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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: Thu Aug 27 2015 Return: Tue Sep 1 2015 Trip spans 6 days
Delta
Delta
MDW
2:40a
SJC
10:08a
7h 28m
1 stop
SJC
8:30a
MDW
3:09p
6h 39m
1 stop
Depart: Tue Sep 1 2015 Return: Sat Sep 5 2015 Trip spans 5 days
Delta
Delta
MDW
2:35a
SJC
9:10a
6h 35m
1 stop
SJC
2:45a
MDW
10:40a
7h 55m
1 stop
Depart: Wed Sep 2 2015 Return: Sat Sep 5 2015 Trip spans 4 days
Delta
Delta
MDW
8:58a
SJC
5:40p
8h 42m
1 stop
SJC
2:45a
MDW
10:45a
8h 00m
1 stop
Depart: Sat Sep 5 2015 Return: Wed Sep 9 2015 Trip spans 5 days
Delta
Delta
MDW
11:11a
SJC
5:38p
6h 27m
1 stop
SJC
9:25a
MDW
6:06p
8h 41m
1 stop
Depart: Wed Sep 9 2015 Return: Sat Sep 19 2015 Trip spans 11 days
Delta
Delta
MDW
9:50a
SJC
7:38p
9h 48m
1 stop
SJC
12:30p
MDW
6:06p
5h 36m
1 stop
Depart: Thu Sep 10 2015 Return: Mon Sep 14 2015 Trip spans 5 days
Delta
Delta
MDW
9:50a
SJC
7:38p
9h 48m
1 stop
SJC
6:45p
MDW
3:18a
8h 33m
1 stop
Depart: Tue Sep 15 2015 Return: Sat Sep 19 2015 Trip spans 5 days
Delta
Delta
MDW
2:35a
SJC
9:10a
6h 35m
1 stop
SJC
2:45a
MDW
8:40a
5h 55m
1 stop
Depart: Thu Sep 17 2015 Return: Mon Sep 21 2015 Trip spans 5 days
Delta
Delta
MDW
9:50a
SJC
7:38p
9h 48m
1 stop
SJC
6:45p
MDW
3:18a
8h 33m
1 stop
Depart: Tue Sep 22 2015 Return: Sat Sep 26 2015 Trip spans 5 days
Delta
Delta
MDW
9:50a
SJC
7:38p
9h 48m
1 stop
SJC
12:30p
MDW
6:06p
5h 36m
1 stop
Depart: Thu Sep 24 2015 Return: Mon Sep 28 2015 Trip spans 5 days
Delta
Delta
MDW
9:50a
SJC
7:38p
9h 48m
1 stop
SJC
6:45p
MDW
3:18a
8h 33m
1 stop
Depart: Sat Sep 26 2015 Return: Wed Sep 30 2015 Trip spans 5 days
Delta
Delta
MDW
11:11a
SJC
5:38p
6h 27m
1 stop
SJC
12:30p
MDW
6:06p
5h 36m
1 stop
Depart: Tue Sep 29 2015 Return: Sat Oct 3 2015 Trip spans 5 days
Delta
Delta
MDW
11:20a
SJC
7:38p
8h 18m
1 stop
SJC
12:30p
MDW
6:07p
5h 37m
1 stop
Depart: Wed Sep 30 2015 Return: Wed Oct 7 2015 Trip spans 8 days
Delta
Delta
MDW
9:50a
SJC
7:38p
9h 48m
1 stop
SJC
9:25a
MDW
6:07p
8h 42m
1 stop
Depart: Thu Oct 1 2015 Return: Mon Oct 5 2015 Trip spans 5 days
Delta
Delta
MDW
9:50a
SJC
7:48p
9h 58m
1 stop
SJC
6:55p
MDW
3:52a
8h 57m
1 stop
Depart: Tue Oct 6 2015 Return: Tue Oct 13 2015 Trip spans 8 days
Delta
Delta
MDW
2:35a
SJC
9:10a
6h 35m
1 stop
SJC
2:30a
MDW
8:40a
6h 10m
1 stop
Depart: Wed Oct 7 2015 Return: Wed Oct 14 2015 Trip spans 8 days
Delta
Delta
MDW
9:50a
SJC
7:48p
9h 58m
1 stop
SJC
2:30a
MDW
8:40a
6h 10m
1 stop
Depart: Thu Oct 15 2015 Return: Wed Oct 21 2015 Trip spans 7 days
Delta
Delta
MDW
9:50a
SJC
7:48p
9h 58m
1 stop
SJC
8:30a
MDW
3:10p
6h 40m
1 stop
Depart: Wed Nov 11 2015 Return: Tue Nov 17 2015 Trip spans 7 days
Delta
Delta
MDW
10:10a
SJC
4:46p
6h 36m
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
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
1958 7:00 pm 9:30 pm Jul 11 - Aug 8
485 8:10 pm 10:50 pm Jul 10 - Aug 7
485 8:10 pm 10:50 pm Jun 28 - Jul 9
Airports
Origin

Chicago
$284
Destination

San Jose
$284
Airlines