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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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 23 2016 Return: Sun Aug 28 2016 Trip spans 6 days
Depart: Thu Sep 1 2016 Return: Wed Sep 7 2016 Trip spans 7 days
Depart: Tue Oct 4 2016 Return: Tue Oct 11 2016 Trip spans 8 days
Depart: Sun Sep 4 2016 Return: Tue Sep 20 2016 Trip spans 17 days
Depart: Sat Aug 27 2016 Return: Tue Sep 6 2016 Trip spans 11 days
Depart: Wed Aug 24 2016 Return: Mon Aug 29 2016 Trip spans 6 days
Depart: Mon Sep 19 2016 Return: Fri Sep 23 2016 Trip spans 5 days
Depart: Sat Sep 3 2016 Return: Sat Sep 10 2016 Trip spans 8 days
Depart: Wed Oct 19 2016 Return: Tue Oct 25 2016 Trip spans 7 days
Depart: Fri Sep 30 2016 Return: Mon Oct 10 2016 Trip spans 11 days
Depart: Sun Oct 30 2016 Return: Sun Nov 6 2016 Trip spans 8 days
Depart: Thu Oct 27 2016 Return: Mon Oct 31 2016 Trip spans 5 days
Depart: Thu Nov 3 2016 Return: Sun Nov 6 2016 Trip spans 4 days
Depart: Wed Nov 16 2016 Return: Thu Nov 17 2016 Trip spans 2 days
Depart: Tue Sep 13 2016 Return: Tue Sep 27 2016 Trip spans 15 days
Depart: Wed Aug 31 2016 Return: Sat Sep 10 2016 Trip spans 11 days
Depart: Thu Dec 8 2016 Return: Mon Dec 12 2016 Trip spans 5 days
Depart: Fri Sep 2 2016 Return: Thu Sep 15 2016 Trip spans 14 days
Depart: Sat Jun 18 2016 Return: Sun Jul 24 2016 Trip spans 37 days
Depart: Fri Oct 21 2016 Return: Tue Nov 1 2016 Trip spans 12 days
Direct flights CHI to OAK on Southwest
Flight # Depart MDW Arrive OAK Sun Mon Tue Wed Thu Fri Sat Valid Between
1423 7:45 am 10:15 am Jul 3 - Jul 4
424 7:45 am 10:15 am Jun 5 - Jul 1
424 7:45 am 10:15 am Jul 5 - Aug 5
5044 8:15 am 10:45 am Jun 11 - Jul 30
2825 2:00 pm 4:35 pm Jul 3 - Jul 4
3459 2:00 pm 4:35 pm Jul 5 - Aug 5
3459 2:00 pm 4:35 pm Jun 5 - Jul 1
205 4:10 pm 6:45 pm Jul 3 - Jul 3
6176 5:15 pm 7:50 pm Jun 11 - Jul 30
3062 6:10 pm 8:45 pm Jul 3 - Jul 4
5643 6:45 pm 9:20 pm Jun 13 - Jun 13
5643 6:45 pm 9:20 pm Jun 14 - Jun 26
5643 6:45 pm 9:20 pm Jun 27 - Jun 27
5643 6:45 pm 9:20 pm Jun 28 - Jul 8
5643 6:45 pm 9:20 pm Jun 5 - Jun 12
595 7:15 pm 9:50 pm Jul 9 - Jul 30
595 7:15 pm 9:50 pm Jun 11 - Jun 11
595 7:15 pm 9:50 pm Jun 18 - Jun 25
1050 7:25 pm 10:00 pm Jul 2 - Jul 2
1561 9:45 pm 12:20 am Jun 5 - Jul 1
1561 9:45 pm 12:20 am Jul 5 - Aug 5
6389 9:45 pm 12:20 am Jul 4 - Jul 4
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 $207
only $312
Destination

Oakland
$207