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Find Deals on Flights 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 Sep 8 2015 Return: Sun Sep 13 2015 Trip spans 6 days
Sun Country Air
Sun Country Air
MDW
4:00a
SAN
10:07a
6h 07m
1 stop
SAN
9:00a
MDW
2:45p
5h 45m
1 stop
Depart: Thu Sep 10 2015 Return: Mon Sep 14 2015 Trip spans 5 days
Sun Country Air
Sun Country Air
MDW
4:00a
SAN
10:07a
6h 07m
1 stop
SAN
9:00a
MDW
2:45p
5h 45m
1 stop
Depart: Fri Sep 11 2015 Return: Mon Sep 14 2015 Trip spans 4 days
Sun Country Air
Sun Country Air
MDW
4:00a
SAN
10:07a
6h 07m
1 stop
SAN
9:00a
MDW
2:45p
5h 45m
1 stop
Depart: Thu Sep 17 2015 Return: Mon Sep 21 2015 Trip spans 5 days
Sun Country Air
Sun Country Air
MDW
4:00a
SAN
10:07a
6h 07m
1 stop
SAN
9:00a
MDW
2:45p
5h 45m
1 stop
Depart: Fri Sep 18 2015 Return: Mon Sep 21 2015 Trip spans 4 days
Sun Country Air
Sun Country Air
MDW
4:00a
SAN
10:07a
6h 07m
1 stop
SAN
9:00a
MDW
2:45p
5h 45m
1 stop
Depart: Mon Sep 21 2015 Return: Thu Sep 24 2015 Trip spans 4 days
Sun Country Air
Sun Country Air
MDW
4:00a
SAN
10:07a
6h 07m
1 stop
SAN
9:00a
MDW
2:45p
5h 45m
1 stop
Depart: Thu Sep 24 2015 Return: Fri Sep 25 2015 Trip spans 2 days
Sun Country Air
Sun Country Air
MDW
4:00a
SAN
10:07a
6h 07m
1 stop
SAN
9:00a
MDW
2:45p
5h 45m
1 stop
Depart: Wed Aug 19 2015 Return: Sun Aug 23 2015 Trip spans 5 days
Delta
Delta
MDW
2:30a
SAN
9:09a
6h 39m
1 stop
SAN
6:45p
MDW
1:56a
7h 11m
1 stop
Depart: Thu Aug 20 2015 Return: Sun Aug 23 2015 Trip spans 4 days
Delta
Delta
MDW
8:58a
SAN
5:29p
8h 31m
1 stop
SAN
6:45p
MDW
1:56a
7h 11m
1 stop
Depart: Fri Aug 21 2015 Return: Sun Aug 23 2015 Trip spans 3 days
Delta
Delta
MDW
11:20a
SAN
5:29p
6h 09m
1 stop
SAN
6:45p
MDW
1:56a
7h 11m
1 stop
Depart: Sat Aug 22 2015 Return: Mon Aug 24 2015 Trip spans 3 days
Delta
Delta
MDW
11:28a
SAN
9:19p
9h 51m
1 stop
SAN
6:35a
MDW
2:18p
7h 43m
1 stop
Depart: Sun Aug 23 2015 Return: Tue Aug 25 2015 Trip spans 3 days
Delta
Delta
MDW
2:40a
SAN
10:11a
7h 31m
1 stop
SAN
5:00a
MDW
2:18p
9h 18m
1 stop
Depart: Tue Aug 25 2015 Return: Sat Aug 29 2015 Trip spans 5 days
Delta
Delta
MDW
11:20a
SAN
5:29p
6h 09m
1 stop
SAN
12:00p
MDW
6:03p
6h 03m
1 stop
Depart: Wed Aug 26 2015 Return: Fri Aug 28 2015 Trip spans 3 days
Delta
Delta
MDW
9:40a
SAN
5:34p
7h 54m
1 stop
SAN
6:35a
MDW
2:18p
7h 43m
1 stop
Depart: Thu Aug 27 2015 Return: Sun Aug 30 2015 Trip spans 4 days
Delta
Delta
MDW
8:31a
SAN
3:27p
6h 56m
1 stop
SAN
6:45p
MDW
1:56a
7h 11m
1 stop
Depart: Fri Aug 28 2015 Return: Sun Aug 30 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
SAN
11:01a
9h 01m
1 stop
SAN
6:45p
MDW
1:56a
7h 11m
1 stop
Depart: Sat Aug 29 2015 Return: Mon Aug 31 2015 Trip spans 3 days
Delta
Delta
MDW
2:40a
SAN
10:13a
7h 33m
1 stop
SAN
6:45p
MDW
2:42a
7h 57m
1 stop
Depart: Sun Aug 30 2015 Return: Mon Aug 31 2015 Trip spans 2 days
Delta
Delta
MDW
2:40a
SAN
10:11a
7h 31m
1 stop
SAN
6:35a
MDW
4:12p
9h 37m
1 stop
Depart: Mon Aug 31 2015 Return: Sat Sep 5 2015 Trip spans 6 days
Delta
Delta
MDW
5:06a
SAN
11:20a
6h 14m
1 stop
SAN
6:30p
MDW
3:12a
8h 42m
1 stop
Depart: Tue Sep 1 2015 Return: Tue Sep 8 2015 Trip spans 8 days
Delta
Delta
MDW
2:35a
SAN
9:06a
6h 31m
1 stop
SAN
3:00a
MDW
9:59a
6h 59m
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 29 - Aug 7
4181 8:10 am 10:20 am Jun 28 - Aug 2
1543 8:25 am 10:50 am Aug 9 - Sep 4
1396 8:35 am 10:50 am Jul 11 - Aug 8
3057 11:25 am 1:40 pm Aug 9 - Sep 4
698 11:30 am 1:40 pm Jul 10 - Aug 7
698 11:30 am 1:40 pm Jun 28 - Aug 2
4527 12:45 pm 2:55 pm Jul 18 - Aug 1
4527 12:45 pm 2:55 pm Aug 8 - Aug 8
4566 2:35 pm 4:45 pm Jun 28 - Aug 7
288 3:10 pm 5:25 pm Aug 9 - Sep 4
2575 5:30 pm 7:40 pm Jul 11 - Aug 1
2575 5:30 pm 7:40 pm Aug 8 - Aug 8
1089 6:55 pm 9:05 pm Jul 11 - Aug 1
44 6:55 pm 9:05 pm Aug 8 - Aug 8
1676 7:45 pm 10:05 pm Aug 9 - Sep 4
1802 8:45 pm 10:55 pm Jul 10 - Aug 7
Airports
Origin

Chicago
$254
Destination

San Diego
$254