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Find Flight Deals 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: Fri Apr 17 2015 Return: Sat Apr 18 2015 Trip spans 2 days
Delta
Delta
SJC
6:45p
MDW
3:13a
8h 28m
1 stop
MDW
8:35a
SJC
8:53p
12h 18m
2 stops
Depart: Sat Apr 18 2015 Return: Tue Apr 21 2015 Trip spans 4 days
Delta
Delta
SJC
2:20a
MDW
8:36a
6h 16m
1 stop
MDW
8:55a
SJC
5:47p
8h 52m
1 stop
Depart: Tue Apr 21 2015 Return: Wed Apr 22 2015 Trip spans 2 days
Delta
Delta
SJC
2:20a
MDW
10:35a
8h 15m
1 stop
MDW
10:30a
SJC
7:36p
9h 06m
1 stop
Depart: Wed Apr 22 2015 Return: Fri Apr 24 2015 Trip spans 3 days
Delta
Delta
SJC
2:20a
MDW
8:37a
6h 17m
1 stop
MDW
8:55a
SJC
5:47p
8h 52m
1 stop
Depart: Sat Apr 25 2015 Return: Tue Apr 28 2015 Trip spans 4 days
Delta
Delta
SJC
2:20a
MDW
10:34a
8h 14m
1 stop
MDW
11:07a
SJC
5:47p
6h 40m
1 stop
Depart: Tue Apr 28 2015 Return: Sat May 2 2015 Trip spans 5 days
Delta
Delta
SJC
2:20a
MDW
10:35a
8h 15m
1 stop
MDW
11:12a
SJC
5:43p
6h 31m
1 stop
Depart: Wed Apr 29 2015 Return: Fri May 1 2015 Trip spans 3 days
Delta
Delta
SJC
2:20a
MDW
8:37a
6h 17m
1 stop
MDW
2:45a
SJC
9:46a
7h 01m
1 stop
Depart: Sat May 2 2015 Return: Tue May 5 2015 Trip spans 4 days
Delta
Delta
SJC
2:15a
MDW
8:41a
6h 26m
1 stop
MDW
11:12a
SJC
5:45p
6h 33m
1 stop
Depart: Sun May 3 2015 Return: Tue May 5 2015 Trip spans 3 days
Delta
Delta
SJC
2:15a
MDW
10:39a
8h 24m
1 stop
MDW
8:50a
SJC
5:45p
8h 55m
1 stop
Depart: Mon May 4 2015 Return: Fri May 8 2015 Trip spans 5 days
Delta
Delta
SJC
6:35p
MDW
3:23a
8h 48m
1 stop
MDW
2:45a
SJC
9:46a
7h 01m
1 stop
Depart: Tue May 5 2015 Return: Wed May 6 2015 Trip spans 2 days
Delta
Delta
SJC
2:15a
MDW
8:42a
6h 27m
1 stop
MDW
2:45a
SJC
9:46a
7h 01m
1 stop
Depart: Wed May 6 2015 Return: Fri May 8 2015 Trip spans 3 days
Delta
Delta
SJC
2:15a
MDW
8:42a
6h 27m
1 stop
MDW
2:45a
SJC
9:46a
7h 01m
1 stop
Depart: Sat May 23 2015 Return: Wed May 27 2015 Trip spans 5 days
Delta
Delta
SJC
2:15a
MDW
10:38a
8h 23m
1 stop
MDW
2:45a
SJC
9:46a
7h 01m
1 stop
Depart: Wed Aug 26 2015 Return: Wed Sep 2 2015 Trip spans 8 days
Delta
Delta
SJC
8:30a
MDW
2:53p
6h 23m
1 stop
MDW
2:45a
SJC
9:27a
6h 42m
1 stop
Depart: Mon May 25 2015 Return: Wed May 27 2015 Trip spans 3 days
Delta
Delta
SJC
2:15a
MDW
10:39a
8h 24m
1 stop
MDW
2:45a
SJC
9:46a
7h 01m
1 stop
Depart: Tue Apr 14 2015 Return: Tue Apr 21 2015 Trip spans 8 days
Delta
Delta
SJC
2:15a
MDW
10:35a
8h 20m
2 stops
MDW
11:07a
SJC
5:47p
6h 40m
1 stop
Depart: Wed Apr 15 2015 Return: Tue Apr 21 2015 Trip spans 7 days
Delta
Delta
SJC
2:20a
MDW
11:57a
9h 37m
2 stops
MDW
11:07a
SJC
5:47p
6h 40m
1 stop
Depart: Mon Apr 27 2015 Return: Sat May 2 2015 Trip spans 6 days
Delta
Delta
SJC
4:33p
MDW
2:38a
10h 05m
2 stops
MDW
11:12a
SJC
5:43p
6h 31m
1 stop
Depart: Wed May 27 2015 Return: Mon Jun 1 2015 Trip spans 6 days
Delta
Delta
SJC
6:35p
MDW
3:23a
8h 48m
1 stop
MDW
5:08a
SJC
3:56p
10h 48m
2 stops
Depart: Thu Apr 23 2015 Return: Sat Apr 25 2015 Trip spans 3 days
Delta
Delta
SJC
4:36p
MDW
2:38a
10h 02m
2 stops
MDW
11:07a
SJC
8:53p
9h 46m
2 stops
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 Apr 11 - May 16
1459 9:15 am 3:15 pm Mar 30 - Apr 6
3512 9:15 am 3:15 pm Apr 7 - Apr 7
4297 1:55 pm 8:05 pm Apr 8 - May 22
Airports
Origin

San Jose
$286
Destination

Chicago
$286
Airlines