $395. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from San José because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $538.

Flying to Chicago O'Hare Intl Airport from San José in the morning is the least expensive time of day to depart. momondo users have found prices as low as $462 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $466. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from San José when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $501 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from San José for as low as $407 on momondo.

There are 2 cabin classes available to choose from on San José to Chicago O'Hare Intl Airport 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 17% on your flight if you consider stops on a San José to Chicago O'Hare Intl Airport flight.

As of August 2026, prices for San José to Chicago O'Hare Intl Airport flights are approximately 21% more expensive when compared to flights at the same time last year.

Viva and JetBlue are the most popular carriers operating from San José Juan Santamaria Intl to Chicago O'Hare Intl

American Airlines, United Airlines and Copa Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from San José according to our data. American Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 4 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 7% of flights between San José and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 254 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. Friday has historically seen more delays on average compared to the rest of the week.

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 5% of their flights experiencing any sort of delay.

Panama City (PTY) was the most common stop: 63% of momondo users choosing 1-stop flights on this route connected there.

Flights via Atlanta (ATL) offer the lowest average round-trip price of $419.

Flights connecting via Houston (IAH) have the shortest average one-way travel time: 8h 07m.

Houston (IAH) has the shortest average layover time for this route: 1h 12m.