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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 Jun 18 2015 Return: Mon Jun 29 2015 Trip spans 12 days
Delta
Delta
MDW
2:35a
SAN
11:25a
8h 50m
1 stop
SAN
6:45p
MDW
2:49a
8h 04m
1 stop
Depart: Sat Jun 20 2015 Return: Mon Jun 29 2015 Trip spans 10 days
Delta
Delta
MDW
8:58a
SAN
5:33p
8h 35m
1 stop
SAN
6:45p
MDW
2:49a
8h 04m
1 stop
Depart: Tue Jun 23 2015 Return: Mon Jun 29 2015 Trip spans 7 days
Delta
Delta
MDW
12:32p
SAN
7:37p
7h 05m
1 stop
SAN
6:45p
MDW
2:49a
8h 04m
1 stop
Depart: Sat Jul 4 2015 Return: Tue Jul 7 2015 Trip spans 4 days
Delta
Delta
MDW
8:58a
SAN
3:10p
6h 12m
1 stop
SAN
12:42p
MDW
5:59p
5h 17m
1 stop
Depart: Fri Jul 10 2015 Return: Tue Jul 14 2015 Trip spans 5 days
Delta
Delta
MDW
3:31p
SAN
9:41p
6h 10m
1 stop
SAN
12:42p
MDW
5:59p
5h 17m
1 stop
Depart: Tue Jul 28 2015 Return: Tue Aug 4 2015 Trip spans 8 days
Delta
Delta
MDW
2:43a
SAN
10:10a
7h 27m
1 stop
SAN
12:42p
MDW
5:59p
5h 17m
1 stop
Depart: Wed Jul 29 2015 Return: Tue Aug 4 2015 Trip spans 7 days
Delta
Delta
MDW
2:43a
SAN
10:10a
7h 27m
1 stop
SAN
12:42p
MDW
5:59p
5h 17m
1 stop
Depart: Thu Aug 13 2015 Return: Tue Aug 18 2015 Trip spans 6 days
Delta
Delta
MDW
3:05a
SAN
10:55a
7h 50m
1 stop
SAN
12:40p
MDW
6:03p
5h 23m
1 stop
Depart: Mon Aug 17 2015 Return: Tue Aug 18 2015 Trip spans 2 days
Delta
Delta
MDW
3:31p
SAN
9:41p
6h 10m
1 stop
SAN
12:40p
MDW
6:03p
5h 23m
1 stop
Depart: Wed Aug 19 2015 Return: Tue Aug 25 2015 Trip spans 7 days
Delta
Delta
MDW
5:55a
SAN
2:52p
8h 57m
1 stop
SAN
4:30a
MDW
10:44a
6h 14m
1 stop
Depart: Thu Aug 20 2015 Return: Mon Aug 24 2015 Trip spans 5 days
Delta
Delta
MDW
3:10a
SAN
11:01a
7h 51m
1 stop
SAN
6:35a
MDW
4:12p
9h 37m
1 stop
Depart: Fri Aug 21 2015 Return: Sat Aug 29 2015 Trip spans 9 days
Delta
Delta
MDW
5:06a
SAN
11:20a
6h 14m
1 stop
SAN
12:00p
MDW
6:03p
6h 03m
1 stop
Depart: Mon Aug 24 2015 Return: Tue Aug 25 2015 Trip spans 2 days
Delta
Delta
MDW
12:33p
SAN
7:41p
7h 08m
1 stop
SAN
6:35a
MDW
2:18p
7h 43m
1 stop
Depart: Wed Aug 26 2015 Return: Sun Aug 30 2015 Trip spans 5 days
Delta
Delta
MDW
2:30a
SAN
9:09a
6h 39m
1 stop
SAN
3:45a
MDW
12:57p
9h 12m
1 stop
Depart: Fri Aug 28 2015 Return: Sun Aug 30 2015 Trip spans 3 days
Delta
Delta
MDW
8:19a
SAN
5:34p
9h 15m
1 stop
SAN
3:45a
MDW
12:57p
9h 12m
1 stop
Depart: Tue Sep 1 2015 Return: Tue Sep 15 2015 Trip spans 15 days
Delta
Delta
MDW
2:00a
SAN
10:44a
8h 44m
1 stop
SAN
12:30p
MDW
5:56p
5h 26m
1 stop
Depart: Wed Sep 2 2015 Return: Sat Sep 5 2015 Trip spans 4 days
Delta
Delta
MDW
5:05a
SAN
11:07a
6h 02m
1 stop
SAN
6:45p
MDW
3:04a
8h 19m
1 stop
Depart: Thu Sep 3 2015 Return: Sun Sep 6 2015 Trip spans 4 days
Delta
Delta
MDW
8:55a
SAN
5:05p
8h 10m
1 stop
SAN
3:10a
MDW
10:10a
7h 00m
1 stop
Depart: Fri Sep 4 2015 Return: Tue Sep 8 2015 Trip spans 5 days
Delta
Delta
MDW
5:05a
SAN
11:07a
6h 02m
1 stop
SAN
3:10a
MDW
10:10a
7h 00m
1 stop
Depart: Tue Jun 2 2015 Return: Mon Jun 8 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
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
295 8:10 am 10:20 am Jun 8 - Aug 7
4181 8:10 am 10:20 am Jun 7 - Aug 2
1396 8:35 am 10:50 am Jun 13 - Jun 27
779 8:40 am 11:05 am May 31 - Jun 5
779 8:40 am 11:05 am May 23 - Jun 6
1196 11:30 am 1:40 pm Jul 3 - Jul 3
698 11:30 am 1:40 pm Jun 8 - Jul 2
698 11:30 am 1:40 pm Jun 7 - Aug 2
2168 12:25 pm 2:40 pm Jun 1 - Jun 5
4527 12:45 pm 2:55 pm Jun 13 - Jun 27
4566 2:35 pm 4:45 pm Jun 7 - Aug 7
973 2:40 pm 4:55 pm Jun 6 - Jun 6
2875 3:30 pm 5:45 pm May 31 - Jun 5
2575 5:30 pm 7:40 pm Jun 13 - Jun 27
1797 6:40 pm 8:55 pm Jun 6 - Jun 6
1089 6:55 pm 9:05 pm Jun 13 - Jun 27
4724 7:30 pm 9:50 pm May 21 - Jun 5
938 8:10 pm 10:20 pm Jul 3 - Jul 3
1802 8:45 pm 10:55 pm Jun 7 - Jul 2
Airports
Origin

Chicago
$390
Destination

San Diego
$390