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

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago Midway to San Diego

(Round-trip)
Depart: Thu May 28 2015 Return: Fri May 29 2015 Trip spans 2 days
Sun Country Air
Sun Country Air
MDW
4:00a
SAN
10:10a
6h 10m
1 stop
SAN
9:00a
MDW
2:45p
5h 45m
1 stop
Depart: Tue May 5 2015 Return: Mon May 11 2015 Trip spans 7 days
Sun Country Air
Sun Country Air
MDW
4:00a
SAN
10:10a
6h 10m
1 stop
SAN
9:00a
MDW
2:45p
5h 45m
1 stop
Depart: Sat May 16 2015 Return: Mon May 18 2015 Trip spans 3 days
Delta
Delta
MDW
12:30p
SAN
7:54p
7h 24m
1 stop
SAN
6:30p
MDW
3:23a
8h 53m
1 stop
Depart: Wed May 27 2015 Return: Fri May 29 2015 Trip spans 3 days
Delta
Delta
MDW
2:45a
SAN
10:53a
8h 08m
1 stop
SAN
6:47a
MDW
1:59p
7h 12m
1 stop
Depart: Fri May 29 2015 Return: Sat May 30 2015 Trip spans 2 days
Delta
Delta
MDW
5:07a
SAN
10:53a
5h 46m
1 stop
SAN
2:25a
MDW
8:41a
6h 16m
1 stop
Depart: Sat May 30 2015 Return: Mon Jun 1 2015 Trip spans 3 days
Delta
Delta
MDW
5:56a
SAN
3:05p
9h 09m
1 stop
SAN
6:30p
MDW
3:23a
8h 53m
1 stop
Depart: Sun May 31 2015 Return: Tue Jun 2 2015 Trip spans 3 days
Delta
Delta
MDW
2:45a
SAN
9:19a
6h 34m
1 stop
SAN
6:47a
MDW
4:10p
9h 23m
1 stop
Depart: Mon Jun 1 2015 Return: Wed Jun 3 2015 Trip spans 3 days
Delta
Delta
MDW
5:07a
SAN
10:53a
5h 46m
1 stop
SAN
8:30a
MDW
3:06p
6h 36m
1 stop
Depart: Tue Jun 2 2015 Return: Mon Jun 8 2015 Trip spans 7 days
Delta
Delta
MDW
2:45a
SAN
9:19a
6h 34m
1 stop
SAN
2:15a
MDW
12:53p
10h 38m
1 stop
Depart: Wed Jun 3 2015 Return: Mon Jun 8 2015 Trip spans 6 days
Delta
Delta
MDW
3:27p
SAN
9:39p
6h 12m
1 stop
SAN
6:45p
MDW
1:56a
7h 11m
1 stop
Depart: Thu Jun 4 2015 Return: Tue Jun 9 2015 Trip spans 6 days
Delta
Delta
MDW
8:30a
SAN
3:33p
7h 03m
1 stop
SAN
6:45p
MDW
1:56a
7h 11m
1 stop
Depart: Fri Jun 5 2015 Return: Sat Jun 6 2015 Trip spans 2 days
Delta
Delta
MDW
3:31p
SAN
9:41p
6h 10m
1 stop
SAN
7:19a
MDW
2:12p
6h 53m
1 stop
Depart: Sat Jun 6 2015 Return: Mon Jun 8 2015 Trip spans 3 days
Delta
Delta
MDW
2:05p
SAN
9:32p
7h 27m
1 stop
SAN
2:15a
MDW
12:53p
10h 38m
1 stop
Depart: Wed Jun 10 2015 Return: Sat Jun 13 2015 Trip spans 4 days
Delta
Delta
MDW
5:47a
SAN
3:05p
9h 18m
1 stop
SAN
2:25a
MDW
10:36a
8h 11m
1 stop
Depart: Fri Jun 12 2015 Return: Sat Jun 13 2015 Trip spans 2 days
Delta
Delta
MDW
3:31p
SAN
9:41p
6h 10m
1 stop
SAN
2:25a
MDW
8:33a
6h 08m
1 stop
Depart: Wed Jun 17 2015 Return: Mon Jun 22 2015 Trip spans 6 days
Delta
Delta
MDW
5:08a
SAN
11:25a
6h 17m
1 stop
SAN
6:45p
MDW
1:56a
7h 11m
1 stop
Depart: Fri Jun 19 2015 Return: Mon Jun 22 2015 Trip spans 4 days
Delta
Delta
MDW
5:08a
SAN
11:25a
6h 17m
1 stop
SAN
6:45p
MDW
1:56a
7h 11m
1 stop
Depart: Sat Jun 20 2015 Return: Tue Aug 4 2015 Trip spans 46 days
Delta
Delta
MDW
2:35a
SAN
9:10a
6h 35m
1 stop
SAN
12:39p
MDW
5:59p
5h 20m
1 stop
Depart: Mon Jun 22 2015 Return: Tue Aug 4 2015 Trip spans 44 days
Delta
Delta
MDW
5:08a
SAN
11:25a
6h 17m
1 stop
SAN
12:39p
MDW
5:59p
5h 20m
1 stop
Depart: Thu Jun 25 2015 Return: Mon Jun 29 2015 Trip spans 5 days
Delta
Delta
MDW
5:08a
SAN
11:25a
6h 17m
1 stop
SAN
6:45p
MDW
2:49a
8h 04m
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
243 8:40 am 11:05 am May 25 - May 25
243 8:40 am 11:05 am May 24 - May 24
779 8:40 am 11:05 am Apr 8 - May 22
779 8:40 am 11:05 am Apr 11 - Jun 6
779 8:40 am 11:05 am May 26 - Jun 5
3492 12:20 pm 2:35 pm May 25 - May 25
2061 12:25 pm 2:40 pm May 24 - May 24
2168 12:25 pm 2:40 pm Jun 1 - Jun 5
2168 12:25 pm 2:40 pm May 31 - May 31
2168 12:25 pm 2:40 pm May 26 - May 29
2168 12:25 pm 2:40 pm Apr 8 - May 22
2168 12:25 pm 2:40 pm Apr 12 - May 17
968 2:15 pm 4:30 pm May 23 - May 23
973 2:40 pm 4:55 pm Apr 11 - May 16
973 2:40 pm 4:55 pm May 30 - May 30
3710 3:20 pm 5:35 pm May 25 - May 25
2875 3:30 pm 5:45 pm May 26 - Jun 5
2875 3:30 pm 5:45 pm Apr 8 - May 22
367 3:35 pm 5:50 pm May 24 - May 24
1797 6:40 pm 8:55 pm May 30 - May 30
1797 6:40 pm 8:55 pm Apr 11 - May 16
1829 6:40 pm 8:55 pm May 23 - May 23
4724 7:30 pm 9:50 pm Apr 8 - Jun 5
Airports
Origin

Chicago
$352
Destination

San Diego
$352