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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: Sat Apr 11 2015 Return: Tue Apr 14 2015 Trip spans 4 days
Delta
Delta
MDW
5:05a
SAN
1:59p
8h 54m
2 stops
SAN
6:15a
MDW
2:53p
8h 38m
2 stops
Depart: Sat Apr 18 2015 Return: Sat Apr 25 2015 Trip spans 8 days
Delta
Delta
MDW
11:10a
SAN
8:30p
9h 20m
2 stops
SAN
2:10a
MDW
10:10a
8h 00m
2 stops
Depart: Wed Apr 22 2015 Return: Tue Apr 28 2015 Trip spans 7 days
Delta
Delta
MDW
2:45a
SAN
10:20a
7h 35m
2 stops
SAN
2:10a
MDW
10:51a
8h 41m
2 stops
Depart: Tue Mar 10 2015 Return: Tue Mar 17 2015 Trip spans 8 days
Delta
Delta
MDW
5:20a
SAN
1:48p
8h 28m
2 stops
SAN
6:19a
MDW
3:47p
9h 28m
2 stops
Depart: Thu Feb 19 2015 Return: Tue Feb 24 2015 Trip spans 6 days
Delta
Delta
MDW
10:19a
SAN
7:33p
9h 14m
1 stop
SAN
5:13a
MDW
2:49p
9h 36m
2 stops
Depart: Fri Feb 20 2015 Return: Wed Feb 25 2015 Trip spans 6 days
Delta
Delta
MDW
11:34a
SAN
7:04p
7h 30m
1 stop
SAN
1:15a
MDW
9:33a
8h 18m
2 stops
Depart: Sat Feb 21 2015 Return: Wed Feb 25 2015 Trip spans 5 days
Delta
Delta
MDW
4:46a
SAN
3:15p
10h 29m
1 stop
SAN
1:15a
MDW
9:33a
8h 18m
2 stops
Depart: Mon Feb 23 2015 Return: Tue Mar 3 2015 Trip spans 9 days
Delta
Delta
MDW
4:08a
SAN
10:53a
6h 45m
1 stop
SAN
1:15a
MDW
9:40a
8h 25m
2 stops
Depart: Tue Feb 24 2015 Return: Tue Mar 3 2015 Trip spans 8 days
Delta
Delta
MDW
10:10a
SAN
4:57p
6h 47m
1 stop
SAN
1:15a
MDW
9:40a
8h 25m
2 stops
Depart: Thu Feb 26 2015 Return: Tue Mar 10 2015 Trip spans 12 days
Delta
Delta
MDW
10:19a
SAN
7:33p
9h 14m
1 stop
SAN
2:15a
MDW
10:40a
8h 25m
2 stops
Depart: Fri Feb 27 2015 Return: Tue Mar 3 2015 Trip spans 5 days
Delta
Delta
MDW
11:34a
SAN
7:04p
7h 30m
1 stop
SAN
5:19a
MDW
2:47p
9h 28m
2 stops
Depart: Sat Feb 28 2015 Return: Tue Mar 3 2015 Trip spans 4 days
Delta
Delta
MDW
1:00a
SAN
9:58a
8h 58m
1 stop
SAN
1:15a
MDW
9:40a
8h 25m
2 stops
Depart: Tue Mar 3 2015 Return: Tue Mar 17 2015 Trip spans 14 days
Delta
Delta
MDW
6:07a
SAN
2:39p
8h 32m
2 stops
SAN
6:50p
MDW
2:45a
7h 55m
1 stop
Depart: Sat Mar 21 2015 Return: Tue Mar 24 2015 Trip spans 4 days
Delta
Delta
MDW
12:34p
SAN
7:53p
7h 19m
1 stop
SAN
2:15a
MDW
10:40a
8h 25m
2 stops
Depart: Thu Mar 12 2015 Return: Tue Mar 17 2015 Trip spans 6 days
Delta
Delta
MDW
10:11a
SAN
7:24p
9h 13m
1 stop
SAN
6:19a
MDW
3:47p
9h 28m
2 stops
Depart: Tue Feb 17 2015 Return: Thu Feb 19 2015 Trip spans 3 days
Delta
Delta
MDW
9:06a
SAN
7:34p
10h 28m
1 stop
SAN
1:15a
MDW
10:58a
9h 43m
2 stops
Depart: Tue Apr 7 2015 Return: Tue Apr 14 2015 Trip spans 8 days
Delta
Delta
MDW
8:10a
SAN
3:42p
7h 32m
2 stops
SAN
6:15a
MDW
2:53p
8h 38m
2 stops
Depart: Tue Apr 21 2015 Return: Sat Apr 25 2015 Trip spans 5 days
Delta
Delta
MDW
11:27a
SAN
9:39p
10h 12m
1 stop
SAN
2:10a
MDW
10:10a
8h 00m
2 stops
Depart: Thu Apr 23 2015 Return: Sat Apr 25 2015 Trip spans 3 days
Delta
Delta
MDW
2:45a
SAN
9:03a
6h 18m
1 stop
SAN
2:10a
MDW
10:10a
8h 00m
2 stops
Depart: Fri Apr 17 2015 Return: Sun Apr 19 2015 Trip spans 3 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
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
4004 8:40 am 11:10 am Mar 8 - Apr 5
483 8:40 am 11:10 am Mar 7 - Mar 7
2514 8:55 am 11:25 am Feb 1 - Mar 1
2514 8:55 am 11:25 am Jan 27 - Mar 6
3379 9:30 am 11:55 am Jan 31 - Feb 28
4553 11:15 am 1:35 pm Mar 8 - Mar 20
351 12:35 pm 3:00 pm Mar 7 - Mar 7
1687 2:00 pm 4:30 pm Feb 8 - Mar 1
2187 2:00 pm 4:30 pm Jan 27 - Mar 6
328 2:20 pm 4:40 pm Mar 8 - Apr 6
1552 5:40 pm 8:05 pm Mar 7 - Mar 7
2480 6:35 pm 9:10 pm Jan 31 - Feb 28
1870 7:15 pm 9:45 pm Mar 7 - Mar 7
2364 7:15 pm 9:50 pm Feb 8 - Mar 6
2364 7:15 pm 9:50 pm Jan 27 - Feb 6
151 7:25 pm 9:55 pm Mar 8 - Apr 6
Airports
Origin

Chicago
$330
Destination

San Diego
$330