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San Jose to Midway International Airport flight
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Cheap Flights from San Jose to Midway International Airport

  • One way
  • Round-trip
      • SJO12:55 pm
        9h 9m
        1 stop
        MDW10:04 pm
        San Jose - Chicago|Sat, Feb 15|Frontier Airlines
        NZD 322NZD 663
        51% OFF
        51% OFF
        NZD 663NZD 322

        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 NZD 322 including taxes and charges.

      • SJO12:55 pm
        9h 9m
        1 stop
        MDW10:04 pm
        San Jose - Chicago|Sat, Mar 1|Frontier Airlines
        NZD 338NZD 663
        49% OFF
        49% OFF
        NZD 663NZD 338

        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 338 including taxes and charges.

      • SJO10:40 am
        10h 9m
        1 stop
        MDW08:49 pm
        San Jose - Chicago|Thu, Jan 9|Frontier Airlines
        NZD 366NZD 663
        45% OFF
        45% OFF
        NZD 663NZD 366

        Choose Frontier Airlines flights from San Jose to Chicago. The one-way connecting flight with Frontier Airlines departs from Juan Santamaria International Airport on Thu, Jan 9, arriving at Midway International Airport. One-way Prices start from NZD 366 including taxes and charges.

      • SJO12:55 pm
        9h 9m
        1 stop
        MDW10:04 pm
        San Jose - Chicago|Sat, Feb 22|Frontier Airlines
        NZD 371
        NZD 371

        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 22, arriving at Midway International Airport. One-way Prices start from NZD 371 including taxes and charges.

      • SJO03:34 pm
        27h 55m
        1 stop
        MDW07:29 pm
        San Jose - Chicago|Wed, Feb 19|Jetblue Airways
        NZD 414
        NZD 414

        Choose Jetblue Airways flights from San Jose to Chicago. The one-way connecting flight with Jetblue Airways departs from Juan Santamaria International Airport on Wed, Feb 19, arriving at Midway International Airport. One-way Prices start from NZD 414 including taxes and charges.

      • SJO02:34 pm
        19h 54m
        1 stop
        MDW10:28 am
        San Jose - Chicago|Sun, Feb 9|Jetblue Airways
        NZD 421
        NZD 421

        Choose Jetblue Airways flights from San Jose to Chicago. The one-way connecting flight with Jetblue Airways departs from Juan Santamaria International Airport on Sun, Feb 9, arriving at Midway International Airport. One-way Prices start from NZD 421 including taxes and charges.

      • SJO11:59 pm
        23h 1m
        1 stop
        MDW11:00 pm
        San Jose - Chicago|Wed, Feb 12|Jetblue Airways
        NZD 479
        NZD 479

        Choose Jetblue Airways flights from San Jose to Chicago. The one-way connecting flight with Jetblue Airways departs from Juan Santamaria International Airport on Wed, Feb 12, arriving at Midway International Airport. One-way Prices start from NZD 479 including taxes and charges.

      • SJO11:59 pm
        18h 46m
        1 stop
        MDW06:45 pm
        San Jose - Chicago|Mon, Feb 10|Jetblue Airways
        NZD 521
        NZD 521

        Choose Jetblue Airways flights from San Jose to Chicago. The one-way connecting flight with Jetblue Airways departs from Juan Santamaria International Airport on Mon, Feb 10, arriving at Midway International Airport. One-way Prices start from NZD 521 including taxes and charges.

      • SJO11:59 pm
        18h 46m
        1 stop
        MDW06:45 pm
        San Jose - Chicago|Tue, Feb 11|Jetblue Airways
        NZD 521
        NZD 521

        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, Feb 11, arriving at Midway International Airport. One-way Prices start from NZD 521 including taxes and charges.

      • SJO10:28 pm
        13h 22m
        1 stop
        MDW12:50 pm
        San Jose - Chicago|Wed, Mar 26|United Airlines
        NZD 522
        NZD 522

        Choose United Airlines flights from San Jose to Chicago. The one-way connecting flight with United Airlines departs from Juan Santamaria International Airport on Wed, Mar 26, arriving at Midway International Airport. One-way Prices start from NZD 522 including taxes and charges.

      • SJO01:00 pm
        3h 5m
        Nonstop
        MDW02:00 pm
        San Jose - Chicago|Mon, Jan 13|Frontier Airlines
        Find More Flights
        Find More Flights

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

Selected Airlines from San Jose to Midway International Airport

Frontier Airlines
From NZD 322
United Airlines
From NZD 366
Volaris El Salvador
From NZD 374
Copa Airlines
From NZD 393
Jetblue Airways
From NZD 401
avianca
From NZD 440
Southwest Airlines
From NZD 578
Aeromexico
From NZD 586
Delta Air Lines
From NZD 603
Alaska Airlines
From NZD 888

Find more flights and airlines

There are 1 airport(s) in San Jose. Discover the top routes now!

  • 13.49 km from downtown San Jose
    Juan Santamaria International Airport
    Tickets From
    NZD 322
Flight Schedule from San Jose to Midway International Airport
Flight info.
Departure
Arrival
Weekly Schedule

  1. DL1756

    Delta Air Lines

    01:20 pm

    SJO

    4.3h

    07:35 pm

    ATL

    SMTWTFS
    Search

  2. DL1076

    Delta Air Lines

    09:30 pm

    ATL

    1.9h

    10:24 pm

    MDW

    SMTWTFS

  3. F9214

    Frontier Airlines

    01:29 pm

    SJO

    4.4h

    07:51 pm

    ATL

    ---W---
    Search

  4. F92779

    Frontier Airlines

    08:50 pm

    ATL

    2.0h

    09:52 pm

    MDW

    SMTWTFS

  5. AV693

    avianca

    02:04 am

    SJO

    2.2h

    05:14 am

    BOG

    SMTWTFS
    Search

  6. AV216

    avianca

    09:54 am

    BOG

    4.3h

    03:10 pm

    MCO

    SMTWTFS

  7. F91457

    Frontier Airlines

    05:28 pm

    MCO

    3.0h

    07:29 pm

    MDW

    SMTWTFS

  8. CM461

    Copa Airlines

    04:10 am

    SJO

    1.4h

    06:33 am

    PTY

    SMTWTFS
    Search

  9. CM708

    Copa Airlines

    09:22 am

    PTY

    4.9h

    03:15 pm

    BWI

    S-T--FS

  10. F93087

    Frontier Airlines

    07:09 pm

    BWI

    2.0h

    08:08 pm

    MDW

    S-T-TF-

  11. CM465

    Copa Airlines

    05:52 am

    SJO

    1.4h

    08:15 am

    PTY

    SMTWTFS
    Search

  12. CM867

    Copa Airlines

    09:30 am

    PTY

    3.5h

    02:00 pm

    MCO

    S--WT-S

  13. F91457

    Frontier Airlines

    05:28 pm

    MCO

    3.0h

    07:29 pm

    MDW

    SMTWTFS

  14. CM465

    Copa Airlines

    05:52 am

    SJO

    1.4h

    08:15 am

    PTY

    SMTWTFS
    Search

  15. CM708

    Copa Airlines

    09:22 am

    PTY

    4.9h

    03:15 pm

    BWI

    S-T--FS

  16. F93087

    Frontier Airlines

    07:09 pm

    BWI

    2.0h

    08:08 pm

    MDW

    S-T-TF-

  17. UA1172

    United Airlines

    06:30 am

    SJO

    3.9h

    10:24 am

    IAH

    SMTWTFS
    Search

  18. UA1501

    United Airlines

    12:25 pm

    IAH

    2.3h

    03:42 pm

    TPA

    -MTWTFS

  19. F93899

    Frontier Airlines

    08:45 pm

    TPA

    2.9h

    10:36 pm

    MDW

    ---W--S

  20. UA1172

    United Airlines

    06:30 am

    SJO

    3.9h

    10:24 am

    IAH

    SMTWTFS
    Search

  21. F93282

    Frontier Airlines

    09:41 am

    IAH

    2.5h

    12:10 pm

    MDW

    SM-WT-S

  22. DL1794

    Delta Air Lines

    07:00 am

    SJO

    4.1h

    01:06 pm

    ATL

    SMTWTFS
    Search

  23. DL1005

    Delta Air Lines

    02:48 pm

    ATL

    1.9h

    04:45 pm

    DTW

    SMTWTFS

  24. DL3869

    Delta Air Lines

    04:48 pm

    DTW

    1.4h

    05:10 pm

    MDW

    SMTWTFS

  25. CM763

    Copa Airlines

    08:46 am

    SJO

    1.4h

    11:09 am

    PTY

    SMTWTFS
    Search

  26. CM476

    Copa Airlines

    12:56 pm

    PTY

    6.3h

    06:17 pm

    DEN

    SMTWTFS

  27. F92210

    Frontier Airlines

    08:55 pm

    DEN

    2.4h

    12:21 am

    MDW

    SMTWTFS
Find more flights and airlines

Flight Info of Flights from San Jose to Midway International Airport

Cheapest round-trip ticket priceNZD 927
Cheapest nonstop flight priceNZD 273
Off-season for travelOctober
Peak season for travelMarch

FAQs for San Jose to Midway International Airport Flights

  • 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 1,033.

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

    It takes around 7 hours 3 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 and avianca.

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