Find Deals on 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
Students
under 26
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: Wed May 31 2017 Return: Sat Jun 3 2017 Trip spans 4 days
Delta
Delta
MDW
7:00a
OAK
3:50p
8h 50m
2 stops
OAK
8:35a
MDW
4:08p
7h 33m
1 stop
Depart: Sun Jan 29 2017 Return: Wed Feb 1 2017 Trip spans 4 days
Major Airline
Major Airline
MDW
1:00a
OAK
6:40a
5h 40m
1 stop
OAK
1:00a
MDW
2:40a
1h 40m
1 stop
Depart: Mon Jan 30 2017 Return: Tue Jan 31 2017 Trip spans 2 days
Delta
Delta
MDW
9:08a
OAK
8:02p
10h 54m
2 stops
OAK
12:35a
MDW
9:51a
9h 16m
2 stops
Depart: Tue Jan 31 2017 Return: Wed Feb 1 2017 Trip spans 2 days
Delta
Delta
MDW
4:15a
OAK
1:57p
9h 42m
2 stops
OAK
6:41a
MDW
3:09p
8h 28m
2 stops
Depart: Wed Feb 1 2017 Return: Thu Feb 2 2017 Trip spans 2 days
Delta
Delta
MDW
1:20a
OAK
10:43a
9h 23m
2 stops
OAK
5:00a
MDW
3:09p
10h 09m
2 stops
Depart: Thu Feb 2 2017 Return: Fri Feb 3 2017 Trip spans 2 days
Delta
Delta
MDW
7:35a
OAK
8:02p
12h 27m
2 stops
OAK
5:00a
MDW
3:46p
10h 46m
2 stops
Depart: Fri Feb 3 2017 Return: Tue Feb 7 2017 Trip spans 5 days
Delta
Delta
MDW
7:20a
OAK
8:02p
12h 42m
2 stops
OAK
12:35a
MDW
10:22a
9h 47m
2 stops
Depart: Tue Feb 7 2017 Return: Thu Feb 9 2017 Trip spans 3 days
Delta
Delta
MDW
10:29a
OAK
8:02p
9h 33m
2 stops
OAK
1:00a
MDW
9:51a
8h 51m
2 stops
Depart: Wed Feb 8 2017 Return: Mon Feb 13 2017 Trip spans 6 days
Delta
Delta
MDW
8:09a
OAK
8:02p
11h 53m
2 stops
OAK
12:32p
MDW
1:40a
13h 08m
2 stops
Depart: Mon Feb 13 2017 Return: Wed Feb 22 2017 Trip spans 10 days
Delta
Delta
MDW
7:35a
OAK
8:02p
12h 27m
2 stops
OAK
12:40p
MDW
1:39a
12h 59m
2 stops
Depart: Tue Feb 14 2017 Return: Wed Feb 22 2017 Trip spans 9 days
Delta
Delta
MDW
1:00a
OAK
1:57p
12h 57m
2 stops
OAK
12:40p
MDW
1:39a
12h 59m
2 stops
Depart: Tue Feb 28 2017 Return: Thu Mar 2 2017 Trip spans 3 days
Delta
Delta
MDW
1:20a
OAK
10:39a
9h 19m
2 stops
OAK
12:32a
MDW
3:00p
14h 28m
2 stops
Depart: Wed Apr 19 2017 Return: Sat Apr 22 2017 Trip spans 4 days
Delta
Delta
MDW
7:00a
OAK
8:00p
13h 00m
2 stops
OAK
2:03a
MDW
10:45a
8h 42m
2 stops
Depart: Thu Apr 20 2017 Return: Tue Apr 25 2017 Trip spans 6 days
Delta
Delta
MDW
7:00a
OAK
3:50p
8h 50m
2 stops
OAK
2:00a
MDW
10:46a
8h 46m
2 stops
Depart: Thu May 4 2017 Return: Wed May 10 2017 Trip spans 7 days
Delta
Delta
MDW
7:00a
OAK
3:50p
8h 50m
2 stops
OAK
2:00a
MDW
3:16p
13h 16m
2 stops
Depart: Tue May 9 2017 Return: Tue May 16 2017 Trip spans 8 days
Delta
Delta
MDW
7:00a
OAK
3:50p
8h 50m
2 stops
OAK
2:00a
MDW
1:03p
11h 03m
2 stops
Depart: Wed May 10 2017 Return: Tue May 16 2017 Trip spans 7 days
Delta
Delta
MDW
5:05a
OAK
3:50p
10h 45m
2 stops
OAK
2:00a
MDW
1:03p
11h 03m
2 stops
Depart: Thu May 11 2017 Return: Tue May 16 2017 Trip spans 6 days
Delta
Delta
MDW
5:05a
OAK
3:50p
10h 45m
2 stops
OAK
2:00a
MDW
1:03p
11h 03m
2 stops
Depart: Sat Feb 18 2017 Return: Wed Feb 22 2017 Trip spans 5 days
Delta
Delta
MDW
7:17a
OAK
6:56p
11h 39m
2 stops
OAK
12:40p
MDW
1:39a
12h 59m
2 stops
Depart: Tue Apr 11 2017 Return: Tue Apr 18 2017 Trip spans 8 days
Delta
Delta
MDW
5:05a
OAK
3:50p
10h 45m
2 stops
OAK
2:03a
MDW
11:58a
9h 55m
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
1889 8:40 am 11:25 am Feb 1 - Feb 7
1889 8:40 am 11:25 am Feb 21 - Mar 3
1889 8:40 am 11:25 am Feb 13 - Feb 20
1889 8:40 am 11:25 am Feb 14 - Feb 14
1889 8:40 am 11:25 am Feb 8 - Feb 10
1889 8:40 am 11:25 am Jan 30 - Jan 31
2503 8:45 am 11:30 am Jan 21 - Mar 4
2739 9:05 am 11:50 am Feb 19 - Mar 5
2739 9:05 am 11:50 am Feb 12 - Feb 12
5801 9:05 am 11:50 am Feb 5 - Feb 5
4532 7:45 pm 10:30 pm Jan 23 - Feb 13
4532 7:45 pm 10:30 pm Feb 15 - Mar 8
4209 8:15 pm 10:55 pm Feb 12 - Mar 5
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

Chicago
$268
Destination

Oakland
$268
Airlines