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: Sat Oct 22 2016 Return: Tue Oct 25 2016 Trip spans 4 days
Southwest
Southwest
SJC
3:00a
MDW
9:55a
6h 55m
1 stop
MDW
3:50p
SJC
8:30p
4h 40m
nonstop
Depart: Tue Oct 11 2016 Return: Wed Oct 19 2016 Trip spans 9 days
Delta
Delta
SJC
2:25a
MDW
10:49a
8h 24m
1 stop
MDW
9:59a
SJC
7:10p
9h 11m
1 stop
Depart: Wed Nov 2 2016 Return: Tue Nov 8 2016 Trip spans 7 days
Major Airline
Major Airline
SJC
4:40a
MDW
8:50a
4h 10m
nonstop
MDW
3:20a
SJC
8:05a
4h 45m
nonstop
Depart: Sat Oct 15 2016 Return: Wed Oct 19 2016 Trip spans 5 days
Delta
Delta
SJC
2:25a
MDW
8:45a
6h 20m
1 stop
MDW
8:30a
SJC
7:10p
10h 40m
1 stop
Depart: Tue Nov 1 2016 Return: Wed Nov 2 2016 Trip spans 2 days
Southwest
Southwest
SJC
4:40a
MDW
8:50a
4h 10m
nonstop
MDW
3:50p
SJC
8:30p
4h 40m
nonstop
Depart: Tue Nov 8 2016 Return: Wed Nov 9 2016 Trip spans 2 days
Major Airline
Major Airline
SJC
9:40a
MDW
1:45p
4h 05m
nonstop
MDW
3:20a
SJC
8:05a
4h 45m
nonstop
Depart: Tue Oct 18 2016 Return: Tue Oct 25 2016 Trip spans 8 days
Delta
Delta
SJC
2:25a
MDW
10:49a
8h 24m
1 stop
MDW
2:30a
SJC
9:26a
6h 56m
1 stop
Depart: Wed Nov 30 2016 Return: Wed Dec 7 2016 Trip spans 8 days
Major Airline
Major Airline
SJC
9:40a
MDW
1:45p
4h 05m
nonstop
MDW
3:20a
SJC
8:05a
4h 45m
nonstop
Depart: Tue Oct 25 2016 Return: Tue Nov 1 2016 Trip spans 8 days
Delta
Delta
SJC
2:25a
MDW
10:49a
8h 24m
1 stop
MDW
11:20a
SJC
6:02p
6h 42m
1 stop
Depart: Wed Jan 11 2017 Return: Sat Jan 14 2017 Trip spans 4 days
Major Airline
Major Airline
SJC
9:45a
MDW
1:50p
4h 05m
nonstop
MDW
3:50a
SJC
8:30a
4h 40m
nonstop
Depart: Wed Oct 26 2016 Return: Tue Nov 1 2016 Trip spans 7 days
Delta
Delta
SJC
8:28a
MDW
4:55p
8h 27m
1 stop
MDW
2:00a
SJC
9:48a
7h 48m
1 stop
Depart: Tue Jan 17 2017 Return: Tue Jan 24 2017 Trip spans 8 days
Major Airline
Major Airline
SJC
9:45a
MDW
1:50p
4h 05m
nonstop
MDW
4:05a
SJC
8:50a
4h 45m
nonstop
Depart: Sat Oct 29 2016 Return: Tue Nov 1 2016 Trip spans 4 days
Delta
Delta
SJC
2:25a
MDW
8:45a
6h 20m
1 stop
MDW
11:20a
SJC
6:02p
6h 42m
1 stop
Depart: Wed Oct 19 2016 Return: Tue Oct 25 2016 Trip spans 7 days
Major Airline
Major Airline
SJC
3:00a
MDW
10:15a
7h 15m
nonstop
MDW
3:50p
SJC
8:30p
4h 40m
nonstop
Depart: Sat Nov 5 2016 Return: Tue Nov 8 2016 Trip spans 4 days
Delta
Delta
SJC
2:25a
MDW
10:48a
8h 23m
1 stop
MDW
1:00a
SJC
8:56a
7h 56m
1 stop
Depart: Sat Nov 12 2016 Return: Tue Nov 15 2016 Trip spans 4 days
Major Airline
Major Airline
SJC
7:10a
MDW
12:35p
5h 25m
nonstop
MDW
3:20a
SJC
8:05a
4h 45m
nonstop
Depart: Thu Nov 24 2016 Return: Sat Nov 26 2016 Trip spans 3 days
Southwest
Southwest
SJC
8:35a
MDW
12:40p
4h 05m
nonstop
MDW
3:50a
SJC
8:40a
4h 50m
nonstop
Depart: Wed Nov 9 2016 Return: Wed Nov 16 2016 Trip spans 8 days
Delta
Delta
SJC
7:55a
MDW
2:56p
7h 01m
1 stop
MDW
1:30a
SJC
8:26a
6h 56m
1 stop
Depart: Sat Dec 3 2016 Return: Tue Dec 6 2016 Trip spans 4 days
Major Airline
Major Airline
SJC
7:10a
MDW
12:35p
5h 25m
nonstop
MDW
3:20a
SJC
8:05a
4h 45m
nonstop
Depart: Tue Feb 7 2017 Return: Tue Feb 14 2017 Trip spans 8 days
Delta
Delta
SJC
7:36a
MDW
3:13p
7h 37m
1 stop
MDW
1:00a
SJC
8:54a
7h 54m
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
3698 6:30 am 12:45 pm Oct 8 - Oct 29
2622 8:40 am 2:50 pm Oct 2 - Oct 30
2622 8:40 am 2:50 pm Oct 3 - Nov 4
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

San Jose
$263
Destination

Chicago
$263
Airlines Airline reviews

5 travelers who booked a flight from San Jose to Chicago rated their chosen airlines with an average of 8.8.

Overall
9.2
Boarding
9.2
Crew
9.2
Comfort
9.2
Food
8.4
Entertainment
8.0