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: Sat Oct 8 2016 Return: Wed Oct 12 2016 Trip spans 5 days
Depart: Wed Aug 24 2016 Return: Sun Aug 28 2016 Trip spans 5 days
Depart: Sat Sep 3 2016 Return: Sun Sep 4 2016 Trip spans 2 days
Depart: Fri Dec 2 2016 Return: Sun Dec 4 2016 Trip spans 3 days
Depart: Fri Sep 9 2016 Return: Sun Sep 11 2016 Trip spans 3 days
Depart: Wed Sep 28 2016 Return: Mon Oct 3 2016 Trip spans 6 days
Depart: Sat Aug 27 2016 Return: Sun Sep 25 2016 Trip spans 30 days
Depart: Thu Sep 22 2016 Return: Sat Oct 1 2016 Trip spans 10 days
Depart: Mon Oct 24 2016 Return: Fri Oct 28 2016 Trip spans 5 days
Depart: Fri Sep 23 2016 Return: Tue Sep 27 2016 Trip spans 5 days
Depart: Thu Oct 20 2016 Return: Sun Oct 23 2016 Trip spans 4 days
Depart: Tue Nov 1 2016 Return: Fri Nov 4 2016 Trip spans 4 days
Depart: Tue Aug 23 2016 Return: Tue Aug 30 2016 Trip spans 8 days
Depart: Wed Aug 31 2016 Return: Mon Sep 5 2016 Trip spans 6 days
Depart: Mon Oct 3 2016 Return: Sun Oct 9 2016 Trip spans 7 days
Depart: Thu Jan 12 2017 Return: Mon Jan 16 2017 Trip spans 5 days
Depart: Tue Aug 23 2016 Return: Wed Aug 31 2016 Trip spans 9 days
Depart: Thu Aug 25 2016 Return: Tue Aug 30 2016 Trip spans 6 days
Depart: Sat Sep 24 2016 Return: Mon Sep 26 2016 Trip spans 3 days
Depart: Fri Sep 9 2016 Return: Sun Sep 11 2016 Trip spans 3 days
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 Jul 26 - Aug 5
5044 8:15 am 10:45 am Aug 6 - Aug 6
2654 8:30 am 11:10 am Aug 7 - Sep 2
3 9:05 am 11:40 am Sep 3 - Sep 3
5588 9:05 am 11:40 am Aug 13 - Aug 27
448 12:55 pm 3:25 pm Aug 7 - Aug 12
448 12:55 pm 3:25 pm Aug 14 - Sep 2
3459 2:00 pm 4:35 pm Jul 26 - Aug 5
3813 2:15 pm 4:50 pm Sep 3 - Sep 3
3813 2:15 pm 4:50 pm Aug 13 - Aug 27
5430 4:35 pm 7:10 pm Aug 7 - Aug 28
618 4:35 pm 7:10 pm Aug 8 - Sep 2
6176 5:15 pm 7:50 pm Aug 6 - Aug 6
5643 6:45 pm 9:20 pm Aug 1 - Aug 5
5643 6:45 pm 9:20 pm Jul 26 - Aug 4
2284 7:00 pm 9:30 pm Aug 13 - Aug 27
1050 7:25 pm 10:00 pm Aug 6 - Aug 6
1243 7:40 pm 10:20 pm Aug 7 - Sep 2
1561 9:45 pm 12:20 am Jul 26 - Aug 5
6247 9:55 pm 12:30 am Aug 6 - Aug 6
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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

Here's why:

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

We compile tonnes 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 can'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.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Chicago
only $180
only $239
Destination

Oakland
$180