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Cheap flights from San Jose to Chicago

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Find the cheapest flights from San Jose to Chicago

Cheap return flights

These are some of the best return flight deals from San Jose to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from San Jose to Chicago.

Cheap last-minute flights

Planning a quick getaway from San Jose to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without stopovers.

Cheap bus & train deals from San Jose to Chicago

Find recent round-trip train or bus tickets from San Jose to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
SJC-MDW
4h 05mdirect
MDW-SJC
4h 30mdirect
Southwest
Find Deal
SJC-ORD
4h 15mdirect
ORD-SJC
4h 36mdirect
United Airlines
Find Deal
SJC-MDW
4h 05mdirect
Southwest
Find Deal
SJC-ORD
4h 15mdirect
United Airlines
Find Deal

See travel insights to Chicago from

How to get the cheapest flight ticket from San Jose to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from San Jose, with most prices found around R6 459. If you are unable to visit Chicago during the month of September, then departing from San Jose during the month November is also very affordable. Most momondo users find prices during this month for around R6 843.

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from San Jose is 42 days out, which is when prices tend to be around R8 461. However, in the past 72 hours, people saw flights from San Jose for as low as R72 649.

How have San Jose to Chicago flight prices changed over time?

As of December 2024, prices for San Jose to Chicago flights are approximately 19% cheaper when compared to flights at the same time last year.

When to book flights from San Jose to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from San Jose to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated return price

Cheap San Jose to Chicago (SJC to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San Jose to Chicago

Direct flights

None
There are no direct flights from San Jose to Chicago. There are no popular flight routes from San Jose to Chicago.

  • How far is San Jose to Chicago by plane?

    The straight-line distance from San Jose to Chicago is 2955,8 km.

  • When did momondo last update prices for flights from San Jose Airport to Chicago?

    Prices for flights from San Jose Airport to Chicago were last updated today.

  • How old do you have to be to fly from San Jose Airport to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and stopovers. It is recommended that you verify with the airline you are booking with for travel from San Jose Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's licence and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from San Jose to Chicago?


Why use momondo?

Why should I use momondo to find a flight deal from San Jose to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from San Jose to Chicago for you.

Can I find flights from San Jose to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from San Jose which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from San Jose to Chicago?

Once you have performed a search for San Jose to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from San Jose to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from San Jose and alert you when they change.


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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago