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Flights from Chicago to San Jose
Cheap flight deals from Chicago to San Jose
We've found these cheap flights for you. You can book one-way or round-trip flight tickets.
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Round-trip
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One way
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ORD 16:0026h 30m2 stopsSJI 07:30Chicago - San Jose | Mon, May 12 | Cathay PacificSJI 08:2543h2 stopsORD 14:25San Jose - Chicago | Mon, May 19 | Cebu PacificAED 5,653 AED 7,94428% OFF28% OFFAED 7,944 AED 5,653
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ORD 00:3042h2 stopsSJI 07:30Chicago - San Jose | Thu, May 15 | EVA AirSJI 08:2549h 35m2 stopsORD 21:00San Jose - Chicago | Thu, May 22 | Cebu PacificAED 5,688 AED 7,94428% OFF28% OFFAED 7,944 AED 5,688
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ORD 16:0026h 30m2 stopsSJI 07:30Chicago - San Jose | Wed, May 14 | Cathay PacificSJI 08:2543h2 stopsORD 14:25San Jose - Chicago | Wed, May 21 | Cebu PacificAED 5,742 AED 7,94428% OFF28% OFFAED 7,944 AED 5,742
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ORD 16:0026h 30m2 stopsSJI 07:30Chicago - San Jose | Sun, May 11 | Cathay PacificSJI 08:0043h 25m2 stopsORD 14:25San Jose - Chicago | Sun, May 18 | Cebu PacificAED 5,78627% OFFAED 7,944 AED 5,786
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ORD 16:0026h 30m2 stopsSJI 07:30Chicago - San Jose | Mon, Jun 2 | Cathay PacificSJI 08:2543h2 stopsORD 14:25San Jose - Chicago | Mon, Jun 9 | Cebu PacificAED 5,94625% OFFAED 7,944 AED 5,946
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ORD 16:0026h 30m2 stopsSJI 07:30Chicago - San Jose | Tue, Jun 3 | Cathay PacificSJI 08:2543h2 stopsORD 14:25San Jose - Chicago | Tue, Jun 10 | Cebu PacificAED 5,94725% OFFAED 7,944 AED 5,947
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ORD 16:0026h 30m2 stopsSJI 07:30Chicago - San Jose | Wed, May 28 | Cathay PacificSJI 08:2543h2 stopsORD 14:25San Jose - Chicago | Wed, Jun 4 | Cebu PacificAED 5,96625% OFFAED 7,944 AED 5,966
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ORD 16:0026h 30m2 stopsSJI 07:30Chicago - San Jose | Sun, Jun 1 | Cathay PacificSJI 08:0043h 25m2 stopsORD 14:25San Jose - Chicago | Sun, Jun 8 | Cebu PacificAED 5,96725% OFFAED 7,944 AED 5,967
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ORD 00:3042h2 stopsSJI 07:30Chicago - San Jose | Sun, May 11 | EVA AirSJI 08:0050h2 stopsORD 21:00San Jose - Chicago | Sun, May 18 | Cebu PacificAED 5,98625% OFFAED 7,944 AED 5,986
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ORD 00:3042h2 stopsSJI 07:30Chicago - San Jose | Fri, May 30 | EVA AirSJI 08:2549h 35m2 stopsORD 21:00San Jose - Chicago | Fri, Jun 6 | Cebu PacificAED 6,19622% OFFAED 7,944 AED 6,196
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CHI 13:0017h 25m1 stopsSJI Invalid DateChicago - San Jose | Tue, May 13 | Normal AirlineSJI 15:006hNonstopCHI 16:00San Jose - Chicago | Thu, May 15 | Normal AirlineFind More FlightsFind More Flights
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CHI 13:0017h 25m1 stopsSJI Invalid DateChicago - San Jose | Tue, May 13 | Normal AirlineSearchSearch
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CHI 13:0017h 25m1 stopsSJI Invalid DateChicago - San Jose | Tue, May 13 | Normal AirlineSearchSearch
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CHI 13:0017h 25m1 stopsSJI Invalid DateChicago - San Jose | Tue, May 13 | Normal AirlineSearchSearch
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CHI 13:0017h 25m1 stopsSJI Invalid DateChicago - San Jose | Tue, May 13 | Normal AirlineSearchSearch
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CHI 13:0017h 25m1 stopsSJI Invalid DateChicago - San Jose | Tue, May 13 | Normal AirlineSearchSearch
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CHI 13:0017h 25m1 stopsSJI Invalid DateChicago - San Jose | Tue, May 13 | Normal AirlineSearchSearch
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CHI 13:0017h 25m1 stopsSJI Invalid DateChicago - San Jose | Tue, May 13 | Normal AirlineSearchSearch
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CHI 13:0017h 25m1 stopsSJI Invalid DateChicago - San Jose | Tue, May 13 | Normal AirlineSearchSearch
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CHI 13:0017h 25m1 stopsSJI Invalid DateChicago - San Jose | Tue, May 13 | Normal AirlineSearchSearch
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CHI 13:0017h 25m1 stopsSJI Invalid DateChicago - San Jose | Tue, May 13 | Normal AirlineSearchSearch
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
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Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Frequently Asked Questions
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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 5,497. -
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.
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.
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.
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.
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.
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.
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 |
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Peak season for travel | April |
Flight distance | 13,307.97 km |
Popular airline | American Airlines |
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