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Cheap flight deals from Chicago to San Jose Starting at PHP 6,119

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

  • One way
  • Round-trip
      • Cheapest nonstop
        ORD07:35 am
        5h 21m
        Nonstop
        SJO12:56 pm
        Sun, Mar 2|Chicago - San Jose|United Airlines
        PHP 13,993PHP 18,987
        26% OFF
        26% OFF
        PHP 18,987PHP 13,993

        Choose United Airlines flights from Chicago to San Jose. The one-way direct flight with United Airlines departs from O'Hare International Airport on Sun, Mar 2, arriving at Juan Santamaria International Airport. One-way Prices start from PHP 13,993 including taxes and charges.

      • ORD07:41 am
        5h 14m
        Nonstop
        SJO11:55 am
        Sat, Apr 19|Chicago - San Jose|United Airlines
        PHP 16,139PHP 18,987
        15% OFF
        15% OFF
        PHP 18,987PHP 16,139

        Choose United Airlines flights from Chicago to San Jose. The one-way direct flight with United Airlines departs from O'Hare International Airport on Sat, Apr 19, arriving at Juan Santamaria International Airport. One-way Prices start from PHP 16,139 including taxes and charges.

      • ORD05:31 pm
        19h 24m
        1 stop
        SJO11:55 am
        Fri, May 16|Chicago - San Jose|Frontier Airlines
        PHP 6,119PHP 18,987
        68% OFF
        68% OFF
        PHP 18,987PHP 6,119

        Choose Frontier Airlines flights from Chicago to San Jose. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Fri, May 16, arriving at Juan Santamaria International Airport. One-way Prices start from PHP 6,119 including taxes and charges.

      • MDW06:48 pm
        16h 43m
        1 stop
        SJO11:31 am
        Fri, Feb 28|Chicago - San Jose|Frontier Airlines
        PHP 8,073
        PHP 8,073

        Choose Frontier Airlines flights from Chicago to San Jose. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Fri, Feb 28, arriving at Juan Santamaria International Airport. One-way Prices start from PHP 8,073 including taxes and charges.

      • ORD11:45 am
        25h 51m
        1 stop
        SJO12:36 pm
        Wed, Apr 2|Chicago - San Jose|Frontier Airlines
        PHP 8,831
        PHP 8,831

        Choose Frontier Airlines flights from Chicago to San Jose. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Wed, Apr 2, arriving at Juan Santamaria International Airport. One-way Prices start from PHP 8,831 including taxes and charges.

      • ORD11:45 am
        26h 7m
        1 stop
        SJO12:52 pm
        Wed, Apr 9|Chicago - San Jose|Frontier Airlines
        PHP 9,669
        PHP 9,669

        Choose Frontier Airlines flights from Chicago to San Jose. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Wed, Apr 9, arriving at Juan Santamaria International Airport. One-way Prices start from PHP 9,669 including taxes and charges.

      • ORD05:59 pm
        18h 51m
        1 stop
        SJO11:50 am
        Fri, Mar 28|Chicago - San Jose|Frontier Airlines
        PHP 9,677
        PHP 9,677

        Choose Frontier Airlines flights from Chicago to San Jose. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Fri, Mar 28, arriving at Juan Santamaria International Airport. One-way Prices start from PHP 9,677 including taxes and charges.

      • MDW12:49 pm
        25h 55m
        1 stop
        SJO01:44 pm
        Mon, Mar 10|Chicago - San Jose|Frontier Airlines
        PHP 9,741
        PHP 9,741

        Choose Frontier Airlines flights from Chicago to San Jose. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Mon, Mar 10, arriving at Juan Santamaria International Airport. One-way Prices start from PHP 9,741 including taxes and charges.

      • ORD05:53 pm
        19h 12m
        1 stop
        SJO01:05 pm
        Fri, Mar 7|Chicago - San Jose|Frontier Airlines
        PHP 9,844
        PHP 9,844

        Choose Frontier Airlines flights from Chicago to San Jose. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Fri, Mar 7, arriving at Juan Santamaria International Airport. One-way Prices start from PHP 9,844 including taxes and charges.

      • ORD11:44 am
        10h 4m
        1 stop
        SJO08:48 pm
        Tue, Mar 18|Chicago - San Jose|Jetblue Airways
        PHP 11,272
        PHP 11,272

        Choose Jetblue Airways flights from Chicago to San Jose. The one-way connecting flight with Jetblue Airways departs from O'Hare International Airport on Tue, Mar 18, arriving at Juan Santamaria International Airport. One-way Prices start from PHP 11,272 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        SJO02:00 pm
        Mon, Mar 3|Chicago - San Jose|United Airlines
        Find More Flights
        Find More Flights

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

Chicago to San Jose Flight Time

Flight info.
Departure
Arrival
Weekly Schedule

  1. B6906

    Jetblue Airways

    01:12 pm

    ORD

    2.3h

    04:30 pm

    JFK

    SMTWTFS
    Search

  2. B61793

    Jetblue Airways

    09:48 am

    JFK

    5.3h

    01:05 pm

    SJO

    SMTWTFS

  3. Y4703

    Volaris

    01:40 am

    ORD

    4.2h

    04:50 am

    MEX

    -MTWTFS
    Search

  4. Q64051

    Volaris Costa Rica

    10:50 am

    MEX

    3.0h

    01:52 pm

    SJO

    SMTWT-S

  5. AV263

    avianca

    02:35 pm

    ORD

    5.8h

    08:25 pm

    BOG

    SMTWTFS
    Search

  6. AV692

    avianca

    10:10 pm

    BOG

    2.3h

    11:30 pm

    SJO

    SMTWTFS

  7. DL2767

    Delta Air Lines

    06:00 am

    ORD

    2.3h

    09:15 am

    LGA

    SMTWT--
    Search

  8. B61793

    Jetblue Airways

    09:48 am

    JFK

    5.3h

    01:05 pm

    SJO

    SMTWTFS

  9. AA3152

    American Airlines

    06:17 am

    ORD

    2.0h

    09:19 am

    LGA

    SMTWT-S
    Search

  10. B61793

    Jetblue Airways

    09:48 am

    JFK

    5.3h

    01:05 pm

    SJO

    SMTWTFS

  11. F92292

    Frontier Airlines

    06:44 pm

    MDW

    2.2h

    09:57 pm

    ATL

    SM-WT-S
    Search

  12. F9215

    Frontier Airlines

    10:13 am

    ATL

    4.2h

    12:22 pm

    SJO

    -----F-

  13. F9044

    Frontier Airlines

    07:00 am

    ORD

    4.0h

    10:57 am

    CUN

    SMTWTFS
    Search

  14. Q64057

    Volaris Costa Rica

    12:40 pm

    CUN

    2.1h

    01:47 pm

    SJO

    SMTWTFS

  15. F92110

    Frontier Airlines

    07:35 am

    MDW

    3.2h

    11:48 am

    MIA

    S--WTF-
    Search

  16. AA2559

    American Airlines

    07:32 pm

    MIA

    3.3h

    09:49 pm

    SJO

    SMTWTFS

  17. CM236

    Copa Airlines

    07:54 am

    ORD

    5.5h

    01:22 pm

    PTY

    SMTWTFS
    Search

  18. CM116

    Copa Airlines

    03:57 pm

    PTY

    1.4h

    04:22 pm

    SJO

    SMTWTFS

  19. AA2510

    American Airlines

    08:45 am

    ORD

    2.1h

    11:50 am

    LGA

    SMTWTFS
    Search

  20. DL988

    Delta Air Lines

    01:59 pm

    LGA

    2.3h

    04:18 pm

    ATL

    SMTWT-S

  21. DL1931

    Delta Air Lines

    11:08 am

    ATL

    4.0h

    01:05 pm

    SJO

    SMTWTFS
Find more flights and airlines

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

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

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 31,527.

  • 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 nonstop flight pricePHP 6,118
Cheapest round-trip ticket pricePHP 27,052
Off-season for travelFebruary
Peak season for travelNovember
Flight distance3,568.5 km
Average flight time5 hours 14 minutes
Popular airlineAmerican Airlines

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