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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: Mon May 4 2015 Return: Sun May 10 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: Tue May 5 2015 Return: Tue May 12 2015 Trip spans 8 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: Thu May 7 2015 Return: Sun May 10 2015 Trip spans 4 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: Fri May 8 2015 Return: Sun May 10 2015 Trip spans 3 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: Fri May 1 2015 Return: Mon May 4 2015 Trip spans 4 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: Wed May 6 2015 Return: Wed May 13 2015 Trip spans 8 days
Delta
Delta
MDW
7:02a
SAN
3:40p
8h 38m
2 stops
SAN
6:17a
MDW
3:43p
9h 26m
2 stops
Depart: Sun May 10 2015 Return: Wed May 20 2015 Trip spans 11 days
Delta
Delta
MDW
2:00p
SAN
9:29p
7h 29m
1 stop
SAN
6:17a
MDW
3:02p
8h 45m
2 stops
Depart: Mon Apr 13 2015 Return: Thu Apr 23 2015 Trip spans 11 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: Fri Apr 17 2015 Return: Fri May 1 2015 Trip spans 15 days
Sun Country Air
Sun Country Air
MDW
6:30a
SAN
2:35p
8h 05m
1 stop
SAN
9:00a
MDW
2:45p
5h 45m
1 stop
Depart: Fri Apr 24 2015 Return: Fri May 1 2015 Trip spans 8 days
Sun Country Air
Sun Country Air
MDW
6:30a
SAN
2:35p
8h 05m
1 stop
SAN
9:00a
MDW
2:45p
5h 45m
1 stop
Depart: Sat Apr 18 2015 Return: Sun Apr 19 2015 Trip spans 2 days
Delta
Delta
MDW
11:07a
SAN
5:31p
6h 24m
1 stop
SAN
2:25a
MDW
8:37a
6h 12m
1 stop
Depart: Mon Apr 20 2015 Return: Tue Apr 21 2015 Trip spans 2 days
Delta
Delta
MDW
5:08a
SAN
11:06a
5h 58m
1 stop
SAN
2:25a
MDW
8:37a
6h 12m
1 stop
Depart: Tue Apr 21 2015 Return: Thu Apr 23 2015 Trip spans 3 days
Delta
Delta
MDW
5:08a
SAN
11:02a
5h 54m
1 stop
SAN
2:25a
MDW
8:37a
6h 12m
1 stop
Depart: Wed Apr 22 2015 Return: Fri Apr 24 2015 Trip spans 3 days
Delta
Delta
MDW
2:25a
SAN
9:21a
6h 56m
1 stop
SAN
6:30p
MDW
3:13a
8h 43m
1 stop
Depart: Sat Apr 25 2015 Return: Tue Apr 28 2015 Trip spans 4 days
Delta
Delta
MDW
1:57p
SAN
9:48p
7h 51m
1 stop
SAN
4:00a
MDW
10:35a
6h 35m
1 stop
Depart: Mon Apr 27 2015 Return: Tue Apr 28 2015 Trip spans 2 days
Delta
Delta
MDW
12:00p
SAN
7:22p
7h 22m
1 stop
SAN
3:00a
MDW
9:55a
6h 55m
1 stop
Depart: Tue Apr 28 2015 Return: Wed Apr 29 2015 Trip spans 2 days
Delta
Delta
MDW
2:25a
SAN
9:21a
6h 56m
1 stop
SAN
2:25a
MDW
8:37a
6h 12m
1 stop
Depart: Wed Apr 29 2015 Return: Fri May 1 2015 Trip spans 3 days
Delta
Delta
MDW
2:25a
SAN
11:06a
8h 41m
1 stop
SAN
6:47a
MDW
1:58p
7h 11m
1 stop
Depart: Thu Apr 30 2015 Return: Sat May 2 2015 Trip spans 3 days
Delta
Delta
MDW
2:25a
SAN
9:21a
6h 56m
1 stop
SAN
6:47a
MDW
4:07p
9h 20m
1 stop
Depart: Sat May 2 2015 Return: Mon May 4 2015 Trip spans 3 days
Delta
Delta
MDW
1:59p
SAN
9:26p
7h 27m
1 stop
SAN
2:25a
MDW
8:42a
6h 17m
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
4004 8:40 am 11:10 am Mar 29 - Apr 5
779 8:40 am 11:05 am Apr 11 - Jun 6
779 8:40 am 11:05 am Apr 8 - May 22
3231 8:45 am 11:15 am Mar 26 - Apr 6
694 8:45 am 11:15 am Apr 7 - Apr 7
4553 11:15 am 1:35 pm Mar 29 - Apr 7
2168 12:25 pm 2:40 pm Apr 12 - May 17
2168 12:25 pm 2:40 pm Apr 8 - May 22
1227 2:20 pm 4:40 pm Apr 7 - Apr 7
328 2:20 pm 4:40 pm Mar 26 - Apr 6
973 2:40 pm 4:55 pm Apr 11 - May 16
2875 3:30 pm 5:45 pm Apr 8 - May 22
1797 6:40 pm 8:55 pm Apr 11 - May 16
151 7:25 pm 9:55 pm Mar 26 - 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
$352
Destination

San Diego
$352