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

Depart
Return
1 adult
Cabin Economy
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
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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: Fri Dec 9 2016 Return: Tue Dec 13 2016 Trip spans 5 days
$144
Select
Major Airline
Major Airline
MDW
2:20p
→
SAN
6:50p
4h 30m
nonstop
SAN
1:20a
→
MDW
5:30a
4h 10m
nonstop
Depart: Sat Oct 8 2016 Return: Tue Oct 11 2016 Trip spans 4 days
$264
Select
Delta
Delta
MDW
11:20a
→
SAN
5:29p
6h 09m
1 stop
SAN
2:30a
→
MDW
10:49a
8h 19m
1 stop
Show reviews
7.8 Good (5305 reviews)
Depart: Tue Jan 3 2017 Return: Mon Jan 9 2017 Trip spans 7 days
$378
Select
Southwest
Southwest
MDW
2:20p
→
SAN
8:30p
6h 10m
1 stop
SAN
9:50a
→
MDW
1:45p
3h 55m
nonstop
Show reviews
8.3 Excellent (1714 reviews)
Depart: Tue Oct 25 2016 Return: Wed Nov 2 2016 Trip spans 9 days
$200
Select
Major Airline
Major Airline
MDW
6:30a
→
SAN
10:40a
4h 10m
nonstop
SAN
1:50p
→
MDW
5:45p
3h 55m
nonstop
Depart: Wed Nov 2 2016 Return: Mon Nov 7 2016 Trip spans 6 days
$200
Select
Major Airline
Major Airline
MDW
11:10a
→
SAN
3:20p
4h 10m
nonstop
SAN
10:05a
→
MDW
1:55p
3h 50m
nonstop
Depart: Sun Nov 6 2016 Return: Mon Nov 7 2016 Trip spans 2 days
$200
Select
Major Airline
Major Airline
MDW
3:15a
→
SAN
7:40a
4h 25m
nonstop
SAN
10:05a
→
MDW
1:55p
3h 50m
nonstop
Depart: Wed Oct 12 2016 Return: Sat Oct 15 2016 Trip spans 4 days
$264
Select
Delta
Delta
MDW
2:00a
→
SAN
9:41a
7h 41m
1 stop
SAN
2:30a
→
MDW
8:45a
6h 15m
1 stop
Show reviews
7.8 Good (5305 reviews)
Depart: Tue Nov 8 2016 Return: Sat Nov 12 2016 Trip spans 5 days
$200
Select
Major Airline
Major Airline
MDW
6:45a
→
SAN
11:15a
4h 30m
nonstop
SAN
1:45a
→
MDW
5:45a
4h 00m
nonstop
Depart: Sat Oct 22 2016 Return: Sat Oct 29 2016 Trip spans 8 days
$264
Select
Delta
Delta
MDW
2:30a
→
SAN
11:12a
8h 42m
1 stop
SAN
8:36a
→
MDW
4:52p
8h 16m
1 stop
Show reviews
7.8 Good (5305 reviews)
Depart: Sun Dec 4 2016 Return: Thu Dec 8 2016 Trip spans 5 days
$200
Select
Major Airline
Major Airline
MDW
6:45a
→
SAN
11:15a
4h 30m
nonstop
SAN
10:05a
→
MDW
1:55p
3h 50m
nonstop
Depart: Wed Oct 26 2016 Return: Sat Oct 29 2016 Trip spans 4 days
$264
Select
Delta
Delta
MDW
9:01a
→
SAN
5:33p
8h 32m
1 stop
SAN
2:30a
→
MDW
10:48a
8h 18m
1 stop
Show reviews
7.8 Good (5305 reviews)
Depart: Sat Dec 10 2016 Return: Wed Dec 14 2016 Trip spans 5 days
$211
Select
Major Airline
Major Airline
MDW
4:15a
→
SAN
8:45a
4h 30m
nonstop
SAN
10:05a
→
MDW
1:55p
3h 50m
nonstop
Depart: Fri Oct 28 2016 Return: Mon Oct 31 2016 Trip spans 4 days
$264
Select
Delta
Delta
MDW
9:01a
→
SAN
5:33p
8h 32m
1 stop
SAN
3:00a
→
MDW
9:58a
6h 58m
1 stop
Depart: Sat Nov 5 2016 Return: Tue Nov 8 2016 Trip spans 4 days
$264
Select
Delta
Delta
MDW
12:40p
→
SAN
7:52p
7h 12m
1 stop
SAN
8:56a
→
MDW
3:57p
7h 01m
1 stop
Depart: Mon Dec 12 2016 Return: Thu Dec 15 2016 Trip spans 4 days
$222
Select
Major Airline
Major Airline
MDW
3:15a
→
SAN
7:40a
4h 25m
nonstop
SAN
8:55a
→
MDW
12:45p
3h 50m
nonstop
Depart: Wed Nov 9 2016 Return: Thu Nov 10 2016 Trip spans 2 days
$264
Select
Delta
Delta
MDW
10:40a
→
SAN
8:13p
9h 33m
1 stop
SAN
7:30a
→
MDW
2:56p
7h 26m
1 stop
Depart: Mon Nov 14 2016 Return: Tue Nov 15 2016 Trip spans 2 days
$264
Select
Delta
Delta
MDW
8:03a
→
SAN
5:04p
9h 01m
1 stop
SAN
1:28a
→
MDW
7:55a
6h 27m
1 stop
Depart: Wed Oct 19 2016 Return: Tue Nov 8 2016 Trip spans 21 days
$251
Select
Major Airline
Major Airline
MDW
2:55p
→
SAN
7:10p
4h 15m
nonstop
SAN
10:05a
→
MDW
1:55p
3h 50m
nonstop
Depart: Mon Nov 21 2016 Return: Wed Nov 30 2016 Trip spans 10 days
$264
Select
Delta
Delta
MDW
10:27a
→
SAN
5:04p
6h 37m
1 stop
SAN
1:25a
→
MDW
7:37a
6h 12m
1 stop
Depart: Thu Dec 1 2016 Return: Tue Dec 6 2016 Trip spans 6 days
$251
Select
Major Airline
Major Airline
MDW
2:20p
→
SAN
6:50p
4h 30m
nonstop
SAN
10:05a
→
MDW
1:55p
3h 50m
nonstop
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
2983 8:15 am 10:40 am ✈ ✈ ✈ ✈ ✈ Nov 6 - Nov 14
1255 8:30 am 10:45 am ✈ Oct 31 - Oct 31
3172 8:30 am 10:45 am ✈ ✈ ✈ ✈ ✈ Oct 3 - Oct 28
3172 8:30 am 10:45 am ✈ ✈ ✈ ✈ Nov 1 - Nov 4
3389 8:30 am 10:45 am ✈ Oct 2 - Oct 30
3272 8:55 am 11:10 am ✈ Oct 8 - Nov 5
1110 10:30 am 12:40 pm ✈ Oct 31 - Oct 31
1110 10:30 am 12:40 pm ✈ ✈ ✈ ✈ Nov 1 - Nov 4
1110 10:30 am 12:40 pm ✈ ✈ ✈ ✈ ✈ ✈ Oct 2 - Oct 30
2536 11:40 am 1:50 pm ✈ Oct 8 - Nov 5
1360 11:45 am 2:15 pm ✈ Nov 6 - Nov 20
1908 3:10 pm 5:20 pm ✈ ✈ ✈ ✈ ✈ ✈ Sep 27 - Oct 30
1908 3:10 pm 5:20 pm ✈ ✈ ✈ ✈ Nov 1 - Nov 4
132 3:15 pm 5:25 pm ✈ Oct 31 - Oct 31
3606 3:45 pm 6:00 pm ✈ Oct 8 - Oct 29
3606 4:40 pm 6:55 pm ✈ Nov 5 - Nov 5
150 6:50 pm 9:05 pm ✈ Nov 5 - Nov 5
327 6:50 pm 9:05 pm ✈ Oct 8 - Oct 29
3069 6:55 pm 9:10 pm ✈ ✈ ✈ ✈ ✈ ✈ Oct 2 - Oct 30
3069 6:55 pm 9:10 pm ✈ ✈ ✈ ✈ Nov 1 - Nov 4
871 7:20 pm 9:50 pm ✈ ✈ ✈ ✈ ✈ Nov 6 - Nov 14
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin
Chicago
$144
Destination
San Diego
$144
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