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Find Deals on Flights from Chicago Midway to San Jose (MDW - SJC)

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago Midway to San Jose

(Round-trip)
Depart: Sat Aug 22 2015 Return: Tue Aug 25 2015 Trip spans 4 days
Delta
Delta
MDW
2:30a
SJC
9:09a
6h 39m
1 stop
SJC
12:29p
MDW
6:03p
5h 34m
1 stop
Depart: Wed Sep 2 2015 Return: Sun Sep 6 2015 Trip spans 5 days
Delta
Delta
MDW
2:43a
SJC
10:34a
7h 51m
1 stop
SJC
2:29a
MDW
10:51a
8h 22m
1 stop
Depart: Thu Sep 3 2015 Return: Sun Sep 6 2015 Trip spans 4 days
Delta
Delta
MDW
8:55a
SJC
5:46p
8h 51m
1 stop
SJC
2:29a
MDW
8:30a
6h 01m
1 stop
Depart: Sat Sep 5 2015 Return: Sun Sep 6 2015 Trip spans 2 days
Delta
Delta
MDW
11:10a
SJC
5:46p
6h 36m
1 stop
SJC
2:29a
MDW
8:30a
6h 01m
1 stop
Depart: Tue Sep 29 2015 Return: Sat Oct 3 2015 Trip spans 5 days
Delta
Delta
MDW
9:50a
SJC
7:37p
9h 47m
1 stop
SJC
12:30p
MDW
5:56p
5h 26m
1 stop
Depart: Wed Oct 7 2015 Return: Sat Oct 17 2015 Trip spans 11 days
Delta
Delta
MDW
2:43a
SJC
10:34a
7h 51m
1 stop
SJC
2:29a
MDW
8:30a
6h 01m
1 stop
Depart: Wed Oct 28 2015 Return: Mon Nov 2 2015 Trip spans 6 days
Delta
Delta
MDW
8:30a
SJC
7:37p
11h 07m
1 stop
SJC
1:29a
MDW
7:30a
6h 01m
1 stop
Depart: Wed Nov 4 2015 Return: Wed Nov 11 2015 Trip spans 8 days
Delta
Delta
MDW
1:43a
SJC
9:34a
7h 51m
1 stop
SJC
11:30a
MDW
4:56p
5h 26m
1 stop
Depart: Fri Nov 6 2015 Return: Mon Nov 9 2015 Trip spans 4 days
Delta
Delta
MDW
7:55a
SJC
4:46p
8h 51m
1 stop
SJC
11:30a
MDW
4:56p
5h 26m
1 stop
Depart: Sat Nov 7 2015 Return: Tue Nov 10 2015 Trip spans 4 days
Delta
Delta
MDW
10:10a
SJC
4:46p
6h 36m
1 stop
SJC
11:30a
MDW
4:56p
5h 26m
1 stop
Depart: Wed Nov 11 2015 Return: Tue Nov 17 2015 Trip spans 7 days
Delta
Delta
MDW
1:45a
SJC
8:27a
6h 42m
1 stop
SJC
11:30a
MDW
4:56p
5h 26m
1 stop
Depart: Thu Nov 12 2015 Return: Tue Nov 17 2015 Trip spans 6 days
Delta
Delta
MDW
1:45a
SJC
8:27a
6h 42m
1 stop
SJC
11:30a
MDW
4:56p
5h 26m
1 stop
Depart: Sat Nov 14 2015 Return: Tue Nov 17 2015 Trip spans 4 days
Delta
Delta
MDW
10:10a
SJC
4:46p
6h 36m
1 stop
SJC
11:30a
MDW
4:56p
5h 26m
1 stop
Depart: Mon Nov 23 2015 Return: Fri Nov 27 2015 Trip spans 5 days
Delta
Delta
MDW
7:55a
SJC
4:46p
8h 51m
1 stop
SJC
7:30a
MDW
1:53p
6h 23m
1 stop
Depart: Fri Aug 28 2015 Return: Tue Sep 1 2015 Trip spans 5 days
Delta
Delta
MDW
2:40a
SJC
12:23p
9h 43m
2 stops
SJC
9:20a
MDW
5:56p
8h 36m
1 stop
Depart: Wed Sep 23 2015 Return: Tue Sep 29 2015 Trip spans 7 days
Delta
Delta
MDW
5:05a
SJC
1:47p
8h 42m
2 stops
SJC
6:35p
MDW
3:04a
8h 29m
1 stop
Depart: Tue Oct 13 2015 Return: Tue Oct 20 2015 Trip spans 8 days
Delta
Delta
MDW
2:43a
SJC
11:45a
9h 02m
2 stops
SJC
12:30p
MDW
5:56p
5h 26m
1 stop
Depart: Sat Oct 17 2015 Return: Sat Oct 24 2015 Trip spans 8 days
Delta
Delta
MDW
8:55a
SJC
8:05p
11h 10m
2 stops
SJC
2:29a
MDW
8:30a
6h 01m
1 stop
Depart: Fri Oct 23 2015 Return: Mon Oct 26 2015 Trip spans 4 days
Delta
Delta
MDW
2:43a
SJC
11:45a
9h 02m
2 stops
SJC
12:30p
MDW
5:56p
5h 26m
1 stop
Depart: Wed Jun 3 2015 Return: Tue Jun 9 2015 Trip spans 7 days
Delta
Delta
MDW
8:50a
SJC
5:45p
8h 55m
1 stop
SJC
2:30a
MDW
10:46a
8h 16m
1 stop
Select an airline:  Southwest
Direct flights MDW to SJC on Southwest
Flight # Depart MDW Arrive SJC Sun Mon Tue Wed Thu Fri Sat Valid Between
15 7:00 pm 9:35 pm Jun 6 - Jun 6
1958 7:00 pm 9:30 pm Jun 13 - Jun 27
1987 7:00 pm 9:30 pm Jul 4 - Jul 4
1550 7:30 pm 10:05 pm May 31 - Jun 5
485 8:10 pm 10:50 pm Jun 7 - Jul 2
485 8:10 pm 10:50 pm Jul 5 - Aug 7
1760 8:15 pm 10:55 pm Jul 3 - Jul 3
Airports
Origin

Chicago
$286
Destination

San Jose
$286
Airlines