Cheap flights from San Jose, California to Chicago from $169

The month of April is, on average, the cheapest month to fly to Chicago from San Jose, California, with most prices found around $405. If you’re not able to fly to Chicago in April, then August is your next best option. Flight prices from San Jose, California to Chicago during August average around $416.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $461. 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 Jose, California to Chicago for around $663.

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from San Jose, California to Chicago during this time can be as low as $455. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $553.

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

You are more likely to see cheaper flights to Chicago from San Jose, California when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $449 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from San Jose, California for as low as $229 on momondo.

There are 4 cabin classes available to choose from on San Jose, California to Chicago 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 10% on your flight if you consider stops on a San Jose, California to Chicago flight.

As of September 2026, prices for San Jose, California to Chicago flights are approximately 40% more expensive when compared to flights at the same time last year.

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

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from San Jose, California according to our data. United Airlines is the first choice among our users, with 51% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

San Diego (SAN) was the most common stop: 43% of momondo users choosing 1-stop flights on this route connected there.

Flights via Phoenix (PHX) offer the lowest average round-trip price of $256.

Flights connecting via Las Vegas (LAS) have the shortest average one-way travel time: 6h 05m.

Las Vegas (LAS) has the shortest average layover time for this route: 0h 53m.

As of September 2026, 3 flights take off from San Jose, California and land in Chicago each day. The most common flight departure time for this route is 11:00PM, with 37% of daily flights taking off at noon.

21 flights are operational weekly from San Jose, California to Chicago as of September 2026. The most popular departure day for this route is Mon, with 19% of flights per week taking off on this day.