Find Cheap Flights from Chicago Midway to Oakland (MDW - OAK)

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 Chicago Midway to Oakland

(Round-trip)
Depart: Thu Sep 28 2017 Return: Mon Oct 2 2017 Trip spans 5 days
Delta
Delta
MDW
2:30a
OAK
11:55a
9h 25m
2 stops
OAK
2:00a
MDW
10:49a
8h 49m
2 stops
Depart: Tue Jul 18 2017 Return: Mon Jul 24 2017 Trip spans 7 days
Southwest
Southwest
MDW
3:50p
OAK
8:25p
4h 35m
nonstop
OAK
3:30a
MDW
7:30a
4h 00m
nonstop
Depart: Sat Sep 30 2017 Return: Tue Oct 3 2017 Trip spans 4 days
Delta
Delta
MDW
2:00a
OAK
11:55a
9h 55m
2 stops
OAK
2:00a
MDW
1:03p
11h 03m
2 stops
Depart: Sat Jul 8 2017 Return: Tue Jul 11 2017 Trip spans 4 days
Delta
Delta
MDW
8:55a
OAK
8:50p
11h 55m
2 stops
OAK
2:15a
MDW
12:09p
9h 54m
2 stops
Depart: Fri Sep 8 2017 Return: Tue Sep 12 2017 Trip spans 5 days
Delta
Delta
MDW
2:30a
OAK
3:50p
13h 20m
2 stops
OAK
2:00a
MDW
1:03p
11h 03m
2 stops
Depart: Fri Sep 29 2017 Return: Tue Oct 3 2017 Trip spans 5 days
Delta
Delta
MDW
2:30a
OAK
11:55a
9h 25m
2 stops
OAK
2:00a
MDW
1:03p
11h 03m
2 stops
Depart: Thu Sep 7 2017 Return: Sat Sep 16 2017 Trip spans 10 days
Delta
Delta
MDW
8:20a
OAK
8:35p
12h 15m
2 stops
OAK
2:00a
MDW
10:44a
8h 44m
2 stops
Depart: Tue Sep 12 2017 Return: Sat Sep 16 2017 Trip spans 5 days
Delta
Delta
MDW
5:08a
OAK
3:50p
10h 42m
2 stops
OAK
2:00a
MDW
10:44a
8h 44m
2 stops
Depart: Thu Oct 5 2017 Return: Sun Oct 15 2017 Trip spans 11 days
Delta
Delta
MDW
5:08a
OAK
3:50p
10h 42m
2 stops
OAK
2:00a
MDW
10:49a
8h 49m
2 stops
Depart: Thu Jul 6 2017 Return: Tue Jul 11 2017 Trip spans 6 days
Delta
Delta
MDW
11:46a
OAK
7:48p
8h 02m
1 stop
OAK
2:15a
MDW
12:09p
9h 54m
2 stops
Depart: Wed Oct 11 2017 Return: Sun Oct 15 2017 Trip spans 5 days
Delta
Delta
MDW
2:30a
OAK
3:50p
13h 20m
2 stops
OAK
2:00a
MDW
10:49a
8h 49m
2 stops
Depart: Sat Sep 2 2017 Return: Wed Sep 6 2017 Trip spans 5 days
Delta
Delta
MDW
2:30a
OAK
3:50p
13h 20m
2 stops
OAK
2:00a
MDW
1:03p
11h 03m
2 stops
Depart: Fri Nov 3 2017 Return: Tue Nov 7 2017 Trip spans 5 days
Delta
Delta
MDW
2:30a
OAK
2:07p
11h 37m
2 stops
OAK
1:00a
MDW
1:12p
12h 12m
2 stops
Depart: Wed Aug 23 2017 Return: Wed Aug 30 2017 Trip spans 8 days
Delta
Delta
MDW
5:07a
OAK
4:19p
11h 12m
2 stops
OAK
6:30a
MDW
5:07p
10h 37m
2 stops
Depart: Sat Aug 26 2017 Return: Sat Sep 2 2017 Trip spans 8 days
Delta
Delta
MDW
2:30a
OAK
11:55a
9h 25m
2 stops
OAK
2:45p
MDW
3:36a
12h 51m
2 stops
Depart: Fri Jul 7 2017 Return: Tue Jul 11 2017 Trip spans 5 days
Delta
Delta
MDW
11:46a
OAK
7:48p
8h 02m
1 stop
OAK
2:15a
MDW
12:09p
9h 54m
2 stops
Depart: Thu Aug 24 2017 Return: Tue Aug 29 2017 Trip spans 6 days
Delta
Delta
MDW
5:07a
OAK
4:19p
11h 12m
2 stops
OAK
2:00a
MDW
1:03p
11h 03m
2 stops
Depart: Mon Jul 3 2017 Return: Sat Jul 8 2017 Trip spans 6 days
Delta
Delta
MDW
8:10a
OAK
7:35p
11h 25m
2 stops
OAK
2:00a
MDW
10:43a
8h 43m
2 stops
Depart: Sat Jul 1 2017 Return: Sun Jul 2 2017 Trip spans 2 days
Delta
Delta
MDW
8:55a
OAK
8:50p
11h 55m
2 stops
OAK
2:15a
MDW
4:18p
14h 03m
2 stops
Depart: Tue Jul 11 2017 Return: Tue Jul 18 2017 Trip spans 8 days
Delta
Delta
MDW
12:45p
OAK
9:22p
8h 37m
2 stops
OAK
2:15a
MDW
1:12p
10h 57m
2 stops
Select an airline:  Southwest
Direct flights MDW to OAK on Southwest
Flight # Depart MDW Arrive OAK Sun Mon Tue Wed Thu Fri Sat Valid Between
1349 8:10 am 10:45 am Jun 21 - Jun 30
1349 8:10 am 10:45 am Jul 4 - Aug 14
1794 8:55 am 11:30 am Jun 25 - Aug 13
5978 9:40 am 12:10 pm Jun 24 - Aug 12
403 12:05 pm 2:40 pm Jun 21 - Aug 14
3757 12:35 pm 3:10 pm Jun 25 - Aug 13
4454 1:50 pm 4:30 pm Jun 24 - Aug 12
3733 4:20 pm 6:55 pm Jul 3 - Jul 3
4234 5:25 pm 8:00 pm Jul 8 - Aug 12
4234 5:25 pm 8:00 pm Jun 24 - Jul 1
411 5:40 pm 8:15 pm Jul 5 - Aug 14
411 5:40 pm 8:15 pm Jun 21 - Jun 30
3957 5:50 pm 8:25 pm Jul 4 - Jul 4
5430 5:55 pm 8:30 pm Jun 25 - Aug 13
1010 7:50 pm 10:25 pm Jun 21 - Aug 14
5345 7:55 pm 10:30 pm Jul 8 - Aug 12
1369 8:20 pm 10:55 pm Jul 2 - Aug 13
6114 8:50 pm 11:25 pm Jul 1 - Jul 1
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

Chicago
$272
Destination

Oakland
$272
Airlines Airline reviews

1 traveler who booked a flight from Chicago to Oakland rated their chosen airline with an average of 10.0

Overall
10.0
Boarding
10.0
Crew
10.0
Comfort
10.0
Food
10.0
Entertainment
10.0