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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: Wed Feb 18 2015 Return: Tue Feb 24 2015 Trip spans 7 days
Delta
Delta
SJC
5:55p
MDW
2:11a
8h 16m
1 stop
MDW
10:10a
SJC
6:44p
8h 34m
1 stop
Depart: Thu Feb 19 2015 Return: Tue Feb 24 2015 Trip spans 6 days
Delta
Delta
SJC
1:15a
MDW
7:40a
6h 25m
1 stop
MDW
12:03p
SJC
6:44p
6h 41m
1 stop
Depart: Fri Feb 20 2015 Return: Tue Feb 24 2015 Trip spans 5 days
Delta
Delta
SJC
5:55p
MDW
2:11a
8h 16m
1 stop
MDW
12:03p
SJC
6:44p
6h 41m
1 stop
Depart: Mon Feb 23 2015 Return: Thu Feb 26 2015 Trip spans 4 days
Delta
Delta
SJC
5:55p
MDW
2:11a
8h 16m
1 stop
MDW
9:06a
SJC
7:05p
9h 59m
1 stop
Depart: Tue Feb 24 2015 Return: Thu Feb 26 2015 Trip spans 3 days
Delta
Delta
SJC
1:15a
MDW
7:40a
6h 25m
1 stop
MDW
9:06a
SJC
7:05p
9h 59m
1 stop
Depart: Wed Feb 25 2015 Return: Fri Feb 27 2015 Trip spans 3 days
Delta
Delta
SJC
1:15a
MDW
9:33a
8h 18m
1 stop
MDW
9:06a
SJC
7:05p
9h 59m
1 stop
Depart: Thu Feb 26 2015 Return: Mon Mar 2 2015 Trip spans 5 days
Delta
Delta
SJC
1:15a
MDW
7:40a
6h 25m
1 stop
MDW
9:11a
SJC
6:53p
9h 42m
1 stop
Depart: Mon Mar 2 2015 Return: Wed Mar 4 2015 Trip spans 3 days
Delta
Delta
SJC
1:15a
MDW
7:37a
6h 22m
1 stop
MDW
7:56a
SJC
4:38p
8h 42m
1 stop
Depart: Tue Mar 3 2015 Return: Mon Mar 9 2015 Trip spans 6 days
Delta
Delta
SJC
1:15a
MDW
9:40a
8h 25m
1 stop
MDW
8:56a
SJC
5:38p
8h 42m
1 stop
Depart: Wed Mar 4 2015 Return: Mon Mar 9 2015 Trip spans 5 days
Delta
Delta
SJC
1:15a
MDW
7:37a
6h 22m
1 stop
MDW
8:56a
SJC
5:38p
8h 42m
1 stop
Depart: Thu Mar 5 2015 Return: Mon Mar 9 2015 Trip spans 4 days
Delta
Delta
SJC
1:15a
MDW
7:37a
6h 22m
1 stop
MDW
8:56a
SJC
5:38p
8h 42m
1 stop
Depart: Sat Mar 7 2015 Return: Mon Mar 9 2015 Trip spans 2 days
Delta
Delta
SJC
1:15a
MDW
7:36a
6h 21m
1 stop
MDW
8:56a
SJC
5:38p
8h 42m
1 stop
Depart: Mon Mar 9 2015 Return: Tue Mar 31 2015 Trip spans 23 days
Delta
Delta
SJC
2:15a
MDW
8:37a
6h 22m
1 stop
MDW
11:07a
SJC
5:38p
6h 31m
1 stop
Depart: Tue Mar 10 2015 Return: Tue Mar 17 2015 Trip spans 8 days
Delta
Delta
SJC
2:15a
MDW
8:37a
6h 22m
1 stop
MDW
11:07a
SJC
5:38p
6h 31m
1 stop
Depart: Wed Mar 11 2015 Return: Tue Mar 17 2015 Trip spans 7 days
Delta
Delta
SJC
2:15a
MDW
8:37a
6h 22m
1 stop
MDW
11:07a
SJC
5:38p
6h 31m
1 stop
Depart: Tue Mar 17 2015 Return: Tue Mar 24 2015 Trip spans 8 days
Delta
Delta
SJC
2:15a
MDW
8:37a
6h 22m
1 stop
MDW
11:07a
SJC
5:38p
6h 31m
1 stop
Depart: Wed Mar 18 2015 Return: Tue Mar 24 2015 Trip spans 7 days
Delta
Delta
SJC
2:15a
MDW
8:37a
6h 22m
1 stop
MDW
11:07a
SJC
5:38p
6h 31m
1 stop
Depart: Wed Mar 25 2015 Return: Tue Mar 31 2015 Trip spans 7 days
Delta
Delta
SJC
2:15a
MDW
8:37a
6h 22m
1 stop
MDW
11:07a
SJC
5:38p
6h 31m
1 stop
Depart: Wed Apr 15 2015 Return: Sat Apr 18 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: Sat Apr 18 2015 Return: Tue Apr 21 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
Change your search
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
1459 9:15 am 3:15 pm Mar 9 - Apr 6
1459 9:15 am 3:15 pm Mar 8 - Apr 5
1603 11:10 am 5:10 pm Mar 7 - Mar 7
3920 1:20 pm 7:30 pm Feb 21 - Feb 21
3920 1:20 pm 7:30 pm Feb 28 - Feb 28
3920 1:20 pm 7:30 pm Feb 14 - Feb 14
2606 2:10 pm 8:20 pm Jan 29 - Mar 6
Airports
Origin

San Jose
$246
Destination

Chicago
$246
Airlines