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
Students
under 26
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 Dec 12 2016 Return: Wed Dec 14 2016 Trip spans 3 days
Delta
Delta
MDW
10:40a
SAN
8:06p
9h 26m
1 stop
SAN
7:30a
MDW
2:56p
7h 26m
1 stop
Depart: Tue Dec 6 2016 Return: Tue Dec 13 2016 Trip spans 8 days
Major Airline
Major Airline
MDW
12:00a
SAN
5:26a
5h 26m
nonstop
SAN
8:00a
MDW
9:26a
1h 26m
nonstop
Depart: Mon Apr 10 2017 Return: Mon Apr 17 2017 Trip spans 8 days
Southwest
Southwest
MDW
3:20p
SAN
7:35p
4h 15m
nonstop
SAN
2:30p
MDW
6:20p
3h 50m
nonstop
Depart: Fri Dec 16 2016 Return: Mon Jan 9 2017 Trip spans 25 days
Delta
Delta
MDW
1:30a
SAN
10:24a
8h 54m
1 stop
SAN
5:30p
MDW
2:55a
9h 25m
1 stop
Depart: Tue Jan 10 2017 Return: Wed Jan 11 2017 Trip spans 2 days
Delta
Delta
MDW
10:29a
SAN
4:56p
6h 27m
1 stop
SAN
5:30p
MDW
2:55a
9h 25m
1 stop
Depart: Wed Jan 11 2017 Return: Sat Jan 14 2017 Trip spans 4 days
Delta
Delta
MDW
10:40a
SAN
8:18p
9h 38m
1 stop
SAN
3:10a
MDW
10:19a
7h 09m
1 stop
Depart: Sun Jan 15 2017 Return: Sat Jan 21 2017 Trip spans 7 days
Delta
Delta
MDW
10:40a
SAN
8:15p
9h 35m
1 stop
SAN
1:25a
MDW
8:00a
6h 35m
1 stop
Depart: Wed Jan 18 2017 Return: Sat Jan 21 2017 Trip spans 4 days
Delta
Delta
MDW
11:50a
SAN
7:48p
7h 58m
1 stop
SAN
2:15a
MDW
9:09a
6h 54m
1 stop
Depart: Thu Jan 19 2017 Return: Sat Jan 21 2017 Trip spans 3 days
Delta
Delta
MDW
8:09a
SAN
4:56p
8h 47m
1 stop
SAN
1:25a
MDW
8:00a
6h 35m
1 stop
Depart: Fri Jan 20 2017 Return: Sat Jan 21 2017 Trip spans 2 days
Delta
Delta
MDW
1:20a
SAN
8:12a
6h 52m
1 stop
SAN
1:25a
MDW
8:00a
6h 35m
1 stop
Depart: Thu Dec 22 2016 Return: Mon Dec 26 2016 Trip spans 5 days
Major Airline
Major Airline
MDW
1:00a
SAN
6:26a
5h 26m
1 stop
SAN
1:00a
MDW
2:26a
1h 26m
1 stop
Depart: Sat Jan 21 2017 Return: Mon Jan 23 2017 Trip spans 3 days
Delta
Delta
MDW
7:15a
SAN
2:35p
7h 20m
1 stop
SAN
1:25a
MDW
7:54a
6h 29m
1 stop
Depart: Sun Jan 22 2017 Return: Wed Jan 25 2017 Trip spans 4 days
Delta
Delta
MDW
3:30a
SAN
10:37a
7h 07m
1 stop
SAN
6:52a
MDW
2:00p
7h 08m
1 stop
Depart: Mon Jan 23 2017 Return: Wed Jan 25 2017 Trip spans 3 days
Delta
Delta
MDW
4:24a
SAN
10:37a
6h 13m
1 stop
SAN
6:52a
MDW
2:00p
7h 08m
1 stop
Depart: Wed Jan 25 2017 Return: Sun Jan 29 2017 Trip spans 5 days
Delta
Delta
MDW
10:40a
SAN
8:18p
9h 38m
1 stop
SAN
2:15a
MDW
11:05a
8h 50m
1 stop
Depart: Thu Jan 26 2017 Return: Sun Jan 29 2017 Trip spans 4 days
Delta
Delta
MDW
10:40a
SAN
8:18p
9h 38m
1 stop
SAN
2:15a
MDW
11:05a
8h 50m
1 stop
Depart: Fri Jan 27 2017 Return: Sun Jan 29 2017 Trip spans 3 days
Delta
Delta
MDW
11:50a
SAN
7:48p
7h 58m
1 stop
SAN
2:15a
MDW
11:05a
8h 50m
1 stop
Depart: Sat Jan 28 2017 Return: Sun Jan 29 2017 Trip spans 2 days
Delta
Delta
MDW
8:45a
SAN
6:47p
10h 02m
1 stop
SAN
2:15a
MDW
11:05a
8h 50m
1 stop
Depart: Wed Feb 1 2017 Return: Sat Feb 4 2017 Trip spans 4 days
Delta
Delta
MDW
10:40a
SAN
8:18p
9h 38m
1 stop
SAN
1:30a
MDW
10:19a
8h 49m
1 stop
Depart: Thu Feb 2 2017 Return: Sat Feb 4 2017 Trip spans 3 days
Delta
Delta
MDW
7:20a
SAN
5:55p
10h 35m
1 stop
SAN
1:30a
MDW
10:19a
8h 49m
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
1519 8:00 am 10:25 am Dec 21 - Jan 2
2983 8:15 am 10:40 am Dec 4 - Dec 20
2983 8:15 am 10:40 am Jan 1 - Jan 4
3517 8:15 am 10:40 am Dec 25 - Dec 25
1125 8:35 am 10:55 am Jan 5 - Feb 13
1622 9:00 am 11:30 am Dec 17 - Dec 17
1850 9:15 am 11:45 am Dec 24 - Dec 24
2341 9:15 am 11:45 am Dec 31 - Dec 31
2370 9:25 am 11:50 am Jan 7 - Mar 4
3695 9:45 am 12:05 pm Jan 8 - Jan 29
1360 11:45 am 2:15 pm Dec 4 - Dec 18
1360 11:45 am 2:15 pm Jan 1 - Jan 1
1845 11:45 am 2:15 pm Dec 25 - Dec 25
385 11:45 am 2:15 pm Jan 3 - Jan 4
385 11:45 am 2:15 pm Dec 5 - Dec 20
3451 12:05 pm 2:35 pm Dec 17 - Dec 17
3238 12:50 pm 3:10 pm Jan 8 - Jan 29
2081 1:00 pm 3:20 pm Jan 7 - Mar 4
1086 1:45 pm 4:20 pm Dec 24 - Dec 24
5727 1:45 pm 4:20 pm Dec 31 - Dec 31
6035 2:40 pm 5:10 pm Dec 21 - Dec 28
6035 2:40 pm 5:10 pm Dec 29 - Jan 2
1545 3:05 pm 5:25 pm Jan 6 - Jan 13
1545 3:05 pm 5:25 pm Jan 5 - Jan 9
1338 5:10 pm 7:40 pm Dec 17 - Dec 17
6849 6:30 pm 9:00 pm Dec 31 - Dec 31
5639 6:35 pm 8:55 pm Jan 7 - Mar 4
3944 7:20 pm 9:50 pm Dec 25 - Dec 25
871 7:20 pm 9:50 pm Jan 1 - Jan 4
871 7:20 pm 9:50 pm Dec 4 - Dec 20
982 7:25 pm 9:55 pm Dec 24 - Dec 24
1098 7:40 pm 10:05 pm Jan 5 - Mar 8
1341 7:40 pm 10:15 pm Dec 17 - Dec 17
2888 8:10 pm 10:35 pm Jan 8 - Jan 29
4627 8:15 pm 10:50 pm Dec 21 - Jan 2
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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 Airline reviews

6 travelers who booked a flight from Chicago to San Diego rated their chosen airlines with an average of 9.4.

Overall
9.7
Boarding
10.0
Crew
9.7
Comfort
9.7
Food
8.7
Entertainment
8.7