Find Deals on Flights from Chicago Midway to San Diego (MDW - SAN)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youth
12-17
Child
2-11
Seat Infant
under 2
Lap Infant
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Chicago Midway to San Diego

(Round-trip)
Depart: Sat Aug 29 2015 Return: Wed Sep 9 2015 Trip spans 12 days
Sun Country Air
Sun Country Air
MDW
4:00a
SAN
10:07a
6h 07m
1 stop
SAN
9:00a
MDW
2:45p
5h 45m
1 stop
Depart: Sun Aug 30 2015 Return: Wed Sep 9 2015 Trip spans 11 days
Sun Country Air
Sun Country Air
MDW
4:00a
SAN
10:07a
6h 07m
1 stop
SAN
9:00a
MDW
2:45p
5h 45m
1 stop
Depart: Tue Sep 1 2015 Return: Wed Sep 9 2015 Trip spans 9 days
Sun Country Air
Sun Country Air
MDW
4:00a
SAN
10:07a
6h 07m
1 stop
SAN
9:00a
MDW
2:45p
5h 45m
1 stop
Depart: Thu Sep 3 2015 Return: Wed Sep 9 2015 Trip spans 7 days
Sun Country Air
Sun Country Air
MDW
4:00a
SAN
10:07a
6h 07m
1 stop
SAN
9:00a
MDW
2:45p
5h 45m
1 stop
Depart: Mon Aug 31 2015 Return: Thu Sep 10 2015 Trip spans 11 days
Sun Country Air
Sun Country Air
MDW
4:00a
SAN
10:07a
6h 07m
1 stop
SAN
9:00a
MDW
2:45p
5h 45m
1 stop
Depart: Thu Sep 10 2015 Return: Fri Sep 11 2015 Trip spans 2 days
Sun Country Air
Sun Country Air
MDW
4:00a
SAN
10:07a
6h 07m
1 stop
SAN
9:00a
MDW
2:45p
5h 45m
1 stop
Depart: Fri Sep 4 2015 Return: Sat Sep 5 2015 Trip spans 2 days
Delta
Delta
MDW
12:35p
SAN
8:03p
7h 28m
1 stop
SAN
8:30a
MDW
3:08p
6h 38m
1 stop
Depart: Sat Sep 5 2015 Return: Sun Sep 6 2015 Trip spans 2 days
Delta
Delta
MDW
11:11a
SAN
5:22p
6h 11m
1 stop
SAN
2:25a
MDW
10:39a
8h 14m
1 stop
Depart: Wed Sep 9 2015 Return: Thu Sep 10 2015 Trip spans 2 days
Delta
Delta
MDW
11:20a
SAN
7:08p
7h 48m
1 stop
SAN
6:47a
MDW
4:07p
9h 20m
1 stop
Depart: Fri Sep 11 2015 Return: Sat Sep 12 2015 Trip spans 2 days
Delta
Delta
MDW
5:02a
SAN
11:18a
6h 16m
1 stop
SAN
3:00a
MDW
9:53a
6h 53m
1 stop
Depart: Sat Sep 12 2015 Return: Sun Sep 13 2015 Trip spans 2 days
Delta
Delta
MDW
8:29a
SAN
3:40p
7h 11m
1 stop
SAN
3:00a
MDW
11:54a
8h 54m
1 stop
Depart: Tue Sep 15 2015 Return: Wed Sep 16 2015 Trip spans 2 days
Delta
Delta
MDW
11:20a
SAN
7:08p
7h 48m
1 stop
SAN
2:25a
MDW
10:39a
8h 14m
1 stop
Depart: Fri Sep 18 2015 Return: Tue Sep 22 2015 Trip spans 5 days
Delta
Delta
MDW
2:00a
SAN
9:19a
7h 19m
1 stop
SAN
2:25a
MDW
10:39a
8h 14m
1 stop
Depart: Sat Sep 19 2015 Return: Tue Sep 22 2015 Trip spans 4 days
Delta
Delta
MDW
11:11a
SAN
5:22p
6h 11m
1 stop
SAN
2:25a
MDW
8:41a
6h 16m
1 stop
Depart: Tue Sep 22 2015 Return: Fri Sep 25 2015 Trip spans 4 days
Delta
Delta
MDW
9:50a
SAN
7:08p
9h 18m
1 stop
SAN
6:30p
MDW
3:12a
8h 42m
1 stop
Depart: Wed Sep 23 2015 Return: Sat Sep 26 2015 Trip spans 4 days
Delta
Delta
MDW
5:02a
SAN
11:18a
6h 16m
1 stop
SAN
2:25a
MDW
8:40a
6h 15m
1 stop
Depart: Thu Sep 24 2015 Return: Mon Sep 28 2015 Trip spans 5 days
Delta
Delta
MDW
12:35p
SAN
8:03p
7h 28m
1 stop
SAN
6:30p
MDW
3:18a
8h 48m
1 stop
Depart: Sat Sep 26 2015 Return: Mon Sep 28 2015 Trip spans 3 days
Delta
Delta
MDW
12:35p
SAN
8:07p
7h 32m
1 stop
SAN
6:30p
MDW
3:18a
8h 48m
1 stop
Depart: Tue Sep 29 2015 Return: Fri Oct 2 2015 Trip spans 4 days
Delta
Delta
MDW
2:35a
SAN
9:06a
6h 31m
1 stop
SAN
7:35a
MDW
2:29p
6h 54m
1 stop
Depart: Sun Oct 18 2015 Return: Fri Oct 23 2015 Trip spans 6 days
Southwest
Southwest
MDW
4:25a
SAN
8:55a
4h 30m
nonstop
SAN
7:20a
MDW
2:50p
7h 30m
1 stop
Select an airline:  Southwest
Direct flights MDW to SAN on Southwest
Flight # Depart MDW Arrive SAN Sun Mon Tue Wed Thu Fri Sat Valid Between
1543 8:25 am 10:55 am Sep 27 - Oct 25
1543 8:25 am 10:55 am Sep 28 - Oct 30
1543 8:25 am 10:50 am Aug 30 - Sep 4
1543 8:25 am 10:50 am Sep 7 - Sep 25
3225 9:20 am 11:50 am Oct 3 - Oct 31
5690 9:20 am 11:45 am Sep 5 - Sep 5
780 9:20 am 11:45 am Sep 12 - Sep 26
1023 11:25 am 1:50 pm Sep 27 - Oct 25
3057 11:25 am 1:40 pm Aug 30 - Sep 4
3057 11:25 am 1:50 pm Sep 28 - Oct 30
3057 11:25 am 1:40 pm Sep 7 - Sep 7
3057 11:25 am 1:40 pm Sep 8 - Sep 25
5404 11:25 am 1:50 pm Sep 6 - Sep 6
4435 1:20 pm 3:35 pm Sep 12 - Sep 26
4435 1:20 pm 3:40 pm Oct 3 - Oct 31
1288 3:10 pm 5:30 pm Sep 6 - Sep 6
288 3:10 pm 5:25 pm Aug 30 - Sep 4
288 3:10 pm 5:30 pm Sep 27 - Oct 30
288 3:10 pm 5:25 pm Sep 7 - Sep 25
5657 4:10 pm 6:25 pm Sep 5 - Sep 5
748 4:10 pm 6:25 pm Sep 12 - Sep 26
722 4:15 pm 6:35 pm Oct 3 - Oct 24
5132 6:25 pm 8:40 pm Sep 5 - Sep 5
1330 7:35 pm 9:55 pm Sep 6 - Sep 7
1676 7:35 pm 9:55 pm Sep 27 - Oct 30
3420 7:35 pm 9:55 pm Oct 3 - Oct 24
3420 7:40 pm 10:00 pm Sep 12 - Sep 26
1676 7:45 pm 10:05 pm Aug 30 - Sep 4
1676 7:45 pm 10:05 pm Sep 8 - Sep 25
Airports
Origin

Chicago
$246
Destination

San Diego
$246