Airlines with flights from San Diego to Chicago

Southwest is the only airline with non-stop flights from San Diego International Airport to Midway International Airport and the flight time is 3 hours and 55 minutes.

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Schedules

Non-stop with Southwest Airlines

  • Total flight time: 3 hours and 55 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 24 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
    Boeing 737-700 (winglets) Passenger/BBJ1
SAN
Direct
MDW
 
Flight
Mon
Sep 30
Tue
Oct 1
Wed
Oct 2
Thu
Oct 3
Fri
Oct 4
Sat
Oct 5
Sun
Oct 6
WN255
06:20
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06:30
06:30
07:50
07:35
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08:45
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11:25
11:40
11:40
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12:20
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14:20
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17:05
17:05
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17:40
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WN2858
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18:45
18:45
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SHOW RETURN SCHEDULE
CHECK PRICES FOR SAN - MDW

The timetable & schedule information was updated at 2024-08-15

Via Las Vegas with Southwest Airlines

  • Total flight time: 5h 40m - 11h 25m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 52 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
    Boeing 737-700 (winglets) Passenger/BBJ1
SAN
 
Via LAS
 
MDW
 
Flight
Mon
Sep 30
Tue
Oct 1
Wed
Oct 2
Thu
Oct 3
Fri
Oct 4
Sat
Oct 5
Sun
Oct 6
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12:10
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15:10
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15:10
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17:25
17:25
----
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17:40
17:40
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR SAN - MDW

The timetable & schedule information was updated at 2024-08-15

Via Denver with Southwest Airlines

  • Total flight time: 5h 20m - 9h 55m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 39 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
    Boeing 737-700 (winglets) Passenger/BBJ1
SAN
 
Via DEN
 
MDW
 
Flight
Mon
Sep 30
Tue
Oct 1
Wed
Oct 2
Thu
Oct 3
Fri
Oct 4
Sat
Oct 5
Sun
Oct 6
WN2714
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06:25
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06:25
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06:25
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06:30
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06:35
06:35
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----
06:40
----
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----
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----
----
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----
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----
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----
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----
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15:10
----
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15:10
----
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WN1564
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WN840
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15:40
----
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----
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15:45
----
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16:05
16:05
----
----
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----
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16:05
----
----
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16:05
----
----
WN803
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----
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16:10
WN803
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----
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WN2828
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----
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----
WN2526
WN2047
16:35
----
----
----
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----
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----
16:35
WN2733
WN1860
16:45
----
----
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WN3541
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17:15
----
----
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17:25
17:25
----
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----
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17:40
17:40
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR SAN - MDW

The timetable & schedule information was updated at 2024-08-15

Via Phoenix with Southwest Airlines

  • Total flight time: 5h 15m - 10h 15m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 39 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
    Boeing 737-700 (winglets) Passenger/BBJ1
SAN
 
Via PHX
 
MDW
 
Flight
Mon
Sep 30
Tue
Oct 1
Wed
Oct 2
Thu
Oct 3
Fri
Oct 4
Sat
Oct 5
Sun
Oct 6
WN2714
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06:25
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06:25
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06:25
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----
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WN687
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----
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----
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----
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WN503
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----
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WN957
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07:20
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WN3435
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----
WN2474
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----
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----
WN1959
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----
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WN1959
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WN785
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08:00
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----
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WN1891
WN2759
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----
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----
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WN3845
08:10
----
----
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----
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----
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08:10
----
----
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----
WN2955
WN3023
08:10
----
----
----
----
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----
WN791
WN2574
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----
----
----
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----
08:15
WN4276
WN2780
----
----
----
----
----
08:15
----
WN469
WN296
08:20
----
----
----
----
----
----
WN469
WN597
08:20
----
----
----
----
----
----
WN469
WN4552
08:20
----
----
----
----
----
----
WN3370
WN3023
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08:25
08:25
----
----
----
----
WN1647
WN2969
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----
----
----
----
08:25
----
WN4389
WN4727
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08:30
----
----
----
----
WN1336
WN597
08:30
----
----
----
----
----
----
WN1336
WN1515
08:30
----
----
----
----
----
----
WN1453
WN1980
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----
----
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08:35
----
----
WN2285
WN279
08:35
----
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----
----
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----
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WN3659
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08:40
WN1059
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WN1553
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08:45
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15:10
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15:10
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----
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15:45
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16:05
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16:05
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----
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----
WN2526
WN2047
16:35
----
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WN2733
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16:45
----
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WN2305
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17:25
----
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17:40
17:40
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----
SHOW RETURN SCHEDULE
CHECK PRICES FOR SAN - MDW

The timetable & schedule information was updated at 2024-08-15

Via Dallas with Southwest Airlines

  • Total flight time: 5h 50m - 11h 20m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 22 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
    Boeing 737-700 (winglets) Passenger/BBJ1
SAN
 
Via DAL
 
MDW
 
Flight
Mon
Sep 30
Tue
Oct 1
Wed
Oct 2
Thu
Oct 3
Fri
Oct 4
Sat
Oct 5
Sun
Oct 6
WN2714
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06:25
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06:25
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06:25
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----
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----
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WN687
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----
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WN341
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07:00
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07:00
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07:00
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WN4344
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07:05
----
----
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----
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WN1478
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----
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----
----
WN1478
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----
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WN503
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07:20
07:20
----
----
WN957
WN279
07:20
----
----
----
----
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----
WN3435
WN2969
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----
07:25
----
WN2474
WN1223
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07:40
----
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----
07:40
----
WN1959
WN423
----
07:45
07:45
----
----
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----
WN1959
WN2166
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07:45
07:45
----
----
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----
WN1764
WN582
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----
07:45
07:45
----
----
WN2876
WN3705
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07:55
WN2876
WN3222
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07:55
WN785
WN2679
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----
08:00
08:00
----
----
WN785
WN1781
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----
08:00
08:00
----
----
WN1490
WN3786
----
----
----
----
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----
08:10
WN1891
WN2759
----
----
----
08:10
08:10
----
----
WN2955
WN3845
08:10
----
----
----
----
----
----
WN3903
WN1379
----
08:10
08:10
----
----
----
----
WN2955
WN3023
08:10
----
----
----
----
----
----
WN791
WN2574
----
----
----
----
----
----
08:15
WN4276
WN2780
----
----
----
----
----
08:15
----
WN469
WN296
08:20
----
----
----
----
----
----
WN469
WN597
08:20
----
----
----
----
----
----
WN469
WN4552
08:20
----
----
----
----
----
----
WN3370
WN3023
----
08:25
08:25
----
----
----
----
WN1647
WN2969
----
----
----
----
----
08:25
----
WN4389
WN4727
----
08:30
08:30
----
----
----
----
WN1336
WN597
08:30
----
----
----
----
----
----
WN1336
WN1515
08:30
----
----
----
----
----
----
WN1453
WN1980
----
----
----
08:35
08:35
----
----
WN2285
WN279
08:35
----
----
----
----
----
----
WN1050
WN3659
----
----
----
----
----
----
08:40
WN1059
WN3093
----
----
----
----
----
08:40
----
WN1050
WN3705
----
----
----
----
----
----
08:40
WN1050
WN3222
----
----
----
----
----
----
08:40
WN1050
WN2969
----
----
----
----
----
----
08:40
WN1553
WN1249
08:45
----
----
----
----
----
----
WN787
WN3783
----
----
----
----
----
09:10
----
WN787
WN1223
----
----
----
----
----
09:10
----
WN3658
WN1200
----
09:15
09:15
----
----
----
----
WN2211
WN1385
09:15
----
----
----
----
----
----
WN910
WN2759
----
----
----
09:15
09:15
----
----
WN910
WN2217
----
----
----
09:15
09:15
----
----
WN910
WN3660
----
----
----
09:15
09:15
----
----
WN2211
WN3023
09:15
----
----
----
----
----
----
WN2367
WN4234
----
----
----
----
----
----
09:20
WN2367
WN2574
----
----
----
----
----
----
09:20
WN1088
WN1935
----
09:35
09:35
----
----
----
----
WN1088
WN2728
----
09:35
09:35
----
----
----
----
WN4103
WN784
----
----
----
----
----
----
09:40
WN4300
WN4573
----
----
----
09:40
09:40
----
----
WN1360
WN3705
----
----
----
----
----
----
09:45
WN1360
WN3222
----
----
----
----
----
----
09:45
WN1360
WN3408
----
----
----
----
----
----
09:45
WN1360
WN2969
----
----
----
----
----
----
09:45
WN3254
WN2492
10:10
----
----
----
----
----
----
WN4910
WN1781
----
----
----
10:10
10:10
----
----
WN4910
WN2375
----
----
----
10:10
10:10
----
----
WN4910
WN3336
----
----
----
10:10
10:10
----
----
WN2086
WN573
----
----
----
10:15
10:15
----
----
WN2982
WN2212
----
10:20
10:20
----
----
----
----
WN2571
WN3786
----
----
----
----
----
10:20
----
WN1059
WN2088
10:30
----
----
----
----
----
----
WN1059
WN3628
10:30
----
----
----
----
----
----
WN543
WN1223
----
----
----
10:35
10:35
----
----
WN4395
WN1515
----
10:35
10:35
----
----
----
----
WN1546
WN3408
----
----
----
----
----
10:35
----
WN543
WN4051
----
----
----
10:35
10:35
----
----
WN4142
WN3408
----
----
----
10:40
10:40
----
----
WN4142
WN2217
----
----
----
10:40
10:40
----
----
WN597
WN1515
10:40
----
----
----
----
----
----
WN2524
WN3408
----
----
----
----
----
----
10:45
WN979
WN1594
10:50
----
----
----
----
----
----
WN979
WN2088
10:50
----
----
----
----
----
----
WN2048
WN2807
----
----
----
10:55
10:55
----
----
WN3903
WN3173
11:00
----
----
----
----
----
----
WN3236
WN4132
----
----
----
11:05
11:05
----
----
WN3536
WN1935
----
11:05
11:05
----
----
----
----
WN3236
WN120
----
----
----
11:05
11:05
----
----
WN4285
WN240
----
----
----
----
----
11:05
----
WN2502
WN2728
----
11:05
11:05
----
----
----
----
WN3863
WN747
----
----
----
----
----
11:05
----
WN429
WN3555
----
----
----
11:05
11:05
----
----
WN3536
WN671
----
11:05
11:05
----
----
----
----
WN3744
WN733
----
----
----
11:15
11:15
----
----
WN3265
WN3506
----
----
----
----
----
----
11:15
WN3265
WN488
----
----
----
----
----
----
11:15
WN3265
WN679
----
----
----
----
----
----
11:15
WN2714
WN1563
----
----
----
----
----
----
11:20
WN2714
WN2014
----
----
----
----
----
----
11:20
WN2714
WN3680
----
----
----
----
----
----
11:20
WN2297
WN3093
----
----
----
----
----
----
11:30
WN330
WN2791
----
11:30
11:30
----
----
----
----
WN1950
WN1223
----
----
----
----
----
11:35
----
WN3654
WN3628
11:45
----
----
----
----
----
----
WN1576
WN2806
12:10
----
----
----
----
----
----
WN2793
WN2602
----
----
----
12:10
12:10
----
----
WN1576
WN3534
12:10
----
----
----
----
----
----
WN2793
WN2809
----
----
----
12:10
12:10
----
----
WN995
WN4132
----
----
----
12:15
12:15
----
----
WN429
WN3680
----
----
----
----
----
12:15
----
WN3412
WN671
----
12:20
12:20
----
----
----
----
WN456
WN2088
12:25
----
----
----
----
----
----
WN2076
WN3486
----
12:30
12:30
----
----
----
----
WN2076
WN1187
----
12:30
12:30
----
----
----
----
WN702
WN262
----
----
----
12:30
12:30
----
----
WN2835
WN3534
----
12:40
12:40
----
----
----
----
WN4924
WN4763
----
----
----
12:40
12:40
----
----
WN2835
WN3486
----
12:40
12:40
----
----
----
----
WN608
WN694
12:45
----
----
----
----
----
----
WN2947
WN4187
----
----
----
----
----
----
12:50
WN909
WN2707
----
13:00
13:00
----
----
----
----
WN687
WN3486
----
13:05
13:05
----
----
----
----
WN3527
WN2707
13:10
----
----
----
----
----
----
WN1252
WN240
----
----
----
----
----
----
13:10
WN1762
WN3766
----
13:25
13:25
----
----
----
----
WN712
WN674
13:25
----
----
----
----
----
----
WN4636
WN733
----
----
----
13:30
13:30
----
----
WN3490
WN240
----
----
----
----
----
13:35
----
WN1400
WN694
13:40
----
----
----
----
----
----
WN1400
WN1881
13:40
----
----
----
----
----
----
WN2571
WN4510
----
----
----
13:45
13:45
----
----
WN2012
WN823
----
13:50
13:50
----
----
----
----
WN3034
WN342
----
----
----
14:10
14:10
14:30
13:50
WN4538
WN3671
----
----
----
13:55
13:55
----
----
WN4293
WN240
----
----
----
----
----
----
14:00
WN644
WN3368
----
----
----
----
----
----
14:10
WN3034
WN262
----
----
----
14:10
14:10
----
----
WN1655
WN845
----
14:15
14:15
----
----
----
----
WN1655
WN555
----
14:15
14:15
----
----
----
----
WN3269
WN2429
----
----
----
----
----
----
14:35
WN3269
WN240
----
----
----
----
----
----
14:35
WN758
WN3486
----
14:40
14:40
----
----
----
----
WN1198
WN1575
14:55
----
----
----
----
----
----
WN4285
WN1498
----
----
----
14:55
14:55
----
----
WN991
WN2006
----
----
----
15:00
15:00
----
----
WN2053
WN2805
----
15:00
15:00
----
----
----
----
WN3252
WN3368
----
----
----
15:05
15:05
----
----
WN1180
WN2715
----
----
----
----
----
----
15:05
WN1180
WN4569
----
----
----
----
----
----
15:05
WN3252
WN3671
----
----
----
15:05
15:05
----
----
WN3536
WN2047
15:10
----
----
----
----
----
----
WN3536
WN1881
15:10
----
----
----
----
----
----
WN1564
WN3867
----
----
----
----
----
----
15:20
WN1564
WN342
----
----
----
----
----
----
15:20
WN840
WN555
----
15:40
15:40
----
----
----
----
WN2787
WN342
----
----
----
----
----
15:45
----
WN2053
WN1860
15:45
----
----
----
----
----
----
WN2065
WN2805
----
16:05
16:05
----
----
----
----
WN2557
WN1763
----
----
----
16:05
16:05
----
----
WN2557
WN4898
----
----
----
16:05
16:05
----
----
WN803
WN5016
----
----
----
----
----
----
16:10
WN803
WN3368
----
----
----
----
----
----
16:10
WN2828
WN3368
----
----
----
----
----
16:10
----
WN2526
WN2047
16:35
----
----
----
----
----
----
WN3179
WN240
----
----
----
----
----
----
16:35
WN2733
WN1860
16:45
----
----
----
----
----
----
WN3541
WN2305
----
----
----
----
----
----
17:05
WN3541
WN3867
----
----
----
----
----
----
17:05
WN1576
WN1763
----
----
----
17:15
17:15
----
----
WN792
WN981
----
----
----
17:25
17:25
----
----
WN3784
WN1498
----
----
----
17:40
17:40
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR SAN - MDW

The timetable & schedule information was updated at 2024-08-15

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