App
Help
USD
Search Bookings
Trip.com
>
Flights
>
Flights to Chicago
>
San Jose to Chicago flight
>
San Jose to Midway International Airport flight
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

Cheap Flights from San Jose to Midway International Airport

  • One way
  • Round-trip
sortSort by: Lowest Price
  • Sort by: Lowest Price
  • Sort by: Earliest Flight
      • SJC08:05
        12h
        2 stops
        MDW22:05
        San Jose - Chicago|Tue, May 7|Spirit Airlines
        US$92US$145
        37% OFF
        37% OFF
        US$145US$92
      • SJC08:05
        25h 31m
        1 stop
        MDW11:36
        San Jose - Chicago|Mon, Apr 29|Spirit Airlines
        US$93US$145
        36% OFF
        36% OFF
        US$145US$93
      • SJC08:05
        25h 31m
        1 stop
        MDW11:36
        San Jose - Chicago|Wed, May 1|Spirit Airlines
        US$94US$145
        36% OFF
        36% OFF
        US$145US$94
      • SJC07:00
        26h 36m
        1 stop
        MDW11:36
        San Jose - Chicago|Thu, May 2|Spirit Airlines
        US$94
        US$94
      • SJC08:05
        25h 31m
        1 stop
        MDW11:36
        San Jose - Chicago|Mon, May 6|Spirit Airlines
        US$97
        US$97
      • SJC17:45
        12h 36m
        1 stop
        MDW08:21
        San Jose - Chicago|Wed, May 8|Spirit Airlines
        US$102
        US$102
      • SJC10:20
        17h 30m
        2 stops
        MDW05:50
        San Jose - Chicago|Wed, May 15|Alaska Airlines
        US$112
        US$112
      • SJC06:15
        11h 40m
        2 stops
        MDW19:55
        San Jose - Chicago|Tue, May 21|Alaska Airlines
        US$113
        US$113
      • SJC16:40
        11h 10m
        1 stop
        MDW05:50
        San Jose - Chicago|Wed, May 29|Spirit Airlines
        US$114
        US$114
      • SJC06:10
        7h 51m
        1 stop
        MDW16:01
        San Jose - Chicago|Tue, May 14|American Airlines
        US$117
        US$117
      • SJC13:00
        3h 5m
        Direct
        MDW14:00
        San Jose - Chicago|Sat, May 4|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 San Jose to Midway International Airport
Spirit Airlines
From US$92
Alaska Airlines
From US$112
American Airlines
From US$117
United Airlines
From US$130
Delta Air Lines
From US$131
Southwest Airlines
From US$151
ANA airlines
Find more flights and airlines

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

  • 1.67 km from downtown San Jose
    SJ International Airport
    Tickets From
    US$92
Flight Schedule from San Jose to Midway International Airport
Flight info.
Departure
Arrival
Weekly Schedule

  1. AA1019

    American Airlines

    06:10

    SJC

    3.7h

    11:54

    DFW

    SMTWTFS
    Search

  2. F93000

    Frontier Airlines

    18:40

    DFW

    2.4h

    21:02

    MDW

    SMTW--S

  3. AA1019

    American Airlines

    06:10

    SJC

    3.7h

    11:54

    DFW

    SMTWTFS
    Search

  4. F93534

    Frontier Airlines

    13:51

    DFW

    2.3h

    16:08

    MDW

    SMTWTFS

  5. AS3458

    Alaska Airlines

    06:15

    SJC

    1.5h

    07:45

    SAN

    S--WTFS
    Search

  6. F91426

    Frontier Airlines

    08:28

    SAN

    3.1h

    13:32

    DFW

    SMTWTFS

  7. F94298

    Frontier Airlines

    20:21

    DFW

    2.4h

    22:46

    MDW

    ----TF-

  8. NK2203

    Spirit Airlines

    08:05

    SJC

    1.5h

    09:33

    LAS

    SMTWTFS
    Search

  9. F93844

    Frontier Airlines

    15:07

    LAS

    2.1h

    18:11

    DEN

    SMTWT-S

  10. F92946

    Frontier Airlines

    13:52

    DEN

    2.4h

    17:14

    MDW

    -M-W--S

  11. UA1802

    United Airlines

    08:25

    SJC

    2.6h

    12:03

    DEN

    SMTWTFS
    Search

  12. F92946

    Frontier Airlines

    13:52

    DEN

    2.4h

    17:14

    MDW

    -M-W--S

  13. UA1802

    United Airlines

    08:25

    SJC

    2.6h

    12:03

    DEN

    SMTWTFS
    Search

  14. F92210

    Frontier Airlines

    07:58

    DEN

    2.4h

    11:20

    MDW

    SMTWTFS

  15. WN4152

    Southwest Airlines

    09:55

    SJC

    1.4h

    11:20

    SAN

    SMTWTFS
    Search

  16. WN1379

    Southwest Airlines

    17:45

    SAN

    3.8h

    23:35

    MDW

    SMTWT-S

  17. UA1104

    United Airlines

    10:42

    SJC

    2.6h

    14:20

    DEN

    -MTWTFS
    Search

  18. F92946

    Frontier Airlines

    13:52

    DEN

    2.4h

    17:14

    MDW

    -M-W--S

  19. NK2519

    Spirit Airlines

    12:15

    SJC

    3.6h

    17:50

    DFW

    S--WT-S
    Search

  20. F93000

    Frontier Airlines

    18:40

    DFW

    2.4h

    21:02

    MDW

    SMTW--S

  21. NK2523

    Spirit Airlines

    21:46

    SJC

    1.4h

    23:13

    LAS

    SMTWTFS
    Search

  22. NK2920

    Spirit Airlines

    07:00

    LAS

    2.8h

    11:45

    DFW

    SMTWTFS

  23. F94298

    Frontier Airlines

    20:21

    DFW

    2.4h

    22:46

    MDW

    ----TF-
Find more flights and airlines

Flight Info of Flights from San Jose to Midway International Airport

Cheapest round-trip ticket price

$224

Cheapest nonstop flight price

$50

Off-season for travel

February

Peak season for travel

October

FAQs for San Jose to Midway International Airport Flights

  • When are flight tickets from San Jose (SJC) 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 (SJC) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around $407.

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

    It takes around 4 hours 44 minutes to fly from San Jose (SJC) 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. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14km. It takes about 30 minutes by taxi.

  • What are the most popular airlines that fly from San Jose (SJC) to Chicago (CHI)?

    Airlines with flights from San Jose (SJC) to Chicago (CHI): Southwest Airlines and United Airlines.

Contact Us

About

Other Services

Payment Methods
Our Partners
Copyright © 2024 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd.