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

The month of September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San Jose, California averaging around $387.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $444. This is often the case because there is less demand to fly during this day of the week. On the other hand, Friday is the most expensive day to depart from San Jose, California because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $646.

Flying to Chicago O'Hare Intl Airport from San Jose, California at noon is the least expensive time of day to depart. momondo users have found prices as low as $444 when looking at flights departing at noon. Try not to purchase tickets in the evening because they tend to be around $591. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from San Jose to Chicago O'Hare Intl for the best San Jose - Chicago O'Hare Intl flight prices

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from San Jose, California when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 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 13% on your flight if you consider stops on a San Jose, California to Chicago O'Hare Intl Airport flight.

As of September 2026, prices for San Jose, California to Chicago O'Hare Intl Airport flights are approximately 41% more expensive when compared to flights at the same time last year.

Delta, Alaska Airlines, and United Airlines are the most popular carriers operating from San Jose to Chicago O'Hare Intl

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from San Jose, California according to our data. United Airlines is the first choice among our users, with 55% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 7 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

San Diego (SAN) was the most common stop: 33% 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.

The number of flights available between San Jose, California and Chicago O'Hare Intl Airport is 1 per day as of September 2026. The most frequent departure time is 6:00AM, with 50% of daily flights leaving at noon.

8 flights are operational weekly from San Jose, California to Chicago O'Hare Intl Airport as of September 2026. The most popular departure day for this route is Mon, with 25% of flights per week taking off on this day.