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SJ International Airport to Midway International Airport flight
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Cheap Flight Deals from SJ International Airport to Midway International Airport

Search for flights from San Jose to Chicago and check out affordable one-way and round-trip options.

  • One way
  • Round-trip
sortSort: Price (Lowest)
  • Sort: Price (Lowest)
  • Sort: Departure (Earliest)
      • SJC16:40
        11h 10m
        1 stop
        MDW05:50
        San Jose - Chicago|Tue, May 28|Spirit Airlines
        €70€184
        62% OFF
        62% OFF
        €184€70
      • SJC08:00
        19h 50m
        1 stop
        MDW05:50
        San Jose - Chicago|Wed, May 29|Spirit Airlines
        €75€184
        59% OFF
        59% OFF
        €184€75
      • SJC07:00
        20h 50m
        1 stop
        MDW05:50
        San Jose - Chicago|Thu, May 30|Spirit Airlines
        €80€184
        56% OFF
        56% OFF
        €184€80
      • SJC16:40
        11h 10m
        1 stop
        MDW05:50
        San Jose - Chicago|Sun, Jun 2|Spirit Airlines
        €110
        €110
      • SJC16:40
        11h 10m
        1 stop
        MDW05:50
        San Jose - Chicago|Sat, Jun 1|Spirit Airlines
        €111
        €111
      • SJC09:35
        18h 15m
        1 stop
        MDW05:50
        San Jose - Chicago|Wed, May 22|Spirit Airlines
        €121
        €121
      • SJC12:35
        15h 58m
        2 stops
        MDW06:33
        San Jose - Chicago|Wed, May 29|Alaska Airlines
        €128
        €128
      • SJC10:15
        17h 14m
        2 stops
        MDW05:29
        San Jose - Chicago|Wed, Jun 12|Alaska Airlines
        €128
        €128
      • SJC14:14
        7h 36m
        1 stop
        MDW23:50
        San Jose - Chicago|Wed, May 29|American Airlines
        €135
        €135
      • SJC06:10
        8h 36m
        1 stop
        MDW16:46
        San Jose - Chicago|Sat, Jun 1|American Airlines
        €139
        €139
      • SJC13:00
        3h 5m
        Direct
        MDW14:00
        San Jose - Chicago|Tue, May 28|Spirit 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 SJ International Airport to Midway International Airport

See which airlines fly from San Jose to Chicago. Find the airline that best meets your travel needs by comparing prices and treat yourself to an enjoyable journey.

Spirit Airlines
From €70
Alaska Airlines
From €128
American Airlines
From €135
Delta Air Lines
From €148
United Airlines
From €153
Southwest Airlines
From €153
ANA airlines
Find more flights and airlines

Find Cheaper Flights from San Jose to Chicago

Explore other flights from San Jose to Chicago to find the best alternative options.

  • Cheapest
    Spirit Airlines
    SJC
    08:00
    11h 55m
    1 transfer
    ORD
    21:55
    SJ International Airport - O'Hare International Airport
    Wed, May 29Spirit Airlines
    €66
  • Spirit Airlines
    SJC
    08:00
    11h 55m
    1 transfer
    ORD
    21:55
    SJ International Airport - O'Hare International Airport
    Wed, May 29Spirit Airlines
    €66
    Find More Flights
Flight Schedule from SJ International Airport to Midway International Airport

Check the schedule for flights from San Jose to Chicago and find the flight that best matches your travel plans.

Flight info.
Departure
Arrival
Weekly Schedule

  1. AA1019

    American Airlines

    06:10

    SJC

    3.8h

    11:57

    DFW

    SMTWTFS
    Search

  2. F91888

    Frontier Airlines

    09:17

    DFW

    2.4h

    11:39

    MDW

    SMTWTFS

  3. AS3458

    Alaska Airlines

    06:15

    SJC

    1.4h

    07:39

    SAN

    SMTWTFS
    Search

  4. F92928

    Frontier Airlines

    15:28

    SAN

    3.1h

    20:32

    DFW

    SMT--FS

  5. F93000

    Frontier Airlines

    18:40

    DFW

    2.4h

    21:02

    MDW

    -M-W--S

  6. UA1417

    United Airlines

    10:50

    SJC

    2.6h

    14:29

    DEN

    S--WTFS
    Search

  7. F92946

    Frontier Airlines

    19:03

    DEN

    2.1h

    22:10

    MDW

    -M-W-FS

  8. NK2519

    Spirit Airlines

    12:09

    SJC

    3.7h

    17:52

    DFW

    SMTWTFS
    Search

  9. F92882

    Frontier Airlines

    20:19

    DFW

    2.4h

    22:41

    MDW

    S-T-TF-

  10. AA2834

    American Airlines

    14:14

    SJC

    3.6h

    19:49

    DFW

    SMTWT-S
    Search

  11. F92882

    Frontier Airlines

    20:19

    DFW

    2.4h

    22:41

    MDW

    S-T-TF-

  12. AS3429

    Alaska Airlines

    14:36

    SJC

    1.4h

    16:03

    SAN

    SMTWTFS
    Search

  13. F91470

    Frontier Airlines

    20:41

    SAN

    1.6h

    22:15

    LAS

    SMTWTFS

  14. F92330

    Frontier Airlines

    00:59

    LAS

    3.6h

    06:33

    MDW

    SMTWTFS

  15. UA1325

    United Airlines

    16:03

    SJC

    2.6h

    19:38

    DEN

    SMTWTFS
    Search

  16. UA478

    United Airlines

    21:00

    DEN

    2.0h

    21:59

    LAS

    S-TWTFS

  17. F92330

    Frontier Airlines

    00:59

    LAS

    3.6h

    06:33

    MDW

    SMTWTFS

  18. NK222

    Spirit Airlines

    16:44

    SJC

    1.5h

    18:15

    LAS

    SMTWTFS
    Search

  19. F92330

    Frontier Airlines

    00:59

    LAS

    3.6h

    06:33

    MDW

    SMTWTFS

  20. WN2562

    Southwest Airlines

    19:00

    SJC

    1.5h

    20:30

    LAS

    SMTWTFS
    Search

  21. F92330

    Frontier Airlines

    00:59

    LAS

    3.6h

    06:33

    MDW

    SMTWTFS

  22. WN5130

    Southwest Airlines

    19:45

    SJC

    1.4h

    21:10

    LAS

    SMTWT--
    Search

  23. F92330

    Frontier Airlines

    00:59

    LAS

    3.6h

    06:33

    MDW

    SMTWTFS
Find more flights and airlines

SJ International Airport to Midway International Airport Flights Info

Flight distance2,954.2km
Cheapest one-way ticket price€70
Cheapest return ticket price€250

FAQs for SJ International Airport to Midway International Airport Flights

  • How long does it take to fly from SJ International Airport (SJC) to Midway International Airport (MDW)?

    It takes around 4 hours 45 minutes to fly from SJ International Airport (SJC) to SJ International Airport(MDW).

  • How many daily flights are there from SJ International Airport (SJC) to Midway International Airport (MDW)?

    There are around 5 daily flights from SJ International Airport (SJC) to Midway International Airport (MDW).

  • When are flight tickets from SJ International Airport (SJC) to Midway International Airport (MDW) the cheapest?

    Tickets cost around €214 in July, making it the cheapest month to book. SJ International Airport (SJC) to Midway International Airport (MDW) is a popular route, so don't forget to book your tickets in advance.

  • When are flight tickets from SJ International Airport (SJC) to Midway International Airport (MDW) most expensive?

    The route from SJ International Airport (SJC) to Midway International Airport (MDW) is quite popular. Without considering departure times or holidays, tickets cost around €214 in July, the most expensive month to book this route.

  • 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's the closest airport to Midway International Airport (MDW)?

    The closest airport to Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25km.

  • Which airline operates the most direct flights from SJ International Airport (SJC) to Midway International Airport (MDW)?

    Southwest Airlines is a very popular airline operating an average of 300 flights per month.

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