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Find Flight Deals 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 Apr 14 2015 Return: Wed Apr 15 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
11:45a
OAK
4:30p
4h 45m
nonstop
OAK
4:50a
ORD
8:55a
4h 05m
nonstop
Depart: Wed Apr 15 2015 Return: Tue Apr 21 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
11:45a
OAK
4:30p
4h 45m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Tue Apr 21 2015 Return: Wed Apr 22 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:20p
4h 35m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Wed Apr 22 2015 Return: Wed Apr 29 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:20p
4h 35m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Tue Apr 28 2015 Return: Tue May 5 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:20p
4h 35m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Wed Apr 29 2015 Return: Tue May 5 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:20p
4h 35m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Tue May 5 2015 Return: Tue May 12 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:20p
4h 35m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Wed May 6 2015 Return: Tue May 12 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:20p
4h 35m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Tue May 12 2015 Return: Wed May 13 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:20p
4h 35m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Wed May 13 2015 Return: Tue May 19 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:20p
4h 35m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Thu Apr 9 2015 Return: Tue Apr 14 2015 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
11:45a
OAK
4:30p
4h 45m
nonstop
OAK
4:50a
ORD
8:55a
4h 05m
nonstop
Depart: Fri Apr 10 2015 Return: Tue Apr 14 2015 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
11:45a
OAK
4:30p
4h 45m
nonstop
OAK
4:50a
ORD
8:55a
4h 05m
nonstop
Depart: Sat Apr 11 2015 Return: Wed Apr 15 2015 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
11:45a
OAK
4:30p
4h 45m
nonstop
OAK
4:50a
ORD
8:55a
4h 05m
nonstop
Depart: Mon Apr 13 2015 Return: Tue Apr 14 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
11:45a
OAK
4:30p
4h 45m
nonstop
OAK
4:50a
ORD
8:55a
4h 05m
nonstop
Depart: Thu Apr 16 2015 Return: Tue Apr 21 2015 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:20p
4h 35m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Sat Apr 18 2015 Return: Tue Apr 21 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:20p
4h 35m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Mon Apr 20 2015 Return: Tue Apr 21 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:20p
4h 35m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Thu Apr 23 2015 Return: Wed Apr 29 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:20p
4h 35m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Sun May 3 2015 Return: Mon May 4 2015 Trip spans 2 days
American Airlines
American Airlines
ORD
1:00a
OAK
7:22a
6h 22m
1 stop
OAK
8:27a
ORD
2:46p
6h 19m
1 stop
Depart: Sun Aug 16 2015 Return: Tue Aug 18 2015 Trip spans 3 days
Delta
Delta
MDW
9:50a
OAK
7:35p
9h 45m
1 stop
OAK
6:30a
MDW
2:53p
8h 23m
2 stops
Direct flights CHI to OAK on Southwest
Flight # Depart MDW Arrive OAK Sun Mon Tue Wed Thu Fri Sat Valid Between
4985 8:30 am 11:10 am Apr 8 - Apr 17
4985 8:30 am 11:10 am Apr 19 - Apr 24
4985 8:30 am 11:10 am Apr 26 - May 22
1006 8:40 am 11:30 am Apr 7 - Apr 7
156 8:40 am 11:30 am Mar 26 - Apr 6
1145 8:55 am 11:40 am Mar 28 - Apr 4
2636 8:55 am 11:35 am Apr 11 - May 2
524 4:45 pm 7:25 pm Apr 8 - Apr 17
524 4:45 pm 7:25 pm Apr 19 - Apr 24
524 4:45 pm 7:25 pm Apr 26 - May 10
2544 5:30 pm 8:10 pm Mar 28 - Apr 4
1998 6:35 pm 9:10 pm Apr 11 - May 16
2409 7:15 pm 10:00 pm Apr 5 - Apr 6
3475 7:15 pm 10:00 pm Apr 7 - Apr 7
555 7:40 pm 10:20 pm Apr 8 - May 22
Airports
Origin

Chicago
only $187
only $480
Destination

Oakland
$187