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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: Tue Mar 31 2015 Return: Tue Apr 14 2015 Trip spans 15 days
Delta
Delta
MDW
7:07a
SAN
3:39p
8h 32m
2 stops
SAN
4:15a
MDW
11:21a
7h 06m
1 stop
Depart: Mon Apr 13 2015 Return: Sun Apr 26 2015 Trip spans 14 days
Sun Country Air
Sun Country Air
MDW
6:30a
SAN
2:35p
8h 05m
1 stop
SAN
5:55a
MDW
11:45a
5h 50m
1 stop
Depart: Tue Mar 24 2015 Return: Tue Apr 7 2015 Trip spans 15 days
Delta
Delta
MDW
7:07a
SAN
3:39p
8h 32m
2 stops
SAN
6:30p
MDW
3:15a
8h 45m
1 stop
Depart: Mon Mar 30 2015 Return: Tue Apr 7 2015 Trip spans 9 days
Delta
Delta
MDW
1:14p
SAN
8:51p
7h 37m
2 stops
SAN
6:30p
MDW
3:15a
8h 45m
1 stop
Depart: Fri Apr 17 2015 Return: Tue Apr 21 2015 Trip spans 5 days
Delta
Delta
MDW
8:55a
SAN
8:57p
12h 02m
2 stops
SAN
2:15a
MDW
11:57a
9h 42m
2 stops
Depart: Sat Apr 18 2015 Return: Tue Apr 21 2015 Trip spans 4 days
Delta
Delta
MDW
11:07a
SAN
8:55p
9h 48m
2 stops
SAN
2:15a
MDW
1:54p
11h 39m
2 stops
Depart: Sat Apr 25 2015 Return: Tue Apr 28 2015 Trip spans 4 days
Delta
Delta
MDW
7:00a
SAN
3:38p
8h 38m
2 stops
SAN
2:15a
MDW
9:55a
7h 40m
2 stops
Depart: Tue Apr 28 2015 Return: Fri May 1 2015 Trip spans 4 days
Delta
Delta
MDW
2:25a
SAN
1:49p
11h 24m
2 stops
SAN
2:15a
MDW
12:56p
10h 41m
2 stops
Depart: Sat May 2 2015 Return: Fri May 8 2015 Trip spans 7 days
Delta
Delta
MDW
11:12a
SAN
8:49p
9h 37m
2 stops
SAN
2:15a
MDW
10:39a
8h 24m
2 stops
Depart: Mon May 4 2015 Return: Mon May 11 2015 Trip spans 8 days
Delta
Delta
MDW
7:02a
SAN
3:40p
8h 38m
2 stops
SAN
2:15a
MDW
10:39a
8h 24m
2 stops
Depart: Sat May 9 2015 Return: Mon May 11 2015 Trip spans 3 days
Delta
Delta
MDW
8:35a
SAN
6:50p
10h 15m
2 stops
SAN
2:15a
MDW
10:39a
8h 24m
2 stops
Depart: Sat May 30 2015 Return: Tue Jun 2 2015 Trip spans 4 days
Delta
Delta
MDW
7:02a
SAN
3:38p
8h 36m
2 stops
SAN
2:15a
MDW
10:39a
8h 24m
2 stops
Depart: Wed Apr 15 2015 Return: Wed Apr 22 2015 Trip spans 8 days
Delta
Delta
MDW
5:08a
SAN
11:02a
5h 54m
1 stop
SAN
2:15a
MDW
10:35a
8h 20m
2 stops
Depart: Mon Apr 20 2015 Return: Tue Apr 21 2015 Trip spans 2 days
Delta
Delta
MDW
11:07a
SAN
5:34p
6h 27m
1 stop
SAN
2:15a
MDW
9:55a
7h 40m
2 stops
Depart: Tue Apr 21 2015 Return: Mon Apr 27 2015 Trip spans 7 days
Delta
Delta
MDW
3:00a
SAN
1:49p
10h 49m
2 stops
SAN
6:30p
MDW
3:15a
8h 45m
1 stop
Depart: Wed Apr 22 2015 Return: Mon Apr 27 2015 Trip spans 6 days
Delta
Delta
MDW
7:05a
SAN
3:38p
8h 33m
2 stops
SAN
6:30p
MDW
3:15a
8h 45m
1 stop
Depart: Fri Apr 24 2015 Return: Tue Apr 28 2015 Trip spans 5 days
Delta
Delta
MDW
1:57p
SAN
9:52p
7h 55m
1 stop
SAN
2:15a
MDW
10:35a
8h 20m
2 stops
Depart: Wed Apr 29 2015 Return: Sat May 2 2015 Trip spans 4 days
Delta
Delta
MDW
2:25a
SAN
11:06a
8h 41m
1 stop
SAN
2:15a
MDW
10:38a
8h 23m
2 stops
Depart: Sun May 3 2015 Return: Sat May 9 2015 Trip spans 7 days
Delta
Delta
MDW
2:45a
SAN
10:48a
8h 03m
1 stop
SAN
2:15a
MDW
10:38a
8h 23m
2 stops
Depart: Thu May 7 2015 Return: Mon May 11 2015 Trip spans 5 days
Delta
Delta
MDW
2:45a
SAN
9:15a
6h 30m
1 stop
SAN
2:15a
MDW
10:39a
8h 24m
2 stops
Change your search
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
2730 8:40 am 11:10 am Mar 14 - Apr 4
4004 8:40 am 11:10 am Mar 8 - Apr 5
779 8:40 am 11:05 am Apr 8 - May 22
3231 8:45 am 11:15 am Mar 9 - Apr 6
694 8:45 am 11:15 am Apr 7 - Apr 7
4553 11:15 am 1:35 pm Mar 22 - Mar 27
4553 11:15 am 1:35 pm Mar 24 - Mar 26
4553 11:15 am 1:35 pm Mar 8 - Mar 20
4553 11:15 am 1:35 pm Mar 29 - Apr 7
2168 12:25 pm 2:40 pm Apr 8 - May 22
2426 12:35 pm 3:00 pm Mar 14 - Apr 4
1227 2:20 pm 4:40 pm Apr 7 - Apr 7
328 2:20 pm 4:40 pm Mar 8 - Apr 6
2875 3:30 pm 5:45 pm Apr 8 - May 22
1552 5:40 pm 8:05 pm Mar 14 - Apr 4
179 6:55 pm 9:25 pm Mar 14 - Apr 4
151 7:25 pm 9:55 pm Mar 8 - Apr 6
3833 7:25 pm 9:55 pm Apr 7 - Apr 7
4724 7:30 pm 9:50 pm Apr 8 - Jun 5
Airports
Origin

Chicago
$361
Destination

San Diego
$361