Find Deals on Flights from Oakland to Chicago Midway (OAK - 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 Oakland to Chicago Midway

(Round-trip)
Depart: Wed Apr 12 2017 Return: Tue Apr 18 2017 Trip spans 7 days
Delta
Delta
OAK
2:15a
MDW
12:00p
9h 45m
2 stops
MDW
7:05a
OAK
4:05p
9h 00m
2 stops
Depart: Thu Aug 10 2017 Return: Mon Aug 14 2017 Trip spans 5 days
Southwest
Southwest
OAK
3:30a
MDW
7:30a
4h 00m
nonstop
MDW
3:50p
OAK
8:25p
4h 35m
nonstop
Depart: Wed Apr 19 2017 Return: Sat Apr 29 2017 Trip spans 11 days
Delta
Delta
OAK
2:00a
MDW
4:11p
14h 11m
2 stops
MDW
7:02a
OAK
7:15p
12h 13m
2 stops
Depart: Fri Mar 31 2017 Return: Mon Apr 3 2017 Trip spans 4 days
Major Airline
Major Airline
OAK
2:00a
MDW
3:40a
1h 40m
1 stop
MDW
2:00a
OAK
7:40a
5h 40m
1 stop
Depart: Tue May 2 2017 Return: Fri May 5 2017 Trip spans 4 days
Delta
Delta
OAK
2:00a
MDW
11:59a
9h 59m
2 stops
MDW
9:00a
OAK
8:59p
11h 59m
2 stops
Depart: Sat May 6 2017 Return: Tue May 9 2017 Trip spans 4 days
Delta
Delta
OAK
7:30a
MDW
4:07p
8h 37m
2 stops
MDW
11:20a
OAK
8:59p
9h 39m
2 stops
Depart: Wed Apr 26 2017 Return: Thu Apr 27 2017 Trip spans 2 days
Delta
Delta
OAK
2:15a
MDW
12:00p
9h 45m
2 stops
MDW
7:05a
OAK
4:05p
9h 00m
2 stops
Depart: Thu May 4 2017 Return: Tue May 9 2017 Trip spans 6 days
Delta
Delta
OAK
6:11a
MDW
4:10p
9h 59m
2 stops
MDW
8:15a
OAK
8:59p
12h 44m
2 stops
Depart: Sat May 20 2017 Return: Tue May 23 2017 Trip spans 4 days
Delta
Delta
OAK
7:30a
MDW
4:07p
8h 37m
2 stops
MDW
8:15a
OAK
8:59p
12h 44m
2 stops
Depart: Mon Apr 10 2017 Return: Wed Apr 12 2017 Trip spans 3 days
Delta
Delta
OAK
2:50p
MDW
3:37a
12h 47m
2 stops
MDW
8:24a
OAK
9:02p
12h 38m
2 stops
Depart: Thu Apr 13 2017 Return: Tue Apr 18 2017 Trip spans 6 days
Delta
Delta
OAK
2:15a
MDW
12:00p
9h 45m
2 stops
MDW
7:05a
OAK
4:05p
9h 00m
2 stops
Depart: Mon Apr 24 2017 Return: Thu Apr 27 2017 Trip spans 4 days
Delta
Delta
OAK
2:15a
MDW
10:11a
7h 56m
2 stops
MDW
5:10a
OAK
4:05p
10h 55m
2 stops
Depart: Fri Apr 28 2017 Return: Mon May 1 2017 Trip spans 4 days
Delta
Delta
OAK
2:50p
MDW
2:47a
11h 57m
2 stops
MDW
11:20a
OAK
8:59p
9h 39m
2 stops
Depart: Wed May 3 2017 Return: Mon May 8 2017 Trip spans 6 days
Delta
Delta
OAK
6:11a
MDW
4:10p
9h 59m
2 stops
MDW
11:20a
OAK
8:59p
9h 39m
2 stops
Depart: Tue Apr 18 2017 Return: Fri Apr 21 2017 Trip spans 4 days
Delta
Delta
OAK
7:30a
MDW
4:11p
8h 41m
2 stops
MDW
8:29a
OAK
9:02p
12h 33m
2 stops
Depart: Thu Apr 27 2017 Return: Tue May 2 2017 Trip spans 6 days
Delta
Delta
OAK
6:16a
MDW
4:11p
9h 55m
2 stops
MDW
5:10a
OAK
4:19p
11h 09m
2 stops
Depart: Tue May 9 2017 Return: Fri May 12 2017 Trip spans 4 days
Delta
Delta
OAK
6:11a
MDW
4:10p
9h 59m
2 stops
MDW
2:30a
OAK
12:20p
9h 50m
2 stops
Depart: Tue Mar 28 2017 Return: Thu Mar 30 2017 Trip spans 3 days
Delta
Delta
OAK
2:15a
MDW
12:10p
9h 55m
2 stops
MDW
3:15a
OAK
2:22p
11h 07m
2 stops
Depart: Wed Mar 29 2017 Return: Sat Apr 1 2017 Trip spans 4 days
Delta
Delta
OAK
7:37a
MDW
4:11p
8h 34m
2 stops
MDW
2:25a
OAK
2:19p
11h 54m
2 stops
Depart: Tue Sep 19 2017 Return: Mon Sep 25 2017 Trip spans 7 days
Delta
Delta
OAK
2:00a
MDW
1:03p
11h 03m
2 stops
MDW
11:24a
OAK
8:35p
9h 11m
2 stops
Select an airline:  Southwest
Direct flights OAK to MDW on Southwest
Flight # Depart OAK Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
1193 6:25 am 12:35 pm Mar 27 - Apr 24
1289 6:25 am 12:35 pm Apr 25 - Jun 2
6346 6:40 am 12:45 pm Apr 1 - Apr 22
4476 6:55 am 1:00 pm Apr 29 - Jun 3
4597 7:00 am 1:10 pm Apr 30 - May 28
3935 7:20 am 1:25 pm Apr 2 - Apr 23
1592 8:55 am 3:00 pm Apr 25 - May 8
4596 9:05 am 3:10 pm Apr 30 - May 28
2631 1:55 pm 8:00 pm Apr 29 - Apr 29
2515 2:25 pm 8:30 pm Apr 30 - May 28
594 2:40 pm 8:45 pm Apr 25 - Apr 25
594 2:40 pm 8:45 pm Apr 26 - May 26
1443 2:50 pm 8:55 pm Mar 27 - Apr 24
4826 2:55 pm 9:00 pm Apr 1 - Apr 22
5771 3:10 pm 9:15 pm Apr 2 - Apr 23
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

Oakland
$294
Destination

Chicago
$294
Airlines Airline reviews

4 travelers who booked a flight from Oakland to Chicago rated their chosen airlines with an average of 7.6.

Overall
7.5
Boarding
8.0
Crew
8.0
Comfort
7.5
Food
5.5
Entertainment
7.5