The prices shown on this page were available within the last 20 days for the specified periods and should not be considered the final price offered. Please note that availability and prices are subject to change.

Cheapest time to fly from San Jose to Chicago

If you’re planning to fly this route soon, keep in mind that the lowest fares are usually available in the middle of December. Take advantage of this period to save on your flight tickets and make the most of your trip. Please note that prices may change after your search.

Filter by

week: Dec 14 - Dec 20

Flights from just €84

€84

€231

€107

DecemberJanuary

Distance: 2,950 km

San Jose airports

Chicago airports

O'hare International Airport (ORD)How far from city centre: 22 km

Book your flight from San Jose to Chicago

Find direct and indirect flights from San Jose to Chicago (United States) with eDreams. Once you have your results, sort them by schedule or price and book the option that best suits your plans.

The lowest fare booked on this route in recent days was €84, though the price you see will depend on your travel dates and departure times.

A direct flight from San Jose to Chicago takes around 5 h and 42 m, while indirect flights will take longer.

Airports and airlines connecting San Jose and Chicago

Knowing where you set off from and where you arrive helps you organise your journey better. Consider the available airports and compare the different airlines operating on this route.

Arrival airport: O'hare International Airport (ORD)

Weather in Chicago

The best time to visit may depend on your preferred climate. In Chicago, the average temperature floats around 28ºC in the warmest months and -7ºC in the coldest ones. Keep this in mind when packing and planning any outdoor activities.

Highs: up to 29ºC
Lows: down to -9ºC
Hottest month: July
Coldest month: January
Driest month: January
Wettest month: August

How to save when flying from San Jose to Chicago

A few tips for finding cheaper flights from San Jose to Chicago:

Flexible dates: compare fares for two or three different departure days. Leaving a day earlier or later can make a noticeable difference to the price.
Baggage allowance: check what each fare includes before you book, so you aren't caught out by extra charges at the airport.
Airports on your route: confirm which airports you depart from and land at, especially if the city has more than one. This will help you plan your transfer and work out the total cost of getting around.

Looking for a bigger saving? Book a Flight + Hotel package to combine both in one booking and unlock exclusive discounts on your stay in Chicago. You can also save on a hire car by including it with your booking.

Frequently asked questions about flights from San Jose to Chicago

On average, what is the price of a San Jose to Chicago flight?

When flying from San Jose to Chicago the average price will be €204. However, this price is dependant on several other factors like seasonality or the time in advance taken when booking the route.

For flights from San Jose to Chicago, how can I find the cheapest price?

On eDreams we use machine learning to find the most economical flight between San Jose and Chicago. By taking into account the combinations of airlines, stopovers, direct flights as well as the various criteria for the journeys, our search engine allows us to offer our customers the best price under the best conditions.

When booking, when is the best time to do so in order to get the best prices for San Jose to Chicago flights?

The most popular month for flights from San Jose to Chicago are: July, December and June.

When is the best time to travel from San Jose to Chicago?

A good period of the year to visit Chicago from San Jose really depends on lots of personal preferences, price being one of the main criteria When it comes to popularity, March is the best month to fly to Chicago from San Jose, basedd on searches from our customers, followed by November and October. If you prefer to avoid the busy season and get away from the crowds April, February and July are the months with fewer searches for the route San Jose - Chicago.

What is the duration of a flight from San Jose to Chicago?

Flight time, on average, from San Jose to Chicago is usually 5 h and 50 m on average, at an average distance of 2,949.99 km, for flights for the route (which may have 1 or more stops in other cities in between).

What airlines fly from San Jose to Chicago?

Frontier Airlines

Frontier Airlines

Plan your trip

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