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
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: Wed Apr 19 2017 Return: Mon Apr 24 2017 Trip spans 6 days
Delta
Delta
SAN
2:30a
MDW
10:52a
8h 22m
1 stop
MDW
1:27p
SAN
9:51p
8h 24m
1 stop
Depart: Fri Mar 24 2017 Return: Tue Mar 28 2017 Trip spans 5 days
Major Airline
Major Airline
SAN
1:00a
MDW
2:26a
1h 26m
nonstop
MDW
9:00a
SAN
2:26p
5h 26m
nonstop
Depart: Tue Mar 28 2017 Return: Tue Apr 11 2017 Trip spans 15 days
Delta
Delta
SAN
2:20a
MDW
11:25a
9h 05m
1 stop
MDW
12:46p
SAN
8:23p
7h 37m
1 stop
Depart: Mon Mar 27 2017 Return: Mon Apr 3 2017 Trip spans 8 days
Delta
Delta
SAN
3:00a
MDW
9:54a
6h 54m
1 stop
MDW
3:53p
SAN
9:51p
5h 58m
1 stop
Depart: Tue Apr 4 2017 Return: Tue Apr 11 2017 Trip spans 8 days
Delta
Delta
SAN
3:00a
MDW
12:00p
9h 00m
1 stop
MDW
3:53p
SAN
9:51p
5h 58m
1 stop
Depart: Tue Apr 11 2017 Return: Sat Apr 15 2017 Trip spans 5 days
Delta
Delta
SAN
4:19a
MDW
11:18a
6h 59m
1 stop
MDW
1:27p
SAN
7:52p
6h 25m
1 stop
Depart: Thu Mar 30 2017 Return: Tue Apr 18 2017 Trip spans 20 days
Major Airline
Major Airline
SAN
2:00a
MDW
3:26a
1h 26m
nonstop
MDW
2:00a
SAN
7:26a
5h 26m
nonstop
Depart: Wed Apr 12 2017 Return: Sat Apr 15 2017 Trip spans 4 days
Delta
Delta
SAN
9:00a
MDW
4:11p
7h 11m
1 stop
MDW
12:46p
SAN
8:18p
7h 32m
1 stop
Depart: Tue May 2 2017 Return: Sat May 6 2017 Trip spans 5 days
Delta
Delta
SAN
4:30a
MDW
10:57a
6h 27m
1 stop
MDW
11:20a
SAN
6:03p
6h 43m
1 stop
Depart: Sat Apr 29 2017 Return: Mon May 1 2017 Trip spans 3 days
Delta
Delta
SAN
3:00a
MDW
10:08a
7h 08m
1 stop
MDW
1:32p
SAN
9:47p
8h 15m
1 stop
Depart: Wed Mar 29 2017 Return: Mon Apr 3 2017 Trip spans 6 days
Delta
Delta
SAN
3:00a
MDW
12:10p
9h 10m
1 stop
MDW
3:53p
SAN
9:51p
5h 58m
1 stop
Depart: Mon Jun 26 2017 Return: Thu Jun 29 2017 Trip spans 4 days
Major Airline
Major Airline
SAN
2:00a
MDW
3:26a
1h 26m
1 stop
MDW
2:00a
SAN
7:26a
5h 26m
1 stop
Depart: Sat Apr 22 2017 Return: Sat Apr 29 2017 Trip spans 8 days
Delta
Delta
SAN
2:30a
MDW
10:51a
8h 21m
1 stop
MDW
11:52a
SAN
7:56p
8h 04m
1 stop
Depart: Wed Apr 26 2017 Return: Mon May 1 2017 Trip spans 6 days
Delta
Delta
SAN
4:45a
MDW
1:16p
8h 31m
1 stop
MDW
3:50p
SAN
9:47p
5h 57m
1 stop
Depart: Sat May 13 2017 Return: Tue May 16 2017 Trip spans 4 days
Delta
Delta
SAN
4:10a
MDW
11:15a
7h 05m
1 stop
MDW
3:50p
SAN
9:47p
5h 57m
1 stop
Depart: Wed May 31 2017 Return: Tue Jun 6 2017 Trip spans 7 days
Delta
Delta
SAN
7:26a
MDW
4:10p
8h 44m
1 stop
MDW
2:30a
SAN
11:36a
9h 06m
1 stop
Depart: Sat May 20 2017 Return: Tue May 23 2017 Trip spans 4 days
Delta
Delta
SAN
2:40a
MDW
10:55a
8h 15m
1 stop
MDW
2:30a
SAN
11:36a
9h 06m
1 stop
Depart: Sat Jun 3 2017 Return: Tue Jun 6 2017 Trip spans 4 days
Delta
Delta
SAN
2:40a
MDW
10:55a
8h 15m
1 stop
MDW
2:30a
SAN
11:36a
9h 06m
1 stop
Depart: Fri Apr 14 2017 Return: Mon Apr 17 2017 Trip spans 4 days
Delta
Delta
SAN
3:00a
MDW
12:00p
9h 00m
1 stop
MDW
3:53p
SAN
9:51p
5h 58m
1 stop
Depart: Sun Apr 16 2017 Return: Sat Apr 22 2017 Trip spans 7 days
Delta
Delta
SAN
2:30a
MDW
8:35a
6h 05m
1 stop
MDW
11:10a
SAN
6:02p
6h 52m
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
2407 6:45 am 12:40 pm Mar 25 - Apr 22
1528 6:50 am 12:45 pm Mar 20 - Apr 24
1315 6:55 am 12:50 pm Apr 25 - Jun 2
1559 7:00 am 12:55 pm Apr 29 - Jun 3
4604 7:05 am 12:55 pm Mar 26 - Apr 23
4632 7:15 am 1:10 pm Apr 30 - May 21
4311 8:50 am 2:45 pm Apr 30 - May 21
2553 11:00 am 4:50 pm Mar 25 - Apr 22
1848 11:05 am 5:00 pm Apr 25 - May 26
3966 11:10 am 5:00 pm Mar 26 - Apr 23
4651 11:30 am 5:20 pm Apr 29 - May 27
1760 11:35 am 5:25 pm Mar 20 - Apr 24
941 1:05 pm 6:55 pm Apr 25 - Jun 2
3349 1:30 pm 7:20 pm Apr 30 - May 21
5575 2:05 pm 7:55 pm Mar 26 - Apr 23
4891 2:15 pm 8:05 pm Mar 25 - Apr 22
5111 2:20 pm 8:10 pm Apr 29 - May 6
1104 2:40 pm 8:30 pm Mar 20 - Apr 24
3520 2:50 pm 8:40 pm Apr 25 - Jun 2
4688 3:05 pm 8:55 pm Apr 30 - May 7
5251 3:35 pm 9:30 pm Mar 26 - Apr 23
1625 6:30 pm 12:20 am Mar 20 - Apr 24
4976 6:55 pm 12:45 am Mar 25 - Apr 22
* 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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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

San Diego
$244
Destination

Chicago
$244
Airlines