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

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youth
12-17
Child
2-11
Seat Infant
under 2
Lap Infant
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago to Oakland

(Round-trip)
Depart: Wed Aug 26 2015 Return: Wed Sep 9 2015 Trip spans 15 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 Aug 27 2015 Return: Wed Sep 9 2015 Trip spans 14 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: Wed Sep 9 2015 Trip spans 13 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 Sep 22 2015 Trip spans 42 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 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: Sat Sep 12 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
10:45a
OAK
3:17p
4h 32m
nonstop
OAK
4:29a
ORD
8:33a
4h 04m
nonstop
Depart: Sat Sep 12 2015 Return: Tue Sep 15 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: Tue Sep 15 2015 Return: Wed Sep 16 2015 Trip spans 2 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: Sat Sep 19 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 19 2015 Return: Tue Sep 22 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: 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: 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
4:29a
ORD
8:33a
4h 04m
nonstop
Depart: Wed Sep 30 2015 Return: Sat Oct 3 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 Aug 22 2015 Return: Wed Aug 26 2015 Trip spans 5 days
US Airways
US Airways
ORD
1:10a
OAK
7:17a
6h 07m
1 stop
OAK
2:10a
ORD
9:59a
7h 49m
1 stop
Depart: Tue Aug 18 2015 Return: Wed Aug 19 2015 Trip spans 2 days
Delta
Delta
MDW
2:40a
OAK
8:39a
5h 59m
1 stop
OAK
12:37p
MDW
6:03p
5h 26m
1 stop
Depart: Tue Jan 5 2016 Return: Sat Jan 9 2016 Trip spans 5 days
American Airlines
American Airlines
ORD
2:30a
OAK
8:46a
6h 16m
1 stop
OAK
1:00a
ORD
7:49a
6h 49m
1 stop
Depart: Sat Jan 2 2016 Return: Sat Jan 9 2016 Trip spans 8 days
Alaska Airlines
Alaska Airlines
ORD
1:00a
OAK
9:13a
8h 13m
1 stop
OAK
8:15a
ORD
4:59p
8h 44m
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 28 - Aug 7
30 8:30 am 11:10 am Aug 1 - Aug 8
1315 8:35 am 11:15 am Aug 9 - Sep 4
1495 9:05 am 11:45 am Sep 5 - Sep 5
25 9:05 am 11:45 am Aug 15 - Aug 29
3331 12:15 pm 2:50 pm Jul 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
493 12:50 pm 3:30 pm Aug 31 - Sep 4
897 12:50 pm 3:30 pm Sep 6 - Sep 6
2026 1:35 pm 4:15 pm Aug 15 - Aug 29
5182 1:35 pm 4:15 pm Sep 5 - Sep 5
4361 3:45 pm 6:20 pm Aug 1 - 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 Aug 1 - Aug 8
248 6:20 pm 8:55 pm Jul 28 - Aug 7
1862 7:05 pm 9:40 pm Aug 1 - Aug 8
1324 7:20 pm 10:00 pm Aug 15 - Aug 29
2489 7:40 pm 10:20 pm Aug 9 - Oct 30
2342 8:05 pm 10:45 pm Jul 28 - Aug 7
Airports
Origin

Chicago
only $187
only $304
Destination

Oakland
$187