Find Deals on Flights from San Jose to Chicago Midway (SJC - MDW)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from San Jose to Chicago Midway

(Round-trip)
Depart: Wed Sep 14 2016 Return: Tue Sep 20 2016 Trip spans 7 days
Delta
Delta
SJC
2:30a
MDW
10:43a
8h 13m
1 stop
MDW
11:30a
SJC
7:34p
8h 04m
1 stop
Depart: Sat Aug 6 2016 Return: Wed Aug 10 2016 Trip spans 5 days
Southwest
Southwest
SJC
1:15p
MDW
7:00p
5h 45m
1 stop
MDW
3:00a
SJC
9:05a
6h 05m
1 stop
Depart: Mon Jun 13 2016 Return: Fri Jun 17 2016 Trip spans 5 days
Major Airline
Major Airline
SJC
12:17p
MDW
2:42a
14h 25m
2 stops
MDW
8:57a
SJC
6:00p
9h 03m
1 stop
Depart: Wed May 11 2016 Return: Wed May 18 2016 Trip spans 8 days
Delta
Delta
SJC
2:20a
MDW
10:44a
8h 24m
1 stop
MDW
11:34a
SJC
7:48p
8h 14m
1 stop
Depart: Tue Jun 7 2016 Return: Tue Jun 14 2016 Trip spans 8 days
Southwest
Southwest
SJC
10:05a
MDW
2:10p
4h 05m
nonstop
MDW
3:40a
SJC
8:10a
4h 30m
nonstop
Depart: Mon May 16 2016 Return: Wed May 18 2016 Trip spans 3 days
Delta
Delta
SJC
8:30a
MDW
3:27p
6h 57m
1 stop
MDW
9:55a
SJC
7:48p
9h 53m
1 stop
Depart: Tue May 17 2016 Return: Wed May 18 2016 Trip spans 2 days
Delta
Delta
SJC
8:30a
MDW
3:27p
6h 57m
1 stop
MDW
9:55a
SJC
7:48p
9h 53m
1 stop
Depart: Tue Jul 5 2016 Return: Mon Jul 11 2016 Trip spans 7 days
Southwest
Southwest
SJC
1:35p
MDW
7:50p
6h 15m
1 stop
MDW
2:00p
SJC
8:55p
6h 55m
1 stop
Depart: Wed May 18 2016 Return: Thu May 19 2016 Trip spans 2 days
Delta
Delta
SJC
2:20a
MDW
8:42a
6h 22m
1 stop
MDW
2:30a
SJC
9:28a
6h 58m
1 stop
Depart: Wed Jul 13 2016 Return: Tue Jul 19 2016 Trip spans 7 days
Southwest
Southwest
SJC
1:35p
MDW
7:50p
6h 15m
1 stop
MDW
2:00p
SJC
8:55p
6h 55m
1 stop
Depart: Sat May 21 2016 Return: Sun May 29 2016 Trip spans 9 days
Delta
Delta
SJC
2:20a
MDW
10:43a
8h 23m
1 stop
MDW
8:59a
SJC
5:46p
8h 47m
1 stop
Depart: Mon Jul 25 2016 Return: Tue Aug 2 2016 Trip spans 9 days
Southwest
Southwest
SJC
1:35p
MDW
7:50p
6h 15m
1 stop
MDW
2:00p
SJC
8:55p
6h 55m
1 stop
Depart: Sat Jun 4 2016 Return: Sat Jun 11 2016 Trip spans 8 days
Delta
Delta
SJC
2:20a
MDW
10:43a
8h 23m
1 stop
MDW
11:14a
SJC
5:57p
6h 43m
1 stop
Depart: Thu Aug 4 2016 Return: Tue Aug 16 2016 Trip spans 13 days
Southwest
Southwest
SJC
1:35p
MDW
7:50p
6h 15m
1 stop
MDW
2:10a
SJC
8:05a
5h 55m
1 stop
Depart: Mon Sep 26 2016 Return: Thu Sep 29 2016 Trip spans 4 days
Delta
Delta
SJC
8:36a
MDW
4:13p
7h 37m
1 stop
MDW
9:47a
SJC
7:34p
9h 47m
1 stop
Depart: Thu Jun 2 2016 Return: Tue Jun 7 2016 Trip spans 6 days
Southwest
Southwest
SJC
10:00a
MDW
2:10p
4h 10m
nonstop
MDW
3:40a
SJC
8:10a
4h 30m
nonstop
Depart: Fri Sep 30 2016 Return: Mon Oct 3 2016 Trip spans 4 days
Delta
Delta
SJC
8:36a
MDW
4:13p
7h 37m
1 stop
MDW
11:30a
SJC
7:49p
8h 19m
1 stop
Depart: Sat May 7 2016 Return: Tue May 17 2016 Trip spans 11 days
Southwest
Southwest
SJC
10:55a
MDW
5:50p
6h 55m
1 stop
MDW
1:30a
SJC
8:00a
6h 30m
1 stop
Depart: Mon May 9 2016 Return: Wed May 18 2016 Trip spans 10 days
Delta
Delta
SJC
6:28p
MDW
3:34a
9h 06m
1 stop
MDW
9:55a
SJC
7:48p
9h 53m
1 stop
Depart: Tue Sep 6 2016 Return: Tue Sep 13 2016 Trip spans 8 days
Southwest
Southwest
SJC
12:10p
MDW
5:55p
5h 45m
1 stop
MDW
1:40p
SJC
8:00p
6h 20m
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
829 1:35 pm 7:45 pm Apr 30 - Jun 4
2554 2:00 pm 8:10 pm May 1 - May 22
3293 2:00 pm 8:10 pm May 30 - May 30
3363 2:00 pm 8:10 pm May 31 - Jun 3
3363 2:00 pm 8:10 pm Apr 28 - May 27
1091 2:05 pm 8:10 pm Jun 6 - Jul 1
2165 2:05 pm 8:10 pm Jun 5 - Jun 26
3363 2:10 pm 8:20 pm May 29 - May 29
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

San Jose
$274
Destination

Chicago
$274