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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.

  • Round-trip
  • One way

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?

We monitor flight fares to help you find the best deals effortlessly

Cheapest flights
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  • Apr

    30 6
  • 6 13
  • 13 20
  • 20 27

  • May

    27 4
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
  • 8 15
  • 15 22
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 (SJO) the cheapest?

    Airlines adjust prices for flights from Chicago to San Jose based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that 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 (SJO) cost?

    According to Trip.com's data, the lowest price is around PHP 36,275.

  • How long does it take to fly from Chicago (CHI) to San Jose (SJO) and what is the distance?

    It takes around 5 hours 14 minutes to fly from Chicago (CHI) to San Jose (SJO).

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

    • The distance from Juan Santamaria International Airport to downtown is about 15 km. It takes about 30 minutes by taxi.

  • What are the most popular airlines that fly from Chicago (CHI) to San Jose (SJO)?

    Airlines with flights from Chicago (CHI) to San Jose (SJO): United Airlines.

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
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Info | Chicago to San Jose

Cheapest one-way flight price PHP 7,683
Cheapest round-trip ticket price PHP 18,800
Off-season for travel February
Peak season for travel June
Flight distance 3,568.5 km
Average flight time 5 hours 14 minutes
Popular airline Aeromexico

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