Cheap flights from San Jose, California to Illinois from $170

The cheapest month to fly to Illinois from San Jose, California is in April. Flight prices, which tend to average around $405, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of April, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $416.

The cheapest day to depart from San Jose, California to Illinois is on a Wednesday when prices can be found for as low as $465. Flights from San Jose, California to Illinois on a Sunday will generally be more expensive and average around $670. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Our most recent data shows that the best time of day to fly to Illinois is at noon. Flights from San Jose, California to Illinois during this time can be as low as $453. Flights in the morning are often more expensive with an average ticket price of $554.

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

You are more likely to see cheaper flights to Illinois from San Jose, California when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $449 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois 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 Illinois flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Frontier, Delta, and Southwest are the most popular carriers operating from San Jose to Illinois

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Illinois from San Jose, California according to our data. United Airlines is the first choice among our users, with 49% of people opting to fly with this airline when traveling to Illinois. Keep in mind that there are 7 different airlines that fly to Illinois on a routine basis, so you have a few additional options to choose from.

As of September 2026, 2 flights take off from San Jose, California and land in Illinois each day. The most common flight departure time for this route is 11:00PM, with 43% of daily flights taking off at noon.

As of September 2026, 18 flights take off from San Jose, California and land in Illinois each week. The most common flight departure day for this route is Mon, with 22% of weekly flights taking off on this day.