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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
      • SJO16:01
        18h 20m
        1 stop
        MDW10:21
        San Jose - Chicago|Sun, Dec 15|Jetblue Airways
        CAD 289CAD 467
        38% OFF
        38% OFF
        CAD 467CAD 289
      • SJO10:40
        10h 9m
        1 stop
        MDW20:49
        San Jose - Chicago|Thu, Jan 9|Frontier Airlines
        CAD 294CAD 467
        37% OFF
        37% OFF
        CAD 467CAD 294
      • SJO07:30
        18h 3m
        1 stop
        MDW01:33
        San Jose - Chicago|Sun, Nov 10|United Airlines
        CAD 318CAD 467
        32% OFF
        32% OFF
        CAD 467CAD 318
      • SJO16:14
        15h 41m
        1 stop
        MDW07:55
        San Jose - Chicago|Sun, Nov 24|Jetblue Airways
        CAD 324
        CAD 324
      • SJO15:59
        17h 32m
        1 stop
        MDW09:31
        San Jose - Chicago|Sun, Dec 22|Jetblue Airways
        CAD 377
        CAD 377
      • SJO14:20
        9h 19m
        1 stop
        MDW23:39
        San Jose - Chicago|Fri, Nov 8|United Airlines
        CAD 391
        CAD 391
      • SJO08:45
        14h 8m
        1 stop
        MDW22:53
        San Jose - Chicago|Tue, Nov 5|United Airlines
        CAD 393
        CAD 393
      • SJO07:05
        9h 12m
        1 stop
        MDW16:17
        San Jose - Chicago|Sun, Dec 22|Delta Air Lines
        CAD 413
        CAD 413
      • SJO08:45
        11h 42m
        1 stop
        MDW20:27
        San Jose - Chicago|Thu, Nov 21|United Airlines
        CAD 417
        CAD 417
      • SJO14:12
        7h 34m
        1 stop
        MDW21:46
        San Jose - Chicago|Sat, Nov 23|Delta Air Lines
        CAD 418
        CAD 418
      • SJO13:00
        3h 5m
        Nonstop
        MDW14:00
        San Jose - Chicago|Tue, Nov 12|Jetblue Airways
        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
Spirit Airlines
From CAD 234
Volaris El Salvador
From CAD 240
Volaris Costa Rica
From CAD 273
Jetblue Airways
From CAD 289
Frontier Airlines
From CAD 294
United Airlines
From CAD 318
Copa Airlines
From CAD 342
Southwest Airlines
From CAD 364
Delta Air Lines
From CAD 407
avianca
From CAD 426

Find more flights and airlines

Find Suitable Airport in San Jose

  • 13.49 km from central San Jose
    Juan Santamaria International Airport
    Tickets From
    CAD 234
Flight Schedule from San Jose to Midway International Airport
Flight info.
Departure
Arrival
Weekly Schedule

  1. NK1756

    Spirit Airlines

    01:57

    SJO

    2.9h

    05:50

    FLL

    SMTWTFS
    Search

  2. NK1895

    Spirit Airlines

    21:40

    FLL

    2.6h

    00:17

    BWI

    SMTWTFS

  3. F93087

    Frontier Airlines

    16:20

    BWI

    2.1h

    17:27

    MDW

    S-TWTFS

  4. CM461

    Copa Airlines

    04:09

    SJO

    1.4h

    06:33

    PTY

    SMTWTFS
    Search

  5. CM393

    Copa Airlines

    09:19

    PTY

    3.4h

    12:45

    TPA

    SMTWTFS

  6. F93899

    Frontier Airlines

    19:16

    TPA

    2.7h

    20:59

    MDW

    ---W--S

  7. CM461

    Copa Airlines

    04:09

    SJO

    1.4h

    06:33

    PTY

    SMTWTFS
    Search

  8. CM708

    Copa Airlines

    09:22

    PTY

    4.8h

    14:11

    BWI

    S-T--FS

  9. F93087

    Frontier Airlines

    16:20

    BWI

    2.1h

    17:27

    MDW

    S-TWTFS

  10. AV650

    avianca

    05:05

    SJO

    1.3h

    06:25

    SAL

    -M-W-F-
    Search

  11. AV368

    avianca

    08:00

    SAL

    3.2h

    11:10

    IAH

    SMTWTFS

  12. F91680

    Frontier Airlines

    15:36

    IAH

    2.5h

    18:07

    MDW

    ---W---

  13. CM465

    Copa Airlines

    05:51

    SJO

    1.4h

    08:15

    PTY

    SMTWTFS
    Search

  14. CM708

    Copa Airlines

    09:22

    PTY

    4.8h

    14:11

    BWI

    S-T--FS

  15. F93087

    Frontier Airlines

    16:20

    BWI

    2.1h

    17:27

    MDW

    S-TWTFS

  16. UA1447

    United Airlines

    08:45

    SJO

    3.9h

    12:39

    IAH

    SMTWTFS
    Search

  17. F93282

    Frontier Airlines

    20:15

    IAH

    2.5h

    22:42

    MDW

    SMTWTFS

  18. WN502

    Southwest Airlines

    09:55

    SJO

    3.2h

    14:05

    MCO

    SMTWTFS
    Search

  19. WN2711

    Southwest Airlines

    18:45

    MCO

    2.9h

    20:40

    MDW

    S--WTFS

  20. NK1310

    Spirit Airlines

    12:25

    SJO

    3.3h

    16:42

    MCO

    SMTWTFS
    Search

  21. F93975

    Frontier Airlines

    22:55

    MCO

    1.6h

    00:32

    ATL

    SMTWTFS

  22. F92779

    Frontier Airlines

    22:23

    ATL

    2.0h

    23:24

    MDW

    SMTWTFS

  23. DL1756

    Delta Air Lines

    14:19

    SJO

    4.2h

    19:31

    ATL

    SMTWTFS
    Search

  24. DL1076

    Delta Air Lines

    21:25

    ATL

    1.9h

    22:20

    MDW

    SMTWTFS

  25. UA1099

    United Airlines

    14:20

    SJO

    3.9h

    18:14

    IAH

    SMTWTFS
    Search

  26. F93282

    Frontier Airlines

    20:15

    IAH

    2.5h

    22:42

    MDW

    SMTWTFS
Find more flights and airlines

Flight Info of Flights from San Jose to Midway International Airport

Cheapest return ticket priceCAD 641
Cheapest direct flight priceCAD 223
Off-season travel monthOctober
Peak season for travelJanuary

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 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 CAD 830.

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

    It takes about 5 hours 25 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 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.

  • 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)?

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