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Cheap flight deals from San Jose to Chicago Starting at NZD 298

Discover our range of affordable one-way and round-trip flights from San Jose to Chicago and kick-start your next adventure today!

  • One way
  • Round-trip
      • Cheapest nonstop
        SJO14:05
        5h 25m
        Nonstop
        ORD19:30
        Sat, Mar 8|San Jose - Chicago|United Airlines
        NZD 536NZD 709
        24% OFF
        24% OFF
        NZD 709NZD 536

        Choose United Airlines flights from San Jose to Chicago. The one-way direct flight with United Airlines departs from Juan Santamaria International Airport on Sat, Mar 8, arriving at O'Hare International Airport. One-way Prices start from NZD 536 including taxes and charges.

      • SJO13:05
        5h 25m
        Nonstop
        ORD19:30
        Sun, Mar 9|San Jose - Chicago|United Airlines
        NZD 539NZD 709
        24% OFF
        24% OFF
        NZD 709NZD 539

        Choose United Airlines flights from San Jose to Chicago. The one-way direct flight with United Airlines departs from Juan Santamaria International Airport on Sun, Mar 9, arriving at O'Hare International Airport. One-way Prices start from NZD 539 including taxes and charges.

      • SJO12:55
        9h 9m
        1 stop
        MDW22:04
        Sat, Mar 1|San Jose - Chicago|Frontier Airlines
        NZD 298NZD 709
        57% OFF
        57% OFF
        NZD 709NZD 298

        Choose Frontier Airlines flights from San Jose to Chicago. The one-way connecting flight with Frontier Airlines departs from Juan Santamaria International Airport on Sat, Mar 1, arriving at Midway International Airport. One-way Prices start from NZD 298 including taxes and charges.

      • SJO13:07
        21h 49m
        1 stop
        ORD11:56
        Sat, Apr 26|San Jose - Chicago|Frontier Airlines
        NZD 298
        NZD 298

        Choose Frontier Airlines flights from San Jose to Chicago. The one-way connecting flight with Frontier Airlines departs from Juan Santamaria International Airport on Sat, Apr 26, arriving at O'Hare International Airport. One-way Prices start from NZD 298 including taxes and charges.

      • SJO14:49
        17h 16m
        1 stop
        ORD09:05
        Tue, Mar 11|San Jose - Chicago|Jetblue Airways
        NZD 329
        NZD 329

        Choose Jetblue Airways flights from San Jose to Chicago. The one-way connecting flight with Jetblue Airways departs from Juan Santamaria International Airport on Tue, Mar 11, arriving at O'Hare International Airport. One-way Prices start from NZD 329 including taxes and charges.

      • SJO14:43
        13h 54m
        1 stop
        ORD04:37
        Thu, Feb 20|San Jose - Chicago|Volaris Costa Rica
        NZD 333
        NZD 333

        Choose Volaris Costa Rica flights from San Jose to Chicago. The one-way connecting flight with Volaris Costa Rica departs from Juan Santamaria International Airport on Thu, Feb 20, arriving at O'Hare International Airport. One-way Prices start from NZD 333 including taxes and charges.

      • SJO14:43
        13h 54m
        1 stop
        ORD04:37
        Thu, Feb 27|San Jose - Chicago|Volaris Costa Rica
        NZD 333
        NZD 333

        Choose Volaris Costa Rica flights from San Jose to Chicago. The one-way connecting flight with Volaris Costa Rica departs from Juan Santamaria International Airport on Thu, Feb 27, arriving at O'Hare International Airport. One-way Prices start from NZD 333 including taxes and charges.

      • SJO14:43
        13h 54m
        1 stop
        ORD04:37
        Wed, Mar 5|San Jose - Chicago|Volaris Costa Rica
        NZD 333
        NZD 333

        Choose Volaris Costa Rica flights from San Jose to Chicago. The one-way connecting flight with Volaris Costa Rica departs from Juan Santamaria International Airport on Wed, Mar 5, arriving at O'Hare International Airport. One-way Prices start from NZD 333 including taxes and charges.

      • SJO14:43
        13h 54m
        1 stop
        ORD04:37
        Wed, Feb 19|San Jose - Chicago|Volaris Costa Rica
        NZD 335
        NZD 335

        Choose Volaris Costa Rica flights from San Jose to Chicago. The one-way connecting flight with Volaris Costa Rica departs from Juan Santamaria International Airport on Wed, Feb 19, arriving at O'Hare International Airport. One-way Prices start from NZD 335 including taxes and charges.

      • SJO14:43
        13h 54m
        1 stop
        ORD05:37
        Wed, Mar 19|San Jose - Chicago|Volaris Costa Rica
        NZD 350
        NZD 350

        Choose Volaris Costa Rica flights from San Jose to Chicago. The one-way connecting flight with Volaris Costa Rica departs from Juan Santamaria International Airport on Wed, Mar 19, arriving at O'Hare International Airport. One-way Prices start from NZD 350 including taxes and charges.

      • SJO01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Wed, Feb 26|San Jose - Chicago|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.

San Jose to Chicago flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. AV693

    avianca

    01:55

    SJO

    2.3h

    05:10

    BOG

    SMTWTFS
    Search

  2. AV262

    avianca

    07:00

    BOG

    6.3h

    12:15

    ORD

    -MTWT-S

  3. CM461

    Copa Airlines

    04:10

    SJO

    1.4h

    06:33

    PTY

    SMTWTFS
    Search

  4. CM446

    Copa Airlines

    08:02

    PTY

    3.5h

    11:33

    MCO

    SMTWTFS

  5. F91457

    Frontier Airlines

    17:26

    MCO

    3.0h

    19:29

    MDW

    SM-WTFS

  6. CM461

    Copa Airlines

    04:10

    SJO

    1.4h

    06:33

    PTY

    SMTWTFS
    Search

  7. CM708

    Copa Airlines

    09:22

    PTY

    4.9h

    15:15

    BWI

    S-T--FS

  8. F93087

    Frontier Airlines

    16:11

    BWI

    2.2h

    17:23

    MDW

    S-T-TF-

  9. CM465

    Copa Airlines

    05:52

    SJO

    1.4h

    08:15

    PTY

    SMTWTFS
    Search

  10. CM393

    Copa Airlines

    09:04

    PTY

    3.4h

    13:26

    TPA

    SMTWTFS

  11. F92317

    Frontier Airlines

    20:18

    TPA

    3.1h

    22:25

    ORD

    -----F-

  12. CM465

    Copa Airlines

    05:52

    SJO

    1.4h

    08:15

    PTY

    SMTWTFS
    Search

  13. CM393

    Copa Airlines

    09:04

    PTY

    3.4h

    13:26

    TPA

    SMTWTFS

  14. F93899

    Frontier Airlines

    20:59

    TPA

    2.8h

    22:47

    MDW

    S-TWTF-

  15. CM465

    Copa Airlines

    05:52

    SJO

    1.4h

    08:15

    PTY

    SMTWTFS
    Search

  16. CM393

    Copa Airlines

    09:04

    PTY

    3.4h

    13:26

    TPA

    SMTWTFS

  17. AA3045

    American Airlines

    17:34

    TPA

    3.1h

    19:38

    ORD

    SMTWTFS

  18. B61696

    Jetblue Airways

    12:40

    SJO

    3.4h

    18:06

    MCO

    SMTWTFS
    Search

  19. F92041

    Frontier Airlines

    05:05

    MCO

    3.1h

    07:09

    ORD

    S-TWTFS

  20. F9214

    Frontier Airlines

    13:15

    SJO

    4.4h

    19:41

    ATL

    -----F-
    Search

  21. F92779

    Frontier Airlines

    22:45

    ATL

    2.0h

    23:47

    MDW

    S--WTFS

  22. Q65192

    Volaris Costa Rica

    14:39

    SJO

    1.6h

    16:13

    GUA

    S-TWTFS
    Search

  23. UA258

    United Airlines

    22:47

    GUA

    4.7h

    05:30

    EWR

    S-T-T-S

  24. UA1994

    United Airlines

    07:20

    EWR

    2.8h

    09:07

    ORD

    SMTWTFS

  25. Q64050

    Volaris Costa Rica

    14:43

    SJO

    3.1h

    17:50

    MEX

    SMTWTFS
    Search

  26. Y4700

    Volaris

    00:40

    MEX

    4.0h

    05:42

    ORD

    SMTWTFS
Find more flights and airlines

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

These price trend charts carefully monitor and predict how flight prices from San Jose to Chicago will change. Keep a close eye on them to understand when the best time to buy your tickets is.

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 San Jose (SJO) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from San Jose to Chicago 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 San Jose (SJO) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around NZD 1,019.

  • How long does it take to fly from San Jose (SJO) to Chicago (CHI)?

    It takes about 6 hours 50 minutes to fly from San Jose (SJO) to Chicago (CHI).

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

    • The distance from O'Hare International Airport to downtown is about 25 km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14 km, by taxi about 30 minutes.

  • What time does the earliest flight from San Jose to Chicago depart?

    The earliest flight departs from San Jose (SJO) at 05:45 and arrives in Chicago (ORD) at 14:40.

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

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

  • What's the most popular airline for non-stop flights from San Jose (SJO) to Chicago (CHI)?

    American Airlines operates 2 non-stop flights from San Jose (SJO) to Chicago (CHI).

  • How many airports are there in Chicago (CHI)?

How to find a cheap flight from San Jose to Chicago

If you leave it until the last minute and forget to check some of the key information when booking tickets, prices can often end up skyrocketing. Below, you can find our top tips for getting the best value flights – from changing dates to chasing deals, there are plenty ways to keep your next trip affordable.
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 | San Jose to Chicago

Cheapest direct flight priceNZD 276
Cheapest return ticket priceNZD 805
Off-season for travelMarch
Peak season for travelMay
Flight distance3,568.5 km
Average flight time6 hours 50 minutes
Popular airlineAeromexico

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