App
Customer Support
GBP
Find Bookings
Trip.com
>
Cheap Flights
>
United States
>
Illinois
>
Chicago
>
Flights from San Jose to Chicago
Worldwide Coverage
Worldwide Coverage
Flights to over 5,000 cities
One-stop Service Guarantee
One-stop Service Guarantee
Price guaranteed upon confirmed payment, booking guaranteed once tickets issued
Secure Payment
Secure Payment
Convenient & reliable booking and payment system

Flights from San Jose to Chicago Starting at £125

For as little as £125, you can take your next adventure to Chicago without breaking the bank. Choose between one-way and return tickets from San Jose below.

  • One way
  • Round-trip
      • Cheapest nonstop
        SJO14:05
        5h 25m
        Nonstop
        ORD19:30
        Sun, Feb 9|San Jose - Chicago|United Airlines
        £268£366
        27% OFF
        27% OFF
        £366£268

        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, Feb 9, arriving at O'Hare International Airport. One-way Prices start from £268 including taxes and charges.

      • SJO14:05
        5h 25m
        Nonstop
        ORD19:30
        Sun, Jan 26|San Jose - Chicago|United Airlines
        £275£366
        25% OFF
        25% OFF
        £366£275

        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, Jan 26, arriving at O'Hare International Airport. One-way Prices start from £275 including taxes and charges.

      • SJO14:43
        13h 54m
        1 stop
        ORD04:37
        Thu, Feb 6|San Jose - Chicago|Volaris Costa Rica
        £125£366
        66% OFF
        66% OFF
        £366£125

        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 6, arriving at O'Hare International Airport. One-way Prices start from £125 including taxes and charges.

      • SJO12:55
        9h 9m
        1 stop
        MDW22:04
        Sat, Mar 1|San Jose - Chicago|Frontier Airlines
        £147
        £147

        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 £147 including taxes and charges.

      • SJO12:55
        9h 9m
        1 stop
        MDW22:04
        Sat, Feb 15|San Jose - Chicago|Frontier Airlines
        £148
        £148

        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, Feb 15, arriving at Midway International Airport. One-way Prices start from £148 including taxes and charges.

      • SJO14:52
        13h 45m
        1 stop
        ORD05:37
        Thu, Mar 13|San Jose - Chicago|Volaris Costa Rica
        £151
        £151

        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, Mar 13, arriving at O'Hare International Airport. One-way Prices start from £151 including taxes and charges.

      • SJO15:45
        20h 30m
        1 stop
        ORD12:15
        Sun, Jan 26|San Jose - Chicago|avianca
        £157
        £157

        Choose avianca flights from San Jose to Chicago. The one-way connecting flight with avianca departs from Juan Santamaria International Airport on Sun, Jan 26, arriving at O'Hare International Airport. One-way Prices start from £157 including taxes and charges.

      • SJO14:43
        13h 54m
        1 stop
        ORD04:37
        Wed, Feb 5|San Jose - Chicago|Volaris Costa Rica
        £158
        £158

        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 5, arriving at O'Hare International Airport. One-way Prices start from £158 including taxes and charges.

      • SJO14:43
        13h 54m
        1 stop
        ORD04:37
        Mon, Feb 17|San Jose - Chicago|Volaris Costa Rica
        £163
        £163

        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 Mon, Feb 17, arriving at O'Hare International Airport. One-way Prices start from £163 including taxes and charges.

      • SJO14:43
        13h 54m
        1 stop
        ORD04:37
        Wed, Feb 19|San Jose - Chicago|Volaris Costa Rica
        £163
        £163

        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 £163 including taxes and charges.

      • SJO01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Thu, Jan 30|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 Guatemala City 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

    SMTWTFS

  3. CM461

    Copa Airlines

    04:10

    SJO

    1.4h

    06:33

    PTY

    SMTWTFS
    Search

  4. CM708

    Copa Airlines

    09:22

    PTY

    4.9h

    15:15

    BWI

    S-T--FS

  5. F93087

    Frontier Airlines

    12:02

    BWI

    2.1h

    13:06

    MDW

    S---T--

  6. CM465

    Copa Airlines

    05:52

    SJO

    1.4h

    08:15

    PTY

    SMTWTFS
    Search

  7. CM708

    Copa Airlines

    09:22

    PTY

    4.9h

    15:15

    BWI

    S-T--FS

  8. F93087

    Frontier Airlines

    12:02

    BWI

    2.1h

    13:06

    MDW

    S---T--

  9. AV650

    avianca

    06:10

    SJO

    1.6h

    07:45

    GUA

    S-T-T-S
    Search

  10. AV630

    avianca

    08:40

    GUA

    4.6h

    13:15

    ORD

    --T-T-S

  11. UA1553

    United Airlines

    06:40

    SJO

    6.5h

    11:07

    LAX

    -----FS
    Search

  12. UA1897

    United Airlines

    14:40

    LAX

    2.5h

    18:09

    DEN

    SMTWTFS

  13. F92210

    Frontier Airlines

    20:55

    DEN

    2.4h

    00:21

    MDW

    SMTWTFS

  14. B61696

    Jetblue Airways

    13:57

    SJO

    3.4h

    19:21

    MCO

    SMTWTFS
    Search

  15. F92041

    Frontier Airlines

    18:37

    MCO

    3.3h

    20:57

    ORD

    ----TFS

  16. Q64050

    Volaris Costa Rica

    14:47

    SJO

    3.0h

    17:44

    MEX

    SMTWTFS
    Search

  17. Y4700

    Volaris

    00:40

    MEX

    4.1h

    05:44

    ORD

    SMTWTFS

  18. Q64058

    Volaris Costa Rica

    15:31

    SJO

    3.4h

    18:52

    GDL

    -M---F-
    Search

  19. Y41702

    Volaris

    19:11

    GDL

    4.1h

    00:15

    ORD

    SMTWTFS

  20. AV654

    avianca

    16:40

    SJO

    1.5h

    18:10

    GUA

    SM-W-F-
    Search

  21. UA1907

    United Airlines

    01:30

    GUA

    2.9h

    05:23

    IAH

    SMTWTFS

  22. UA411

    United Airlines

    06:22

    IAH

    2.9h

    09:14

    ORD

    SMTWTFS

  23. AV664

    avianca

    22:45

    SJO

    6.8h

    06:30

    JFK

    --T-T-S
    Search

  24. AA3848

    American Airlines

    12:44

    EWR

    2.6h

    14:20

    ORD

    SMTWTFS
Find more flights and airlines

Find the best time to fly from San Jose to Chicago

Price trend charts are a great way of tracking how much your flights cost in the lead up to departure and can help you choose when to book your tickets. See how prices to Chicago from San Jose have changed and are set to move below.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

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 date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much are flights from San Jose (SJO) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around £473.

  • How long is the flight from San Jose (SJO) to Chicago (CHI)?

    It takes about 7 hours 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 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.

  • 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 and avianca.

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

    American Airlines operates 2 direct flights from San Jose (SJO) to Chicago (CHI).

  • How many airports 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 Information from San Jose to Chicago

Cheapest direct flight price£125
Cheapest return ticket price£446
Off-season travel monthFebruary
Peak season for travelOctober
Flight distance3,568.5km
Average flight time7 hours
Popular airlineAeromexico

Contact Us

About

Other Services

Payment Methods
Our Partners
Copyright © 2025 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd.