Cheap flight deals from Chicago to San Jose Starting at AED 2,328

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to fly from Chicago to San Jose?

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  • 16 23
  • 23 30

  • Apr

    30 6
  • 6 13
  • 13 20
  • 20 27

  • May

    27 4
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

  • When are flight tickets from Chicago (CHI) to San Jose (SJI) the cheapest?

    Airlines adjust prices for flights from Chicago to San Jose based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Chicago (CHI) to San Jose (SJI) cost?

    According to Trip.com's data, the lowest price is around AED 5,504.

  • What is the transportation method from the main airport to downtown in San Jose?

    • The distance from San Jose Airport Mindoro to downtown is about 2 km, by taxi about 20 minutes.

  • How many airports are there in San Jose (SJI)?

    There are 1 airport(s) near San Jose (SJI): San Jose Airport Mindoro.

How to find a cheap flight from Chicago to San Jose

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to San Jose. Book your flights at the right time and save more.
1
Being flexible with your dates to get the cheapest Chicago to San Jose ticket.
Tap "Date" on flight search bar to get the calender for Chicago to San Jose airfare over next 6 months in 2025.
2
Compare cheap Chicago to San Jose flight deals from over hundreds of airlines.
Compare prices from over 500 airlines with our powerful search and find the cheapest flight tickets from Chicago to San Jose.
3
Set up a Price Alert
By setting up a Price Alert for your Chicago to San Jose route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap Chicago to San Jose flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
5
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
6
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from Chicago to San Jose to get exclusive deals for you.

Flight Info | Chicago to San Jose

Off-season for travel March
Peak season for travel January
Flight distance 13,307.97 km
Popular airline American Airlines

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