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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: 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: Thu May 7 2015 Return: Tue May 12 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: Fri May 8 2015 Return: Tue May 12 2015 Trip spans 5 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 May 9 2015 Return: Tue May 12 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: Thu May 14 2015 Return: Sat May 16 2015 Trip spans 3 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 Jun 2 2015 Return: Tue Jun 9 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 Aug 19 2015 Return: Tue Aug 25 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: Tue Aug 25 2015 Return: Tue Sep 1 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 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: Tue Sep 22 2015 Return: Tue Sep 29 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
11:30a
OAK
4:01p
4h 31m
nonstop
OAK
4:30a
ORD
8:33a
4h 03m
nonstop
Depart: Wed Sep 23 2015 Return: Tue Sep 29 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
11:30a
OAK
4:01p
4h 31m
nonstop
OAK
4:30a
ORD
8:33a
4h 03m
nonstop
Depart: Tue Sep 29 2015 Return: Wed Sep 30 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
11:30a
OAK
4:01p
4h 31m
nonstop
OAK
4:30a
ORD
8:33a
4h 03m
nonstop
Depart: Wed Sep 30 2015 Return: Tue Oct 6 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
11:30a
OAK
4:01p
4h 31m
nonstop
OAK
4:30a
ORD
8:33a
4h 03m
nonstop
Depart: Wed Oct 7 2015 Return: Wed Oct 14 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
11:30a
OAK
4:07p
4h 37m
nonstop
OAK
4:30a
ORD
8:37a
4h 07m
nonstop
Depart: Tue Oct 13 2015 Return: Tue Oct 20 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
11:30a
OAK
4:01p
4h 31m
nonstop
OAK
4:30a
ORD
8:33a
4h 03m
nonstop
Depart: Wed Oct 14 2015 Return: Tue Oct 20 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
11:30a
OAK
4:01p
4h 31m
nonstop
OAK
4:30a
ORD
8:33a
4h 03m
nonstop
Depart: Sat May 23 2015 Return: Tue Jun 2 2015 Trip spans 11 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: Sat May 16 2015 Trip spans 5 days
American Airlines
American Airlines
ORD
1:00a
OAK
7:22a
6h 22m
1 stop
OAK
12:15p
ORD
6:08p
5h 53m
1 stop
Depart: Sun May 17 2015 Return: Sun May 24 2015 Trip spans 8 days
Delta
Delta
ORD
2:10a
OAK
9:00a
6h 50m
1 stop
OAK
2:00a
ORD
9:26a
7h 26m
1 stop
Depart: Thu Sep 3 2015 Return: Tue Sep 8 2015 Trip spans 6 days
Delta
Delta
MDW
2:43a
OAK
8:53a
6h 10m
1 stop
OAK
4:35p
MDW
3:00a
10h 25m
2 stops
Direct flights CHI to OAK on Southwest
Flight # Depart MDW Arrive OAK Sun Mon Tue Wed Thu Fri Sat Valid Between
1895 8:30 am 11:10 am May 25 - May 25
4985 8:30 am 11:10 am Apr 26 - May 22
4985 8:30 am 11:10 am May 26 - Jun 5
4985 8:30 am 11:10 am May 24 - May 24
1653 8:55 am 11:35 am May 23 - May 23
2636 8:55 am 11:35 am May 9 - May 9
2636 8:55 am 11:35 am May 16 - May 16
2636 8:55 am 11:35 am May 30 - May 30
1572 4:45 pm 7:25 pm May 24 - May 24
1572 4:45 pm 7:25 pm May 25 - May 25
524 4:45 pm 7:25 pm Apr 26 - May 10
524 4:45 pm 7:25 pm May 12 - May 22
524 4:45 pm 7:25 pm May 11 - May 11
524 4:45 pm 7:25 pm May 26 - Jun 5
1998 6:35 pm 9:10 pm May 30 - Jun 6
1998 6:35 pm 9:10 pm Apr 25 - May 16
2024 6:35 pm 9:10 pm May 23 - May 23
1704 7:40 pm 10:20 pm May 24 - May 25
555 7:40 pm 10:20 pm May 26 - Jun 5
555 7:40 pm 10:20 pm Apr 26 - May 22
Airports
Origin

Chicago
only $187
only $348
Destination

Oakland
$187