Cheap flights from Chicago to San Jose from $159

The month of December is, on average, the cheapest month to fly to San Jose, California from Chicago, with most prices found around $410. If you are unable to visit San Jose, California during the month of December, then departing from Chicago during the month July is also very affordable. Most momondo users find prices during this month for around $412.

On average, the least expensive day to fly to San Jose, California from Chicago is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $430. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to San Jose, California for around $750.

The cheapest time of day to fly to San Jose, California is at noon when flights can be purchased for as low as $385. In the evening is when there is more demand to fly to San Jose, California, so prices are often more expensive at around $519 per ticket.

Fly from Chicago Midway to San Jose for the best Chicago - San Jose flight prices

You are more likely to see cheaper flights to San Jose, California from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San Jose, California for around $468 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Jose, California from Chicago for as low as $226 on momondo.

There are 4 cabin classes available to choose from on Chicago to San Jose, California 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 36% on your flight if you consider stops on a Chicago to San Jose, California flight.

As of November 2026, prices for Chicago to San Jose, California flights are approximately 60% more expensive when compared to flights at the same time last year.

Southwest, United Airlines, and Delta are the most popular carriers operating from Chicago to San Jose

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to San Jose, California from Chicago according to our data. United Airlines is the first choice among our users, with 59% of people opting to fly with this airline when traveling to San Jose, California. Keep in mind that there are 7 different airlines that fly to San Jose, California on a routine basis, so you have a few additional options to choose from.

Seattle (SEA) was the most common stop: 44% of momondo users choosing 1-stop flights on this route connected there.

Flights via Seattle (SEA) offer the lowest average round-trip price of $216.

Flights connecting via San Diego (SAN) have the shortest average one-way travel time: 6h 54m.

San Diego (SAN) has the shortest average layover time for this route: 0h 47m.

The number of flights available between Chicago and San Jose, California is 4 per day as of November 2026. The most frequent departure time is 9:00AM, with 62% of daily flights leaving at noon.

29 flights are operational weekly from Chicago to San Jose, California as of November 2026. The most popular departure day for this route is Mon, with 24% of flights per week taking off on this day.