Find Deals on 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: Thu May 12 2016 Return: Sat May 21 2016 Trip spans 10 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 37m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Tue Aug 16 2016 Return: Wed Aug 17 2016 Trip spans 2 days
Major Airline
Major Airline
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 11m
nonstop
Depart: Thu Aug 25 2016 Return: Mon Aug 29 2016 Trip spans 5 days
Delta
Delta
MDW
OAK
9h 20m
1 stop
OAK
MDW
9h 55m
1 stop
Depart: Wed Jun 8 2016 Return: Wed Jun 22 2016 Trip spans 15 days
Southwest
Southwest
MDW
OAK
4h 35m
nonstop
OAK
MDW
6h 15m
nonstop
Depart: Thu May 19 2016 Return: Sat May 21 2016 Trip spans 3 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 37m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Fri May 13 2016 Return: Sun May 15 2016 Trip spans 3 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 37m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Tue Jun 7 2016 Return: Tue Jun 14 2016 Trip spans 8 days
Alaska Airlines
Alaska Airlines
ORD
OAK
8h 05m
1 stop
OAK
ORD
7h 34m
1 stop
Depart: Wed Aug 31 2016 Return: Wed Sep 7 2016 Trip spans 8 days
Major Airline
Major Airline
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 11m
nonstop
Depart: Thu Oct 6 2016 Return: Mon Oct 10 2016 Trip spans 5 days
Major Airline
Major Airline
ORD
OAK
4h 33m
nonstop
OAK
ORD
4h 05m
nonstop
Depart: Tue Aug 9 2016 Return: Tue Aug 16 2016 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 11m
nonstop
Depart: Thu Nov 3 2016 Return: Sun Nov 6 2016 Trip spans 4 days
Major Airline
Major Airline
ORD
OAK
4h 33m
nonstop
OAK
ORD
4h 05m
nonstop
Depart: Thu Sep 15 2016 Return: Tue Sep 20 2016 Trip spans 6 days
Delta
Delta
MDW
OAK
11h 03m
1 stop
OAK
MDW
7h 50m
1 stop
Depart: Tue Sep 6 2016 Return: Tue Sep 13 2016 Trip spans 8 days
Southwest
Southwest
MDW
OAK
4h 40m
nonstop
OAK
MDW
4h 00m
nonstop
Depart: Tue Jun 21 2016 Return: Wed Jun 22 2016 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 11m
nonstop
Depart: Tue Jul 12 2016 Return: Tue Aug 9 2016 Trip spans 29 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 11m
nonstop
Depart: Wed Aug 24 2016 Return: Wed Aug 31 2016 Trip spans 8 days
Southwest
Southwest
MDW
OAK
4h 40m
nonstop
OAK
MDW
4h 05m
nonstop
Depart: Wed Oct 26 2016 Return: Mon Oct 31 2016 Trip spans 6 days
Major Airline
Major Airline
MDW
OAK
11h 03m
1 stop
OAK
MDW
9h 57m
1 stop
Depart: Wed Jul 13 2016 Return: Tue Jul 19 2016 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 11m
nonstop
Depart: Sat May 28 2016 Return: Mon May 30 2016 Trip spans 3 days
Southwest
Southwest
MDW
OAK
4h 40m
nonstop
OAK
MDW
4h 15m
nonstop
Depart: Tue Jul 19 2016 Return: Tue Aug 2 2016 Trip spans 15 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 11m
nonstop
Direct flights CHI to OAK on Southwest
Flight # Depart MDW Arrive OAK Sun Mon Tue Wed Thu Fri Sat Valid Between
424 7:45 am 10:15 am Jun 5 - Jul 1
5044 8:15 am 10:45 am Jun 11 - Jul 30
2810 8:30 am 11:05 am May 31 - Jun 3
2810 8:30 am 11:05 am Apr 28 - May 27
3535 8:30 am 11:05 am May 29 - May 30
2315 8:45 am 11:20 am Apr 30 - Jun 4
3459 2:00 pm 4:35 pm Jun 5 - Jul 1
1181 4:35 pm 7:10 pm May 31 - Jun 3
1181 4:35 pm 7:10 pm Apr 28 - May 27
2445 4:35 pm 7:10 pm May 30 - May 30
2493 4:35 pm 7:10 pm May 29 - May 29
6176 5:15 pm 7:50 pm Jun 11 - Jul 30
5643 6:45 pm 9:20 pm Jun 5 - Jun 12
595 7:15 pm 9:50 pm Jun 11 - Jun 11
1648 7:30 pm 10:10 pm Apr 30 - Jun 4
2320 7:45 pm 10:20 pm May 29 - May 30
2771 7:45 pm 10:20 pm Apr 28 - May 27
2771 7:45 pm 10:20 pm May 31 - Jun 3
1561 9:45 pm 12:20 am Jun 5 - Jul 1
5161 9:55 pm 12:30 am Jun 11 - Jul 30
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We make every attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

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

We aggregate tons of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we don't guarantee prices we find.

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.

More questions or if you have a bad price to report to us
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Airports
Origin

Chicago
only $187
only $274
Destination

Oakland
$187