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Find Deals on Flights from Chicago to Oakland (CHI - OAK)

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago to Oakland

(Round-trip)
Depart: Tue Aug 25 2015 Return: Wed Aug 26 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:17p
4h 32m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Wed Aug 26 2015 Return: Tue Sep 1 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:17p
4h 32m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Sat Aug 29 2015 Return: Tue Sep 1 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:17p
4h 32m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Tue Sep 1 2015 Return: Wed Sep 9 2015 Trip spans 9 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:17p
4h 32m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Wed Sep 2 2015 Return: Wed Sep 9 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:17p
4h 32m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Wed Sep 9 2015 Return: Wed Sep 16 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:17p
4h 32m
nonstop
OAK
4:29a
ORD
8:33a
4h 04m
nonstop
Depart: Tue Sep 15 2015 Return: Tue Sep 22 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
11:30a
OAK
4:01p
4h 31m
nonstop
OAK
4:29a
ORD
8:33a
4h 04m
nonstop
Depart: Wed Sep 16 2015 Return: Tue Sep 22 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
11:30a
OAK
4:01p
4h 31m
nonstop
OAK
4:29a
ORD
8:33a
4h 04m
nonstop
Depart: Tue Sep 22 2015 Return: Sat Sep 26 2015 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
11:30a
OAK
4:01p
4h 31m
nonstop
OAK
4:29a
ORD
8:33a
4h 04m
nonstop
Depart: Wed Sep 23 2015 Return: Sat Sep 26 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
11:30a
OAK
4:01p
4h 31m
nonstop
OAK
4:29a
ORD
8:33a
4h 04m
nonstop
Depart: Sat Sep 26 2015 Return: Tue Sep 29 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
11:30a
OAK
4:01p
4h 31m
nonstop
OAK
4:29a
ORD
8:33a
4h 04m
nonstop
Depart: Wed Sep 30 2015 Return: Wed Oct 7 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
11:30a
OAK
4:01p
4h 31m
nonstop
OAK
4:29a
ORD
8:33a
4h 04m
nonstop
Depart: Sat Oct 3 2015 Return: Tue Oct 6 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
11:30a
OAK
4:01p
4h 31m
nonstop
OAK
4:29a
ORD
8:33a
4h 04m
nonstop
Depart: Wed Oct 7 2015 Return: Sat Oct 10 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
11:30a
OAK
4:01p
4h 31m
nonstop
OAK
4:29a
ORD
8:33a
4h 04m
nonstop
Depart: Wed Oct 14 2015 Return: Wed Oct 21 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
11:30a
OAK
4:01p
4h 31m
nonstop
OAK
4:29a
ORD
8:33a
4h 04m
nonstop
Depart: Wed Oct 21 2015 Return: Wed Oct 28 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
11:30a
OAK
4:01p
4h 31m
nonstop
OAK
4:29a
ORD
8:33a
4h 04m
nonstop
Depart: Fri Jan 8 2016 Return: Mon Jan 11 2016 Trip spans 4 days
American Airlines
American Airlines
ORD
12:00a
OAK
6:15a
6h 15m
1 stop
OAK
2:15p
ORD
8:08p
5h 53m
1 stop
Depart: Fri Sep 4 2015 Return: Tue Sep 8 2015 Trip spans 5 days
Delta
Delta
MDW
2:30a
OAK
8:48a
6h 18m
1 stop
OAK
12:45p
MDW
6:06p
5h 21m
1 stop
Depart: Thu Jan 7 2016 Return: Tue Jan 12 2016 Trip spans 6 days
Delta
Delta
ORD
11:40a
OAK
7:47p
8h 07m
1 stop
OAK
1:05a
ORD
8:04a
6h 59m
1 stop
Depart: Wed Dec 23 2015 Return: Sun Dec 27 2015 Trip spans 5 days
US Airways
US Airways
ORD
12:00a
OAK
6:15a
6h 15m
1 stop
OAK
2:15p
ORD
8:08p
5h 53m
1 stop
Direct flights CHI to OAK on Southwest
Flight # Depart MDW Arrive OAK Sun Mon Tue Wed Thu Fri Sat Valid Between
527 8:10 am 10:45 am Jul 10 - Aug 7
30 8:30 am 11:10 am Jul 11 - Aug 8
1315 8:35 am 11:15 am Aug 9 - Sep 4
3331 12:15 pm 2:50 pm Jun 28 - Aug 7
1757 12:50 pm 3:30 pm Aug 9 - Aug 30
493 12:50 pm 3:30 pm Aug 10 - Aug 28
4361 3:45 pm 6:20 pm Jul 11 - Aug 8
1071 4:05 pm 6:45 pm Aug 10 - Sep 25
2913 4:10 pm 6:50 pm Aug 9 - Aug 30
3074 5:30 pm 8:05 pm Jul 11 - Aug 8
248 6:20 pm 8:55 pm Jul 10 - Aug 7
1862 7:05 pm 9:40 pm Jul 11 - Aug 8
2489 7:40 pm 10:20 pm Aug 9 - Oct 30
2342 8:05 pm 10:45 pm Jun 28 - Aug 7
Airports
Origin

Chicago
only $197
only $294
Destination

Oakland
$197