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

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

  • One way
  • Round-trip
sortSort by: Lowest Price
  • Sort by: Lowest Price
  • Sort by: Earliest Flight
      • SAN19:09
        12h 13m
        1 stop
        MDW09:22
        San Diego - Chicago|Tue, May 7|Frontier Airlines
        $43$77
        45% OFF
        45% OFF
        $77$43
      • SAN08:04
        7h 8m
        1 stop
        MDW17:12
        San Diego - Chicago|Tue, May 21|Frontier Airlines
        $45$77
        42% OFF
        42% OFF
        $77$45
      • SAN20:21
        7h 29m
        1 stop
        MDW05:50
        San Diego - Chicago|Sat, May 18|Frontier Airlines
        $46$77
        41% OFF
        41% OFF
        $77$46
      • SAN21:32
        12h 4m
        1 stop
        MDW11:36
        San Diego - Chicago|Wed, May 8|Frontier Airlines
        $48
        $48
      • SAN08:00
        12h 5m
        1 stop
        MDW22:05
        San Diego - Chicago|Tue, May 14|Frontier Airlines
        $49
        $49
      • SAN16:07
        14h 29m
        1 stop
        MDW08:36
        San Diego - Chicago|Wed, May 1|Frontier Airlines
        $53
        $53
      • SAN20:21
        7h 29m
        1 stop
        MDW05:50
        San Diego - Chicago|Fri, May 17|Frontier Airlines
        $54
        $54
      • SAN21:32
        12h 4m
        1 stop
        MDW11:36
        San Diego - Chicago|Fri, May 10|Frontier Airlines
        $61
        $61
      • SAN11:04
        16h 46m
        1 stop
        MDW05:50
        San Diego - Chicago|Mon, Jun 3|Frontier Airlines
        $62
        $62
      • SAN18:19
        9h 31m
        1 stop
        MDW05:50
        San Diego - Chicago|Sun, May 19|Frontier Airlines
        $63
        $63
      • SAN13:00
        3h 5m
        Direct
        MDW14:00
        San Diego - Chicago|Wed, May 8|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 Diego International Airport to Midway International Airport

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

Frontier Airlines
From $43
Spirit Airlines
From $69
Alaska Airlines
From $88
Southwest Airlines
From $98
Delta Air Lines
From $110
American Airlines
From $112
United Airlines
From $191
ANA airlines
Find more flights and airlines

Find Cheaper Flights from San Diego to Chicago

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

  • Cheapest
    Frontier Airlines
    SAN
    16:07
    6h 49m
    1 transfer
    ORD
    00:56
    San Diego International Airport - O'Hare International Airport
    Wed, May 8Frontier Airlines
    $35
  • Frontier Airlines
    SAN
    16:07
    6h 49m
    1 transfer
    ORD
    00:56
    San Diego International Airport - O'Hare International Airport
    Wed, May 8Frontier Airlines
    $35
    Find More Flights
Flight Schedule from San Diego International Airport to Midway International Airport

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

Flight info.
Departure
Arrival
Weekly Schedule

  1. F92818

    Frontier Airlines

    08:01

    SAN

    2.4h

    11:27

    DEN

    SMTWTFS
    Search

  2. F92946

    Frontier Airlines

    15:46

    DEN

    2.4h

    19:11

    MDW

    -M-W--S

  3. F91426

    Frontier Airlines

    08:19

    SAN

    3.2h

    13:29

    DFW

    SMTWTFS
    Search

  4. F94298

    Frontier Airlines

    20:21

    DFW

    2.4h

    22:46

    MDW

    ----TF-

  5. F91326

    Frontier Airlines

    08:21

    SAN

    1.4h

    09:43

    LAS

    SMTWTFS
    Search

  6. F92330

    Frontier Airlines

    23:48

    LAS

    3.5h

    05:21

    MDW

    SMTWTFS

  7. F94928

    Frontier Airlines

    10:08

    SAN

    2.5h

    13:36

    DEN

    SMTWTFS
    Search

  8. F92946

    Frontier Airlines

    15:46

    DEN

    2.4h

    19:11

    MDW

    -M-W--S

  9. F94990

    Frontier Airlines

    15:22

    SAN

    2.4h

    18:48

    DEN

    S--W-FS
    Search

  10. F92210

    Frontier Airlines

    07:44

    DEN

    2.4h

    11:08

    MDW

    SMTWTFS

  11. F94990

    Frontier Airlines

    15:22

    SAN

    2.4h

    18:48

    DEN

    S--W-FS
    Search

  12. F92946

    Frontier Airlines

    15:46

    DEN

    2.4h

    19:11

    MDW

    -M-W--S

  13. F94988

    Frontier Airlines

    18:50

    SAN

    2.5h

    22:20

    DEN

    --T----
    Search

  14. F92210

    Frontier Airlines

    07:44

    DEN

    2.4h

    11:08

    MDW

    SMTWTFS

  15. F94618

    Frontier Airlines

    19:54

    SAN

    3.0h

    00:57

    DFW

    -M-W-F-
    Search

  16. F93000

    Frontier Airlines

    13:31

    DFW

    2.4h

    15:52

    MDW

    SMTW--S

  17. F91470

    Frontier Airlines

    20:21

    SAN

    1.5h

    21:53

    LAS

    SMTWTFS
    Search

  18. F92330

    Frontier Airlines

    23:48

    LAS

    3.5h

    05:21

    MDW

    SMTWTFS

  19. NK744

    Spirit Airlines

    22:38

    SAN

    1.4h

    00:03

    LAS

    SMTWT-S
    Search

  20. NK1270

    Spirit Airlines

    13:05

    LAS

    2.8h

    17:55

    DFW

    SMTW-FS

  21. F93534

    Frontier Airlines

    14:59

    DFW

    2.4h

    17:23

    MDW

    SMTWTFS
Find more flights and airlines

San Diego International Airport to Midway International Airport Flights Info

Flight distance2,780.79km
Cheapest one-way ticket price$42
Cheapest return ticket price$87

FAQs for San Diego International Airport to Midway International Airport Flights

  • How long is a flight from San Diego International Airport to Midway International Airport?

    It takes around 3 hours 55 minutes to fly from San Diego International Airport (SAN) to Midway International Airport (MDW).

  • How many daily flights are there from San Diego International Airport (SAN) to Midway International Airport (MDW)?

    There are around 2 daily flights from San Diego International Airport (SAN) to Midway International Airport (MDW).

  • When are flight tickets from San Diego International Airport (SAN) to Midway International Airport (MDW) the cheapest?

    Tickets cost around $400 in April, making it the cheapest month to book. San Diego International Airport (SAN) to Midway International Airport (MDW) is a popular route, so don't forget to book your tickets in advance.

  • When are flight tickets from San Diego International Airport (SAN) to Midway International Airport (MDW) most expensive?

    The route from San Diego International Airport (SAN) to Midway International Airport (MDW) is quite popular. Without considering departure times or holidays, tickets cost around $400 in April, the most expensive month to book this route.

  • What time does the earliest flight from San Diego International Airport to Midway International Airport depart?

    The earliest flight departs from San Diego International Airport (SAN) at 06:30 and arrives in Midway International Airport (MDW) at 14:35.

  • What time does the latest flight from San Diego International Airport to Midway International Airport depart?

    The latest flight departs from San Diego International Airport (SAN) at 20:00 and arrives in Midway International Airport (MDW) at 01:50.

  • 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'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 San Diego International Airport (SAN) to Midway International Airport (MDW)?

    Southwest Airlines is a very popular airline operating an average of 600 flights per month.

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