Find Cheap 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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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: Mon Oct 30 2017 Return: Sat Dec 16 2017 Trip spans 48 days
Major Airline
Major Airline
SJC
2:00a
MDW
3:39a
1h 39m
nonstop
MDW
1:00a
SJC
6:39a
5h 39m
nonstop
Depart: Tue Sep 12 2017 Return: Thu Sep 14 2017 Trip spans 3 days
Southwest
Southwest
SJC
10:35a
MDW
2:40p
4h 05m
nonstop
MDW
3:45p
SJC
8:20p
4h 35m
nonstop
Depart: Wed Sep 13 2017 Return: Sat Sep 16 2017 Trip spans 4 days
Delta
Delta
SJC
2:15a
MDW
8:49a
6h 34m
1 stop
MDW
1:10p
SJC
7:35p
6h 25m
1 stop
Depart: Sat Sep 16 2017 Return: Tue Sep 19 2017 Trip spans 4 days
Delta
Delta
SJC
8:45a
MDW
5:05p
8h 20m
1 stop
MDW
2:00a
SJC
9:53a
7h 53m
1 stop
Depart: Sat Oct 7 2017 Return: Tue Oct 10 2017 Trip spans 4 days
Major Airline
Major Airline
SJC
1:00a
MDW
2:39a
1h 39m
1 stop
MDW
1:00a
SJC
6:39a
5h 39m
1 stop
Depart: Tue Sep 26 2017 Return: Wed Oct 4 2017 Trip spans 9 days
Delta
Delta
SJC
10:00a
MDW
4:15p
6h 15m
1 stop
MDW
2:00a
SJC
9:53a
7h 53m
1 stop
Depart: Sat Jul 8 2017 Return: Tue Jul 11 2017 Trip spans 4 days
Major Airline
Major Airline
SJC
1:00a
MDW
2:39a
1h 39m
nonstop
MDW
1:00a
SJC
6:39a
5h 39m
nonstop
Depart: Tue Oct 10 2017 Return: Sat Oct 14 2017 Trip spans 5 days
Delta
Delta
SJC
2:30a
MDW
8:49a
6h 19m
1 stop
MDW
1:10p
SJC
7:28p
6h 18m
1 stop
Depart: Wed Oct 11 2017 Return: Sat Oct 14 2017 Trip spans 4 days
Delta
Delta
SJC
10:00a
MDW
4:15p
6h 15m
1 stop
MDW
11:24a
SJC
7:28p
8h 04m
1 stop
Depart: Sat Nov 4 2017 Return: Tue Nov 7 2017 Trip spans 4 days
Delta
Delta
SJC
8:45a
MDW
5:05p
8h 20m
1 stop
MDW
9:05a
SJC
6:13p
9h 08m
1 stop
Depart: Fri Sep 15 2017 Return: Mon Sep 18 2017 Trip spans 4 days
Major Airline
Major Airline
SJC
2:00a
MDW
3:39a
1h 39m
nonstop
MDW
2:00a
SJC
7:39a
5h 39m
nonstop
Depart: Sat Aug 19 2017 Return: Wed Aug 23 2017 Trip spans 5 days
Delta
Delta
SJC
2:25a
MDW
10:45a
8h 20m
1 stop
MDW
2:30a
SJC
11:16a
8h 46m
1 stop
Depart: Wed Aug 23 2017 Return: Fri Aug 25 2017 Trip spans 3 days
Delta
Delta
SJC
7:18a
MDW
4:18p
9h 00m
1 stop
MDW
6:10a
SJC
3:35p
9h 25m
1 stop
Depart: Mon Jul 10 2017 Return: Wed Jul 12 2017 Trip spans 3 days
Major Airline
Major Airline
SJC
2:00a
MDW
3:39a
1h 39m
nonstop
MDW
2:00a
SJC
7:39a
5h 39m
nonstop
Depart: Sat Aug 26 2017 Return: Tue Aug 29 2017 Trip spans 4 days
Delta
Delta
SJC
2:15a
MDW
10:44a
8h 29m
1 stop
MDW
1:10p
SJC
7:35p
6h 25m
1 stop
Depart: Sat Sep 2 2017 Return: Wed Sep 6 2017 Trip spans 5 days
Delta
Delta
SJC
8:45a
MDW
4:51p
8h 06m
1 stop
MDW
2:30a
SJC
9:03a
6h 33m
1 stop
Depart: Mon Jul 31 2017 Return: Tue Aug 1 2017 Trip spans 2 days
Major Airline
Major Airline
SJC
1:00a
MDW
2:39a
1h 39m
nonstop
MDW
1:00a
SJC
6:39a
5h 39m
nonstop
Depart: Sun Sep 3 2017 Return: Wed Sep 6 2017 Trip spans 4 days
Delta
Delta
SJC
2:15a
MDW
10:49a
8h 34m
1 stop
MDW
2:30a
SJC
9:03a
6h 33m
1 stop
Depart: Wed Sep 27 2017 Return: Fri Sep 29 2017 Trip spans 3 days
Delta
Delta
SJC
6:25p
MDW
3:36a
9h 11m
1 stop
MDW
5:08a
SJC
11:28a
6h 20m
1 stop
Depart: Thu Aug 3 2017 Return: Sun Aug 13 2017 Trip spans 11 days
Major Airline
Major Airline
SJC
1:00a
MDW
2:39a
1h 39m
nonstop
MDW
1:00a
SJC
6:39a
5h 39m
nonstop
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
4450 6:30 am 12:35 pm Jul 4 - Jul 4
554 6:30 am 12:35 pm Jul 3 - Jul 3
554 6:30 am 12:35 pm Jun 21 - Jun 30
554 6:30 am 12:35 pm Jul 5 - Aug 14
4953 6:35 am 12:40 pm Jun 25 - Aug 13
2417 7:00 am 1:05 pm Jun 24 - Aug 12
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

San Jose
$227
Destination

Chicago
$227
Airlines Airline reviews

6 travelers who booked a flight from San Jose to Chicago rated their chosen airlines with an average of 9.0.

Overall
9.3
Boarding
9.3
Crew
9.3
Comfort
9.3
Food
8.7
Entertainment
8.3