Cheap flights from San José to Chicago from $204

The month of November is, on average, the cheapest month to fly to Chicago from San José, with most prices found around $111. If you’re not able to fly to Chicago in November, then August is your next best option. Flight prices from San José to Chicago during August average around $138.

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $429. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from San José to Chicago for around $511.

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from San José to Chicago during this time can be as low as $464. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $468.

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

You are more likely to see cheaper flights to Chicago from San José when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $471 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from San José for as low as $399 on momondo.

You could potentially save up to 1% on your flight if you consider stops on a San José to Chicago flight.

As of May 2026, prices for San José to Chicago flights are approximately 69% more expensive when compared to flights at the same time last year.

JetBlue, Viva, and Southwest are the most popular carriers operating from San José Juan Santamaria Intl to Chicago

American Airlines, United Airlines and Copa Airlines are the top three most popular airlines that fly to Chicago from San José according to our data. American Airlines is the first choice among our users, with 44% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 8% 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 239 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 6% of their flights experiencing any sort of delay.

Panama City (PTY) was the most common stop: 43% 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 $291.

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 7h 51m.

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