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

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

Book cheap flights from San Jose to Chicago Midway

(Round-trip)
Depart: Tue Aug 25 2015 Return: Tue Sep 1 2015 Trip spans 8 days
Delta
Delta
SJC
12:29p
MDW
6:03p
5h 34m
1 stop
MDW
11:27a
SJC
7:37p
8h 10m
1 stop
Depart: Wed Aug 26 2015 Return: Tue Sep 1 2015 Trip spans 7 days
Delta
Delta
SJC
9:30a
MDW
6:03p
8h 33m
1 stop
MDW
8:55a
SJC
5:46p
8h 51m
1 stop
Depart: Sat Aug 29 2015 Return: Wed Sep 2 2015 Trip spans 5 days
Delta
Delta
SJC
2:30a
MDW
10:43a
8h 13m
1 stop
MDW
8:30a
SJC
7:37p
11h 07m
1 stop
Depart: Thu Sep 3 2015 Return: Sun Sep 6 2015 Trip spans 4 days
Delta
Delta
SJC
9:20a
MDW
5:56p
8h 36m
1 stop
MDW
9:50a
SJC
7:37p
9h 47m
1 stop
Depart: Wed Oct 28 2015 Return: Sat Oct 31 2015 Trip spans 4 days
Delta
Delta
SJC
8:30a
MDW
2:53p
6h 23m
1 stop
MDW
11:10a
SJC
5:46p
6h 36m
1 stop
Depart: Thu Nov 5 2015 Return: Wed Nov 11 2015 Trip spans 7 days
Delta
Delta
SJC
1:29a
MDW
9:51a
8h 22m
1 stop
MDW
1:45a
SJC
8:27a
6h 42m
1 stop
Depart: Sun Sep 6 2015 Return: Sat Sep 19 2015 Trip spans 14 days
Delta
Delta
SJC
2:29a
MDW
10:51a
8h 22m
1 stop
MDW
8:55a
SJC
8:05p
11h 10m
2 stops
Depart: Sat Sep 12 2015 Return: Mon Sep 14 2015 Trip spans 3 days
Delta
Delta
SJC
2:29a
MDW
8:30a
6h 01m
1 stop
MDW
11:10a
SJC
8:05p
8h 55m
2 stops
Depart: Tue Sep 15 2015 Return: Sat Sep 19 2015 Trip spans 5 days
Delta
Delta
SJC
12:30p
MDW
5:56p
5h 26m
1 stop
MDW
8:30a
SJC
6:06p
9h 36m
2 stops
Depart: Sat Oct 3 2015 Return: Tue Oct 6 2015 Trip spans 4 days
Delta
Delta
SJC
2:29a
MDW
10:51a
8h 22m
1 stop
MDW
2:43a
SJC
11:45a
9h 02m
2 stops
Depart: Fri Nov 6 2015 Return: Mon Nov 9 2015 Trip spans 4 days
Delta
Delta
SJC
3:30a
MDW
11:47a
8h 17m
2 stops
MDW
4:05a
SJC
1:00p
8h 55m
2 stops
Depart: Mon Aug 31 2015 Return: Tue Sep 8 2015 Trip spans 9 days
Delta
Delta
SJC
12:29p
MDW
6:03p
5h 34m
1 stop
MDW
8:30a
SJC
7:37p
11h 07m
1 stop
Depart: Tue Sep 29 2015 Return: Mon Oct 5 2015 Trip spans 7 days
Delta
Delta
SJC
2:29a
MDW
10:51a
8h 22m
1 stop
MDW
8:30a
SJC
7:37p
11h 07m
1 stop
Depart: Wed Sep 30 2015 Return: Mon Oct 5 2015 Trip spans 6 days
Delta
Delta
SJC
2:29a
MDW
10:51a
8h 22m
1 stop
MDW
11:27a
SJC
7:37p
8h 10m
1 stop
Depart: Tue Oct 6 2015 Return: Sat Oct 10 2015 Trip spans 5 days
Delta
Delta
SJC
12:30p
MDW
5:56p
5h 26m
1 stop
MDW
11:10a
SJC
5:46p
6h 36m
1 stop
Depart: Wed Oct 7 2015 Return: Sat Oct 10 2015 Trip spans 4 days
Delta
Delta
SJC
2:29a
MDW
8:30a
6h 01m
1 stop
MDW
11:10a
SJC
5:46p
6h 36m
1 stop
Depart: Fri Oct 2 2015 Return: Mon Oct 5 2015 Trip spans 4 days
Delta
Delta
SJC
10:20a
MDW
5:56p
7h 36m
2 stops
MDW
11:10a
SJC
8:05p
8h 55m
2 stops
Depart: Fri Jun 5 2015 Return: Tue Jun 9 2015 Trip spans 5 days
Delta
Delta
SJC
8:30a
MDW
3:49p
7h 19m
1 stop
MDW
2:35a
SJC
9:16a
6h 41m
1 stop
Depart: Sat Jun 6 2015 Return: Tue Jun 9 2015 Trip spans 4 days
Delta
Delta
SJC
8:30a
MDW
3:27p
6h 57m
1 stop
MDW
9:00a
SJC
5:47p
8h 47m
1 stop
Depart: Tue Jun 9 2015 Return: Sat Jun 13 2015 Trip spans 5 days
Delta
Delta
SJC
8:30a
MDW
3:28p
6h 58m
1 stop
MDW
2:35a
SJC
9:15a
6h 40m
1 stop
Select an airline:  Southwest
Direct flights SJC to MDW on Southwest
Flight # Depart SJC Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
1171 6:30 am 12:45 pm May 30 - Jun 6
34 1:20 pm 7:30 pm Jun 13 - Jun 27
147 1:30 pm 7:40 pm Jul 4 - Jul 4
2525 3:15 pm 9:30 pm Jun 7 - Aug 7
Airports
Origin

San Jose
$286
Destination

Chicago
$286
Airlines