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Flights from San Jose to Chicago
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Flights from San Jose to Chicago Starting at NZD 277

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

  • One way
  • Round-trip
      • Cheapest nonstop
        SJO14:05
        5h 25m
        Nonstop
        ORD19:30
        Sat, Mar 8|San Jose - Chicago|United Airlines
        NZD 538NZD 751
        28% OFF
        28% OFF
        NZD 751NZD 538

        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 538 including taxes and charges.

      • SJO13:05
        5h 25m
        Nonstop
        ORD19:30
        Sun, Mar 9|San Jose - Chicago|United Airlines
        NZD 541NZD 751
        28% OFF
        28% OFF
        NZD 751NZD 541

        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 541 including taxes and charges.

      • SJO12:55
        9h 9m
        1 stop
        MDW22:04
        Sat, Mar 1|San Jose - Chicago|Frontier Airlines
        NZD 277NZD 751
        63% OFF
        63% OFF
        NZD 751NZD 277

        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 277 including taxes and charges.

      • SJO13:07
        23h 55m
        1 stop
        ORD14:02
        Sat, Apr 26|San Jose - Chicago|Frontier Airlines
        NZD 317
        NZD 317

        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 317 including taxes and charges.

      • SJO14:49
        17h 16m
        1 stop
        ORD09:05
        Tue, Mar 11|San Jose - Chicago|Jetblue Airways
        NZD 330
        NZD 330

        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 330 including taxes and charges.

      • SJO14:43
        13h 54m
        1 stop
        ORD04:37
        Thu, Feb 20|San Jose - Chicago|Volaris Costa Rica
        NZD 334
        NZD 334

        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 334 including taxes and charges.

      • SJO14:43
        13h 54m
        1 stop
        ORD04:37
        Thu, Feb 27|San Jose - Chicago|Volaris Costa Rica
        NZD 334
        NZD 334

        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 334 including taxes and charges.

      • SJO14:43
        13h 54m
        1 stop
        ORD04:37
        Wed, Mar 5|San Jose - Chicago|Volaris Costa Rica
        NZD 334
        NZD 334

        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 334 including taxes and charges.

      • SJO14:43
        13h 54m
        1 stop
        ORD04:37
        Wed, Feb 19|San Jose - Chicago|Volaris Costa Rica
        NZD 336
        NZD 336

        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 336 including taxes and charges.

      • SJO14:43
        13h 54m
        1 stop
        ORD05:37
        Wed, Mar 19|San Jose - Chicago|Volaris Costa Rica
        NZD 351
        NZD 351

        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 351 including taxes and charges.

      • SJO01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Tue, Feb 25|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

    02:15

    SJO

    2.2h

    05:25

    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

    12:32

    MCO

    SMTWTFS

  5. F91457

    Frontier Airlines

    13:13

    MCO

    3.0h

    15:12

    MDW

    SMTWTFS

  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

    10:03

    BWI

    2.1h

    11:09

    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

    20:48

    TPA

    2.9h

    22:40

    MDW

    S-TWTF-

  15. B61696

    Jetblue Airways

    12:40

    SJO

    3.4h

    18:06

    MCO

    SMTWTFS
    Search

  16. F92041

    Frontier Airlines

    07:05

    MCO

    3.4h

    09:27

    ORD

    S-TWTFS

  17. F9214

    Frontier Airlines

    13:15

    SJO

    4.4h

    19:41

    ATL

    -----F-
    Search

  18. DL1063

    Delta Air Lines

    08:22

    ATL

    1.9h

    09:18

    MDW

    SMTWTFS

  19. F9214

    Frontier Airlines

    13:15

    SJO

    4.4h

    19:41

    ATL

    -----F-
    Search

  20. F92779

    Frontier Airlines

    22:37

    ATL

    2.0h

    23:39

    MDW

    S--WTFS

  21. CM145

    Copa Airlines

    14:29

    SJO

    1.4h

    16:52

    PTY

    SMTWTFS
    Search

  22. CM285

    Copa Airlines

    18:05

    PTY

    3.5h

    21:38

    MCO

    SMTWTFS

  23. F92041

    Frontier Airlines

    07:05

    MCO

    3.4h

    09:27

    ORD

    S-TWTFS

  24. Q64050

    Volaris Costa Rica

    14:48

    SJO

    3.0h

    17:45

    MEX

    SMTWTFS
    Search

  25. Y4700

    Volaris

    00:40

    MEX

    4.0h

    05:42

    ORD

    SMTWTFS
Find more flights and airlines

Find the best time to fly from San Jose to Chicago

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.

Airlines Flying from San Jose to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Delta Air Lines logoDelta Air LinesVolaris Costa Rica logoVolaris Costa Rica

FAQ

  • 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 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 San Jose (SJO) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around NZD 1,023.

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

    It takes around 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. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

  • 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.

How to find a cheap flight from San Jose to Chicago

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 San Jose to Chicago. 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 Information from San Jose to Chicago

Cheapest nonstop flight priceNZD 277
Cheapest round-trip ticket priceNZD 808
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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