Find Deals on Flights from Chicago Midway to San Diego (MDW - SAN)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Chicago Midway to San Diego

(Round-trip)
Depart: Mon Feb 27 2017 Return: Sat Mar 4 2017 Trip spans 6 days
Delta
Delta
MDW
7:25a
SAN
5:58p
10h 33m
1 stop
SAN
1:35a
MDW
8:51a
7h 16m
1 stop
Depart: Fri May 19 2017 Return: Wed May 24 2017 Trip spans 6 days
Major Airline
Major Airline
MDW
2:00a
SAN
7:26a
5h 26m
nonstop
SAN
2:00a
MDW
3:26a
1h 26m
nonstop
Depart: Tue Feb 28 2017 Return: Wed Mar 1 2017 Trip spans 2 days
Delta
Delta
MDW
1:20a
SAN
8:10a
6h 50m
1 stop
SAN
5:50p
MDW
1:39a
7h 49m
1 stop
Depart: Wed Mar 1 2017 Return: Fri Mar 3 2017 Trip spans 3 days
Delta
Delta
MDW
10:40a
SAN
8:15p
9h 35m
1 stop
SAN
5:50p
MDW
2:30a
8h 40m
1 stop
Depart: Fri Mar 3 2017 Return: Sat Mar 4 2017 Trip spans 2 days
Delta
Delta
MDW
8:08a
SAN
5:07p
8h 59m
1 stop
SAN
1:35a
MDW
8:51a
7h 16m
1 stop
Depart: Mon Mar 6 2017 Return: Tue Mar 7 2017 Trip spans 2 days
Delta
Delta
MDW
11:41a
SAN
7:15p
7h 34m
1 stop
SAN
9:15a
MDW
3:00p
5h 45m
1 stop
Depart: Tue Mar 7 2017 Return: Wed Mar 8 2017 Trip spans 2 days
Delta
Delta
MDW
2:10a
SAN
9:57a
7h 47m
1 stop
SAN
5:50p
MDW
1:47a
7h 57m
1 stop
Depart: Wed Mar 8 2017 Return: Tue Mar 14 2017 Trip spans 6 days
Delta
Delta
MDW
7:25a
SAN
5:58p
10h 33m
1 stop
SAN
3:00a
MDW
9:54a
6h 54m
1 stop
Depart: Wed Mar 15 2017 Return: Tue Mar 21 2017 Trip spans 7 days
Delta
Delta
MDW
3:51p
SAN
10:03p
6h 12m
1 stop
SAN
2:30a
MDW
10:57a
8h 27m
1 stop
Depart: Mon Mar 20 2017 Return: Tue Mar 21 2017 Trip spans 2 days
Delta
Delta
MDW
12:35p
SAN
8:25p
7h 50m
1 stop
SAN
2:30a
MDW
10:57a
8h 27m
1 stop
Depart: Tue Mar 21 2017 Return: Tue Mar 28 2017 Trip spans 8 days
Delta
Delta
MDW
8:11a
SAN
5:56p
9h 45m
1 stop
SAN
2:30a
MDW
10:57a
8h 27m
1 stop
Depart: Tue Mar 28 2017 Return: Tue Apr 4 2017 Trip spans 8 days
Delta
Delta
MDW
3:51p
SAN
10:03p
6h 12m
1 stop
SAN
6:30p
MDW
3:37a
9h 07m
1 stop
Depart: Mon Apr 3 2017 Return: Tue Apr 4 2017 Trip spans 2 days
Delta
Delta
MDW
1:27p
SAN
9:51p
8h 24m
1 stop
SAN
6:30p
MDW
3:37a
9h 07m
1 stop
Depart: Wed Apr 5 2017 Return: Tue Apr 11 2017 Trip spans 7 days
Delta
Delta
MDW
1:27p
SAN
9:51p
8h 24m
1 stop
SAN
6:30p
MDW
3:37a
9h 07m
1 stop
Depart: Tue Apr 11 2017 Return: Tue Apr 18 2017 Trip spans 8 days
Delta
Delta
MDW
8:59a
SAN
6:04p
9h 05m
1 stop
SAN
6:30p
MDW
3:37a
9h 07m
1 stop
Depart: Tue Apr 18 2017 Return: Sat Apr 22 2017 Trip spans 5 days
Delta
Delta
MDW
8:59a
SAN
6:04p
9h 05m
1 stop
SAN
2:30a
MDW
8:33a
6h 03m
1 stop
Depart: Wed Apr 19 2017 Return: Sat Apr 22 2017 Trip spans 4 days
Delta
Delta
MDW
1:27p
SAN
9:51p
8h 24m
1 stop
SAN
2:30a
MDW
8:33a
6h 03m
1 stop
Depart: Sat Apr 22 2017 Return: Wed May 3 2017 Trip spans 12 days
Delta
Delta
MDW
11:10a
SAN
6:02p
6h 52m
1 stop
SAN
2:15a
MDW
10:49a
8h 34m
1 stop
Depart: Tue Apr 25 2017 Return: Sat Apr 29 2017 Trip spans 5 days
Delta
Delta
MDW
8:59a
SAN
6:04p
9h 05m
1 stop
SAN
2:30a
MDW
10:51a
8h 21m
1 stop
Depart: Wed Apr 26 2017 Return: Sat Apr 29 2017 Trip spans 4 days
Delta
Delta
MDW
11:52a
SAN
9:03p
9h 11m
1 stop
SAN
2:30a
MDW
10:51a
8h 21m
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
4708 8:25 am 10:45 am Mar 9 - Mar 9
4708 8:25 am 10:45 am Mar 13 - Apr 24
4708 8:25 am 10:45 am Mar 10 - Mar 10
1125 8:35 am 10:55 am Feb 16 - Mar 8
152 8:50 am 11:10 am Mar 18 - Apr 22
152 8:50 am 11:10 am Mar 11 - Mar 11
5211 9:00 am 11:20 am Mar 12 - Apr 23
2370 9:25 am 11:50 am Feb 18 - Mar 4
3695 9:45 am 12:05 pm Feb 19 - Mar 5
2026 11:50 am 2:05 pm Mar 12 - Apr 23
3238 12:50 pm 3:10 pm Feb 19 - Mar 5
2081 1:00 pm 3:20 pm Feb 18 - Mar 4
4805 1:00 pm 3:15 pm Mar 13 - Apr 24
4805 1:00 pm 3:15 pm Mar 9 - Mar 10
2724 1:05 pm 3:20 pm Mar 11 - Mar 11
2724 1:05 pm 3:20 pm Mar 18 - Apr 22
1545 3:05 pm 5:25 pm Feb 16 - Mar 8
3562 4:25 pm 6:40 pm Mar 12 - Apr 23
2202 4:40 pm 6:55 pm Mar 11 - Mar 11
2202 4:40 pm 6:55 pm Mar 18 - Apr 15
1062 5:00 pm 7:15 pm Mar 9 - Mar 10
1062 5:00 pm 7:15 pm Mar 13 - Apr 24
5639 6:35 pm 8:55 pm Feb 18 - Mar 4
1319 6:55 pm 9:10 pm Mar 18 - Apr 22
1319 6:55 pm 9:10 pm Mar 11 - Mar 11
561 7:20 pm 9:35 pm Mar 13 - Apr 24
561 7:20 pm 9:35 pm Mar 9 - Mar 10
1098 7:40 pm 10:05 pm Feb 16 - Mar 8
4585 8:00 pm 10:20 pm Mar 12 - Apr 23
2888 8:10 pm 10:35 pm Feb 19 - Mar 5
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

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Airports
Origin

Chicago
$264
Destination

San Diego
$264
Airlines