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
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: Tue Apr 18 2017 Return: Tue Apr 25 2017 Trip spans 8 days
Delta
Delta
MDW
11:10a
OAK
9:02p
9h 52m
2 stops
OAK
2:00a
MDW
1:16p
11h 16m
2 stops
Depart: Sat Jun 24 2017 Return: Tue Jul 4 2017 Trip spans 11 days
Southwest
Southwest
MDW
1:25p
OAK
6:00p
4h 35m
nonstop
OAK
1:55a
MDW
6:00a
4h 05m
nonstop
Depart: Mon Apr 24 2017 Return: Tue Apr 25 2017 Trip spans 2 days
Delta
Delta
MDW
11:10a
OAK
9:02p
9h 52m
2 stops
OAK
2:00a
MDW
1:16p
11h 16m
2 stops
Depart: Wed May 3 2017 Return: Tue May 9 2017 Trip spans 7 days
Delta
Delta
MDW
11:20a
OAK
8:36p
9h 16m
2 stops
OAK
1:50a
MDW
11:59a
10h 09m
2 stops
Depart: Fri Apr 28 2017 Return: Wed May 3 2017 Trip spans 6 days
Delta
Delta
MDW
5:10a
OAK
4:05p
10h 55m
2 stops
OAK
6:11a
MDW
4:10p
9h 59m
2 stops
Depart: Thu Apr 27 2017 Return: Tue May 2 2017 Trip spans 6 days
Delta
Delta
MDW
7:05a
OAK
4:05p
9h 00m
2 stops
OAK
2:00a
MDW
1:11p
11h 11m
2 stops
Depart: Fri May 5 2017 Return: Mon May 8 2017 Trip spans 4 days
Delta
Delta
MDW
8:15a
OAK
8:59p
12h 44m
2 stops
OAK
1:50a
MDW
1:11p
11h 21m
2 stops
Depart: Mon Jun 26 2017 Return: Tue Jul 4 2017 Trip spans 9 days
Southwest
Southwest
MDW
3:50p
OAK
8:25p
4h 35m
nonstop
OAK
1:55a
MDW
6:00a
4h 05m
nonstop
Depart: Tue Mar 28 2017 Return: Tue Apr 4 2017 Trip spans 8 days
Delta
Delta
MDW
9:48a
OAK
9:09p
11h 21m
2 stops
OAK
7:30a
MDW
4:11p
8h 41m
2 stops
Depart: Tue Apr 4 2017 Return: Tue Apr 11 2017 Trip spans 8 days
Delta
Delta
MDW
7:05a
OAK
4:05p
9h 00m
2 stops
OAK
6:16a
MDW
4:25p
10h 09m
2 stops
Depart: Tue Apr 11 2017 Return: Wed Apr 12 2017 Trip spans 2 days
Delta
Delta
MDW
7:05a
OAK
4:05p
9h 00m
2 stops
OAK
2:15a
MDW
10:52a
8h 37m
2 stops
Depart: Sun Apr 16 2017 Return: Tue Apr 25 2017 Trip spans 10 days
Delta
Delta
MDW
5:10a
OAK
7:15p
14h 05m
2 stops
OAK
2:00a
MDW
10:52a
8h 52m
2 stops
Depart: Thu May 18 2017 Return: Tue May 23 2017 Trip spans 6 days
Delta
Delta
MDW
8:15a
OAK
8:59p
12h 44m
2 stops
OAK
6:11a
MDW
4:10p
9h 59m
2 stops
Depart: Fri Apr 21 2017 Return: Mon Apr 24 2017 Trip spans 4 days
Delta
Delta
MDW
8:59a
OAK
9:02p
12h 03m
2 stops
OAK
2:15a
MDW
12:00p
9h 45m
2 stops
Depart: Mon Apr 3 2017 Return: Wed Apr 5 2017 Trip spans 3 days
Delta
Delta
MDW
11:10a
OAK
9:02p
9h 52m
2 stops
OAK
2:15a
MDW
12:00p
9h 45m
2 stops
Depart: Sat May 20 2017 Return: Tue May 23 2017 Trip spans 4 days
Delta
Delta
MDW
2:30a
OAK
12:15p
9h 45m
2 stops
OAK
6:11a
MDW
4:10p
9h 59m
2 stops
Depart: Mon Apr 10 2017 Return: Wed Apr 12 2017 Trip spans 3 days
Delta
Delta
MDW
5:10a
OAK
4:05p
10h 55m
2 stops
OAK
6:16a
MDW
4:11p
9h 55m
2 stops
Depart: Sat Apr 15 2017 Return: Sat Apr 22 2017 Trip spans 8 days
Delta
Delta
MDW
7:02a
OAK
7:15p
12h 13m
2 stops
OAK
2:15a
MDW
10:51a
8h 36m
2 stops
Depart: Mon Apr 17 2017 Return: Wed Apr 19 2017 Trip spans 3 days
Delta
Delta
MDW
8:59a
OAK
9:02p
12h 03m
2 stops
OAK
2:15a
MDW
10:11a
7h 56m
2 stops
Depart: Wed Apr 26 2017 Return: Mon May 1 2017 Trip spans 6 days
Delta
Delta
MDW
5:10a
OAK
4:39p
11h 29m
2 stops
OAK
2:15a
MDW
11:59a
9h 44m
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
338 8:30 am 11:05 am Apr 25 - Jun 2
4784 8:30 am 11:05 am Mar 20 - Apr 24
2627 8:40 am 11:15 am Mar 25 - Apr 22
425 9:05 am 11:35 am Mar 26 - Apr 23
2891 9:35 am 12:10 pm Apr 29 - Jun 3
222 3:45 pm 6:20 pm Apr 25 - May 26
4490 6:35 pm 9:10 pm Apr 29 - May 27
1875 7:40 pm 10:15 pm Apr 26 - Jun 2
1875 7:50 pm 10:25 pm Apr 25 - Apr 25
2215 7:55 pm 10:30 pm Mar 25 - Apr 22
2375 8:10 pm 10:45 pm Mar 20 - Apr 24
3689 8:35 pm 11:05 pm Mar 26 - Apr 23
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

Chicago
$262
Destination

Oakland
$262
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