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

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 San Diego to Chicago Midway

(Round-trip)
Depart: Sat Feb 11 2017 Return: Sun Feb 12 2017 Trip spans 2 days
Southwest
Southwest
SAN
1:40a
MDW
5:45a
4h 05m
nonstop
MDW
4:45a
SAN
9:05a
4h 20m
nonstop
Depart: Tue Dec 13 2016 Return: Fri Jan 6 2017 Trip spans 25 days
Delta
Delta
SAN
1:25a
MDW
10:00a
8h 35m
1 stop
MDW
10:16a
SAN
5:04p
6h 48m
1 stop
Depart: Fri Dec 9 2016 Return: Mon Dec 12 2016 Trip spans 4 days
Major Airline
Major Airline
SAN
12:00a
MDW
1:26a
1h 26m
nonstop
MDW
8:00a
SAN
1:26p
5h 26m
nonstop
Depart: Wed Dec 14 2016 Return: Thu Dec 15 2016 Trip spans 2 days
Delta
Delta
SAN
8:56a
MDW
3:36p
6h 40m
1 stop
MDW
1:30a
SAN
10:24a
8h 54m
1 stop
Depart: Thu Dec 15 2016 Return: Fri Jan 6 2017 Trip spans 23 days
Delta
Delta
SAN
2:15a
MDW
9:01a
6h 46m
1 stop
MDW
10:28a
SAN
7:11p
8h 43m
1 stop
Depart: Fri Dec 16 2016 Return: Fri Jan 6 2017 Trip spans 22 days
Delta
Delta
SAN
2:15a
MDW
10:59a
8h 44m
1 stop
MDW
10:16a
SAN
5:04p
6h 48m
1 stop
Depart: Sun Dec 18 2016 Return: Fri Jan 6 2017 Trip spans 20 days
Delta
Delta
SAN
7:47a
MDW
3:21p
7h 34m
1 stop
MDW
10:28a
SAN
7:11p
8h 43m
1 stop
Depart: Sun Dec 25 2016 Return: Mon Jan 9 2017 Trip spans 16 days
Delta
Delta
SAN
1:25a
MDW
7:50a
6h 25m
1 stop
MDW
10:33a
SAN
4:56p
6h 23m
1 stop
Depart: Tue Feb 21 2017 Return: Sun Feb 26 2017 Trip spans 6 days
Southwest
Southwest
SAN
1:20a
MDW
5:25a
4h 05m
nonstop
MDW
4:45a
SAN
9:05a
4h 20m
nonstop
Depart: Fri Jan 6 2017 Return: Sun Jan 8 2017 Trip spans 3 days
Delta
Delta
SAN
7:55a
MDW
3:05p
7h 10m
1 stop
MDW
4:00a
SAN
10:37a
6h 37m
1 stop
Depart: Tue Jan 10 2017 Return: Sun Jan 15 2017 Trip spans 6 days
Delta
Delta
SAN
3:10a
MDW
10:22a
7h 12m
1 stop
MDW
10:40a
SAN
8:15p
9h 35m
1 stop
Depart: Sat Dec 31 2016 Return: Sat Jan 7 2017 Trip spans 8 days
Southwest
Southwest
SAN
6:10a
MDW
10:05a
3h 55m
nonstop
MDW
8:00a
SAN
12:20p
4h 20m
nonstop
Depart: Wed Jan 11 2017 Return: Sun Jan 15 2017 Trip spans 5 days
Delta
Delta
SAN
3:10a
MDW
1:02p
9h 52m
1 stop
MDW
10:40a
SAN
8:15p
9h 35m
1 stop
Depart: Thu Jan 12 2017 Return: Sun Jan 15 2017 Trip spans 4 days
Delta
Delta
SAN
6:52a
MDW
2:00p
7h 08m
1 stop
MDW
10:40a
SAN
8:15p
9h 35m
1 stop
Depart: Fri Jan 13 2017 Return: Sat Jan 14 2017 Trip spans 2 days
Delta
Delta
SAN
6:12a
MDW
3:46p
9h 34m
1 stop
MDW
8:45a
SAN
6:47p
10h 02m
1 stop
Depart: Wed Jan 18 2017 Return: Thu Jan 19 2017 Trip spans 2 days
Delta
Delta
SAN
1:25a
MDW
9:51a
8h 26m
1 stop
MDW
1:20a
SAN
8:12a
6h 52m
1 stop
Depart: Thu Jan 19 2017 Return: Sun Jan 22 2017 Trip spans 4 days
Delta
Delta
SAN
1:25a
MDW
9:51a
8h 26m
1 stop
MDW
3:30a
SAN
10:37a
7h 07m
1 stop
Depart: Fri Jan 20 2017 Return: Sun Jan 22 2017 Trip spans 3 days
Delta
Delta
SAN
2:15a
MDW
11:05a
8h 50m
1 stop
MDW
7:20a
SAN
5:55p
10h 35m
1 stop
Depart: Sat Jan 21 2017 Return: Mon Jan 23 2017 Trip spans 3 days
Delta
Delta
SAN
2:15a
MDW
9:09a
6h 54m
1 stop
MDW
4:24a
SAN
10:37a
6h 13m
1 stop
Depart: Wed Jan 25 2017 Return: Fri Jan 27 2017 Trip spans 3 days
Delta
Delta
SAN
1:25a
MDW
7:54a
6h 29m
1 stop
MDW
11:50a
SAN
7:48p
7h 58m
1 stop
Select an airline:  Southwest
Direct flights SAN to MDW on Southwest
Flight # Depart SAN Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
1073 6:20 am 12:20 pm Dec 25 - Dec 25
1360 6:20 am 12:25 pm Jan 5 - Mar 8
1391 6:20 am 12:20 pm Dec 17 - Dec 17
3275 6:20 am 12:30 pm Jan 3 - Jan 4
3275 6:20 am 12:30 pm Dec 6 - Dec 20
3894 6:30 am 12:30 pm Jan 1 - Jan 1
3894 6:30 am 12:30 pm Dec 11 - Dec 18
3269 6:40 am 12:45 pm Jan 7 - Mar 4
2265 6:45 am 12:45 pm Dec 24 - Dec 24
6812 6:45 am 12:45 pm Dec 31 - Dec 31
3058 6:50 am 12:50 pm Dec 21 - Jan 2
4901 7:10 am 1:10 pm Jan 8 - Jan 29
5433 9:00 am 2:50 pm Dec 17 - Dec 17
5434 10:50 am 4:45 pm Jan 7 - Mar 4
1173 11:10 am 5:05 pm Dec 24 - Dec 24
134 11:10 am 5:05 pm Jan 5 - Jan 13
6092 11:10 am 5:05 pm Dec 31 - Dec 31
4937 12:00 pm 5:55 pm Dec 21 - Jan 2
1122 12:15 pm 6:10 pm Dec 17 - Dec 17
5492 1:45 pm 7:40 pm Jan 7 - Mar 4
566 1:55 pm 7:45 pm Jan 1 - Jan 4
566 1:55 pm 7:45 pm Dec 6 - Dec 20
2296 2:25 pm 8:20 pm Dec 25 - Dec 25
1159 2:35 pm 8:25 pm Dec 24 - Dec 24
6050 2:35 pm 8:25 pm Dec 31 - Dec 31
1590 2:50 pm 8:45 pm Jan 5 - Jan 27
1120 3:05 pm 8:55 pm Dec 6 - Dec 20
1120 3:05 pm 8:55 pm Jan 1 - Jan 4
5484 3:35 pm 9:30 pm Jan 8 - Jan 29
4046 4:10 pm 10:00 pm Dec 21 - Jan 2
2197 4:25 pm 10:15 pm Dec 17 - Dec 17
3405 5:05 pm 10:55 pm Dec 25 - Dec 25
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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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Airports
Origin

San Diego
$212
Destination

Chicago
$212
Airlines Airline reviews

4 travelers who booked a flight from San Diego to Chicago rated their chosen airlines with an average of 7.5.

Overall
8.0
Boarding
7.5
Crew
8.0
Comfort
7.5
Food
6.5
Entertainment
5.5