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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 Aug 11 2015 Return: Tue Aug 18 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 12 2015 Return: Tue Aug 18 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 1 2015 Return: Wed Sep 16 2015 Trip spans 16 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:17p
4h 32m
nonstop
OAK
4:30a
ORD
8:33a
4h 03m
nonstop
Depart: Wed Sep 2 2015 Return: Wed Sep 16 2015 Trip spans 15 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:17p
4h 32m
nonstop
OAK
4:30a
ORD
8:33a
4h 03m
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
4:30a
ORD
8:33a
4h 03m
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
4:30a
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: Tue Nov 17 2015 Return: Tue Dec 1 2015 Trip spans 15 days
Spirit Airlines
Spirit Airlines
ORD
10:27a
OAK
3:02p
4h 35m
nonstop
OAK
3:50a
ORD
7:50a
4h 00m
nonstop
Depart: Wed Nov 18 2015 Return: Tue Dec 1 2015 Trip spans 14 days
Spirit Airlines
Spirit Airlines
ORD
10:27a
OAK
3:02p
4h 35m
nonstop
OAK
3:50a
ORD
7:50a
4h 00m
nonstop
Depart: Tue Aug 18 2015 Return: Tue Aug 25 2015 Trip spans 8 days
US Airways
US Airways
ORD
1:10a
OAK
7:17a
6h 07m
1 stop
OAK
12:10p
ORD
6:12p
6h 02m
1 stop
Depart: Wed Aug 19 2015 Return: Tue Aug 25 2015 Trip spans 7 days
US Airways
US Airways
ORD
1:10a
OAK
7:17a
6h 07m
1 stop
OAK
12:10p
ORD
6:12p
6h 02m
1 stop
Depart: Thu Aug 20 2015 Return: Tue Aug 25 2015 Trip spans 6 days
US Airways
US Airways
ORD
1:10a
OAK
7:17a
6h 07m
1 stop
OAK
12:10p
ORD
6:12p
6h 02m
1 stop
Depart: Thu Aug 27 2015 Return: Tue Sep 1 2015 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:17p
4h 32m
nonstop
OAK
4:39a
ORD
8:44a
4h 05m
nonstop
Depart: Fri Aug 28 2015 Return: Tue Sep 1 2015 Trip spans 5 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: Thu Sep 10 2015 Return: Wed Sep 16 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: Thu May 28 2015 Return: Fri Jun 19 2015 Trip spans 23 days
Delta
Delta
ORD
12:30p
OAK
9:03p
8h 33m
1 stop
OAK
12:39p
ORD
6:04p
5h 25m
1 stop
Depart: Mon Jun 1 2015 Return: Tue Jun 9 2015 Trip spans 9 days
Delta
Delta
MDW
8:35a
OAK
8:04p
11h 29m
2 stops
OAK
4:48p
MDW
2:33a
9h 45m
2 stops
Direct flights CHI to OAK on Southwest
Flight # Depart MDW Arrive OAK Sun Mon Tue Wed Thu Fri Sat Valid Between
1890 8:10 am 10:45 am Jul 3 - Jul 3
527 8:10 am 10:45 am Jun 7 - Jul 2
143 8:30 am 11:10 am Jul 4 - Jul 4
30 8:30 am 11:10 am Jun 13 - Jun 27
4985 8:30 am 11:10 am May 31 - Jun 5
2636 8:55 am 11:35 am Jun 6 - Jun 6
3331 12:15 pm 2:50 pm Jun 7 - Aug 7
4102 3:00 pm 5:35 pm Jul 4 - Jul 4
4361 3:45 pm 6:20 pm Jun 13 - Jun 27
524 4:45 pm 7:25 pm May 31 - Jun 5
3074 5:30 pm 8:05 pm Jun 13 - Jun 27
5252 5:30 pm 8:05 pm Jul 4 - Jul 4
248 6:20 pm 8:55 pm Jun 7 - Jul 2
991 6:20 pm 8:55 pm Jul 3 - Jul 3
1998 6:35 pm 9:10 pm May 30 - Jun 6
1862 7:05 pm 9:40 pm Jun 13 - Jun 27
555 7:40 pm 10:20 pm May 31 - Jun 5
2342 8:05 pm 10:45 pm Jun 7 - Jun 12
2342 8:05 pm 10:45 pm Jun 14 - Aug 7
Airports
Origin

Chicago
only $237
only $426
Destination

Oakland
$237