Find Cheap Flights from Chicago to Oakland (CHI - OAK)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Chicago to Oakland

(Round-trip)
Depart: Wed Aug 16 2017 Return: Tue Aug 22 2017 Trip spans 7 days
Major Airline
Major Airline
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 10m
nonstop
Depart: Tue Aug 22 2017 Return: Wed Aug 30 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 10m
nonstop
Depart: Thu Sep 28 2017 Return: Mon Oct 2 2017 Trip spans 5 days
Delta
Delta
MDW
OAK
9h 25m
2 stops
OAK
MDW
8h 49m
2 stops
Depart: Thu Aug 31 2017 Return: Tue Sep 5 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 10m
nonstop
Depart: Thu Sep 7 2017 Return: Sat Sep 16 2017 Trip spans 10 days
Major Airline
Major Airline
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 11m
nonstop
Depart: Tue Sep 12 2017 Return: Sat Sep 16 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 11m
nonstop
Depart: Thu Sep 14 2017 Return: Mon Sep 18 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 11m
nonstop
Depart: Thu Oct 5 2017 Return: Sun Oct 15 2017 Trip spans 11 days
Major Airline
Major Airline
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 11m
nonstop
Depart: Thu Jul 13 2017 Return: Mon Jul 17 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 10m
nonstop
Depart: Fri Sep 8 2017 Return: Wed Sep 13 2017 Trip spans 6 days
Delta
Delta
MDW
OAK
13h 20m
2 stops
OAK
MDW
14h 15m
2 stops
Depart: Fri Aug 18 2017 Return: Sun Aug 27 2017 Trip spans 10 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 10m
nonstop
Depart: Fri Oct 6 2017 Return: Mon Oct 9 2017 Trip spans 4 days
Major Airline
Major Airline
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 11m
nonstop
Depart: Fri Nov 3 2017 Return: Tue Nov 7 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 11m
nonstop
Depart: Sat Nov 4 2017 Return: Sun Nov 5 2017 Trip spans 2 days
Major Airline
Major Airline
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 11m
nonstop
Depart: Thu Oct 5 2017 Return: Sun Oct 15 2017 Trip spans 11 days
Delta
Delta
MDW
OAK
10h 42m
2 stops
OAK
MDW
8h 49m
2 stops
Depart: Thu Jul 13 2017 Return: Tue Jul 18 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 10m
nonstop
Depart: Fri Nov 3 2017 Return: Tue Nov 7 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 11m
nonstop
Depart: Fri Nov 3 2017 Return: Tue Nov 7 2017 Trip spans 5 days
Delta
Delta
MDW
OAK
11h 37m
2 stops
OAK
MDW
12h 12m
2 stops
Depart: Mon Dec 4 2017 Return: Fri Dec 8 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
OAK
10h 04m
1 stop
OAK
ORD
5h 56m
1 stop
Depart: Wed Jun 28 2017 Return: Tue Jul 11 2017 Trip spans 14 days
Spirit Airlines
Spirit Airlines
ORD
OAK
10h 32m
1 stop
OAK
ORD
4h 10m
nonstop
Direct flights CHI to OAK on Southwest
Flight # Depart MDW Arrive OAK Sun Mon Tue Wed Thu Fri Sat Valid Between
1349 8:10 am 10:45 am Jun 21 - Jun 30
1349 8:10 am 10:45 am Jul 4 - Aug 14
1794 8:55 am 11:30 am Jun 25 - Aug 13
5978 9:40 am 12:10 pm Jun 24 - Aug 12
403 12:05 pm 2:40 pm Jun 21 - Aug 14
3757 12:35 pm 3:10 pm Jun 25 - Aug 13
4454 1:50 pm 4:30 pm Jun 24 - Aug 12
3733 4:20 pm 6:55 pm Jul 3 - Jul 3
4234 5:25 pm 8:00 pm Jul 8 - Aug 12
4234 5:25 pm 8:00 pm Jun 24 - Jul 1
411 5:40 pm 8:15 pm Jul 5 - Aug 14
411 5:40 pm 8:15 pm Jun 21 - Jun 30
3957 5:50 pm 8:25 pm Jul 4 - Jul 4
5430 5:55 pm 8:30 pm Jun 25 - Aug 13
1010 7:50 pm 10:25 pm Jun 21 - Aug 14
5345 7:55 pm 10:30 pm Jul 8 - Aug 12
1369 8:20 pm 10:55 pm Jul 2 - Aug 13
6114 8:50 pm 11:25 pm Jul 1 - Jul 1
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

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Airports
Origin

Chicago
only $209
only $272
Destination

Oakland
$209
Airlines Airline reviews

162 travelers who booked a flight from Chicago to Oakland rated their chosen airlines with an average of 5.4.

Overall
5.7
Boarding
5.9
Crew
6.5
Comfort
5.2
Food
3.9
Entertainment
3.7