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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 Jan 7 2015 Return: Fri Jan 9 2015 Trip spans 3 days
Delta
Delta
SJC
1:25a
MDW
9:52a
8h 27m
1 stop
MDW
12:27p
SJC
6:38p
6h 11m
1 stop
Depart: Fri Jan 9 2015 Return: Wed Jan 14 2015 Trip spans 6 days
Delta
Delta
SJC
1:25a
MDW
9:52a
8h 27m
1 stop
MDW
8:40a
SJC
7:21p
10h 41m
1 stop
Depart: Mon Jan 12 2015 Return: Tue Jan 13 2015 Trip spans 2 days
Delta
Delta
SJC
1:25a
MDW
9:52a
8h 27m
1 stop
MDW
12:27p
SJC
6:38p
6h 11m
1 stop
Depart: Tue Jan 13 2015 Return: Tue Jan 20 2015 Trip spans 8 days
Delta
Delta
SJC
1:25a
MDW
7:36a
6h 11m
1 stop
MDW
12:27p
SJC
6:38p
6h 11m
1 stop
Depart: Wed Jan 14 2015 Return: Fri Jan 16 2015 Trip spans 3 days
Delta
Delta
SJC
6:03p
MDW
4:29a
10h 26m
1 stop
MDW
8:40a
SJC
7:21p
10h 41m
1 stop
Depart: Thu Jan 15 2015 Return: Tue Jan 20 2015 Trip spans 6 days
Delta
Delta
SJC
1:25a
MDW
7:36a
6h 11m
1 stop
MDW
10:06a
SJC
6:38p
8h 32m
1 stop
Depart: Sat Jan 17 2015 Return: Fri Jan 23 2015 Trip spans 7 days
Delta
Delta
SJC
3:30a
MDW
10:01a
6h 31m
1 stop
MDW
12:27p
SJC
6:38p
6h 11m
1 stop
Depart: Tue Jan 20 2015 Return: Fri Jan 23 2015 Trip spans 4 days
Delta
Delta
SJC
1:25a
MDW
7:36a
6h 11m
1 stop
MDW
12:27p
SJC
6:38p
6h 11m
1 stop
Depart: Wed Jan 21 2015 Return: Thu Jan 22 2015 Trip spans 2 days
Delta
Delta
SJC
1:25a
MDW
7:36a
6h 11m
1 stop
MDW
10:20a
SJC
7:21p
9h 01m
1 stop
Depart: Thu Jan 22 2015 Return: Fri Jan 23 2015 Trip spans 2 days
Delta
Delta
SJC
1:25a
MDW
7:36a
6h 11m
1 stop
MDW
12:27p
SJC
6:38p
6h 11m
1 stop
Depart: Mon Jan 26 2015 Return: Fri Jan 30 2015 Trip spans 5 days
Delta
Delta
SJC
1:25a
MDW
7:36a
6h 11m
1 stop
MDW
8:40a
SJC
7:21p
10h 41m
1 stop
Depart: Wed Jan 28 2015 Return: Mon Feb 2 2015 Trip spans 6 days
Delta
Delta
SJC
1:25a
MDW
7:36a
6h 11m
1 stop
MDW
10:20a
SJC
7:21p
9h 01m
1 stop
Depart: Wed Feb 4 2015 Return: Fri Feb 6 2015 Trip spans 3 days
Delta
Delta
SJC
1:25a
MDW
9:52a
8h 27m
1 stop
MDW
10:20a
SJC
7:21p
9h 01m
1 stop
Depart: Tue Feb 17 2015 Return: Wed Feb 18 2015 Trip spans 2 days
Delta
Delta
SJC
1:29a
MDW
7:30a
6h 01m
1 stop
MDW
12:10p
SJC
6:31p
6h 21m
1 stop
Depart: Wed Feb 18 2015 Return: Tue Feb 24 2015 Trip spans 7 days
Delta
Delta
SJC
1:29a
MDW
7:30a
6h 01m
1 stop
MDW
12:10p
SJC
6:31p
6h 21m
1 stop
Depart: Thu Feb 19 2015 Return: Tue Feb 24 2015 Trip spans 6 days
Delta
Delta
SJC
1:29a
MDW
7:30a
6h 01m
1 stop
MDW
12:10p
SJC
6:31p
6h 21m
1 stop
Depart: Sat Feb 21 2015 Return: Tue Feb 24 2015 Trip spans 4 days
Delta
Delta
SJC
1:29a
MDW
7:30a
6h 01m
1 stop
MDW
12:10p
SJC
6:31p
6h 21m
1 stop
Depart: Tue Apr 14 2015 Return: Sat Apr 18 2015 Trip spans 5 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
10:51a
8h 22m
1 stop
MDW
11:10a
SJC
5:46p
6h 36m
1 stop
Depart: Sat May 16 2015 Return: Sat May 30 2015 Trip spans 15 days
Delta
Delta
SJC
2:29a
MDW
10:51a
8h 22m
1 stop
MDW
8:10a
SJC
5:46p
9h 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
3920 1:20 pm 7:30 pm Jan 10 - Feb 7
2606 2:10 pm 8:20 pm Jan 6 - Mar 6
3413 2:15 pm 8:25 pm Dec 29 - Jan 5
878 2:15 pm 8:25 pm Dec 28 - Dec 28
878 2:15 pm 8:25 pm Dec 20 - Dec 27
3443 2:20 pm 8:30 pm Dec 31 - Dec 31
Airports
Origin

San Jose
$246
Destination

Chicago
$246
Airlines