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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 Sep 1 2015 Return: Wed Sep 30 2015 Trip spans 30 days
Delta
Delta
SJC
2:45a
MDW
8:41a
5h 56m
1 stop
MDW
11:20a
SJC
7:38p
8h 18m
1 stop
Depart: Wed Sep 9 2015 Return: Mon Sep 14 2015 Trip spans 6 days
Delta
Delta
SJC
6:45p
MDW
3:49a
9h 04m
1 stop
MDW
11:20a
SJC
7:38p
8h 18m
1 stop
Depart: Sat Sep 12 2015 Return: Mon Sep 14 2015 Trip spans 3 days
Delta
Delta
SJC
2:45a
MDW
8:40a
5h 55m
1 stop
MDW
9:50a
SJC
7:38p
9h 48m
1 stop
Depart: Tue Sep 15 2015 Return: Thu Sep 17 2015 Trip spans 3 days
Delta
Delta
SJC
12:30p
MDW
6:06p
5h 36m
1 stop
MDW
9:50a
SJC
7:38p
9h 48m
1 stop
Depart: Wed Sep 16 2015 Return: Mon Sep 21 2015 Trip spans 6 days
Delta
Delta
SJC
9:25a
MDW
6:06p
8h 41m
1 stop
MDW
9:50a
SJC
7:38p
9h 48m
1 stop
Depart: Wed Sep 23 2015 Return: Thu Sep 24 2015 Trip spans 2 days
Delta
Delta
SJC
6:45p
MDW
3:18a
8h 33m
1 stop
MDW
9:50a
SJC
7:38p
9h 48m
1 stop
Depart: Sat Oct 3 2015 Return: Tue Oct 6 2015 Trip spans 4 days
Delta
Delta
SJC
12:30p
MDW
6:07p
5h 37m
1 stop
MDW
2:35a
SJC
9:10a
6h 35m
1 stop
Depart: Wed Oct 7 2015 Return: Wed Oct 14 2015 Trip spans 8 days
Delta
Delta
SJC
2:30a
MDW
8:40a
6h 10m
1 stop
MDW
9:50a
SJC
7:48p
9h 58m
1 stop
Depart: Tue Oct 13 2015 Return: Thu Oct 15 2015 Trip spans 3 days
Delta
Delta
SJC
2:30a
MDW
8:40a
6h 10m
1 stop
MDW
9:50a
SJC
7:48p
9h 58m
1 stop
Depart: Sat Oct 17 2015 Return: Wed Oct 21 2015 Trip spans 5 days
Delta
Delta
SJC
2:30a
MDW
10:32a
8h 02m
1 stop
MDW
11:20a
SJC
7:48p
8h 28m
1 stop
Depart: Sat Oct 31 2015 Return: Tue Nov 3 2015 Trip spans 4 days
Delta
Delta
SJC
2:29a
MDW
10:51a
8h 22m
1 stop
MDW
10:10a
SJC
4:46p
6h 36m
1 stop
Depart: Thu Sep 10 2015 Return: Mon Sep 14 2015 Trip spans 5 days
Delta
Delta
SJC
6:46a
MDW
6:06p
11h 20m
2 stops
MDW
9:50a
SJC
7:38p
9h 48m
1 stop
Depart: Thu Sep 17 2015 Return: Tue Sep 22 2015 Trip spans 6 days
Delta
Delta
SJC
4:10a
MDW
2:27p
10h 17m
2 stops
MDW
9:50a
SJC
7:38p
9h 48m
1 stop
Depart: Fri Oct 9 2015 Return: Sat Oct 10 2015 Trip spans 2 days
Delta
Delta
SJC
6:55p
MDW
3:52a
8h 57m
1 stop
MDW
8:30a
SJC
7:53p
11h 23m
2 stops
Depart: Thu Oct 15 2015 Return: Mon Oct 19 2015 Trip spans 5 days
Delta
Delta
SJC
6:52a
MDW
6:07p
11h 15m
2 stops
MDW
2:30a
SJC
1:50p
11h 20m
2 stops
Depart: Tue Aug 18 2015 Return: Tue Aug 25 2015 Trip spans 8 days
Delta
Delta
SJC
2:30a
MDW
8:44a
6h 14m
1 stop
MDW
11:20a
SJC
5:38p
6h 18m
1 stop
Depart: Sat Aug 22 2015 Return: Tue Aug 25 2015 Trip spans 4 days
Delta
Delta
SJC
9:28a
MDW
6:03p
8h 35m
1 stop
MDW
11:20a
SJC
5:38p
6h 18m
1 stop
Depart: Sun Sep 6 2015 Return: Wed Sep 9 2015 Trip spans 4 days
Delta
Delta
SJC
2:45a
MDW
8:41a
5h 56m
1 stop
MDW
8:58a
SJC
5:40p
8h 42m
1 stop
Depart: Fri Sep 18 2015 Return: Mon Sep 21 2015 Trip spans 4 days
Delta
Delta
SJC
6:45p
MDW
3:12a
8h 27m
1 stop
MDW
9:50a
SJC
7:38p
9h 48m
1 stop
Depart: Tue Sep 22 2015 Return: Wed Sep 30 2015 Trip spans 9 days
Delta
Delta
SJC
8:30a
MDW
3:09p
6h 39m
1 stop
MDW
8:58a
SJC
5:40p
8h 42m
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
173 1:20 pm 7:30 pm Aug 8 - Aug 8
34 1:20 pm 7:30 pm Jul 11 - Aug 1
2071 2:55 pm 9:05 pm Aug 9 - Sep 4
2525 3:15 pm 9:30 pm Jun 28 - Aug 7
Airports
Origin

San Jose
$284
Destination

Chicago
$284
Airlines