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 30 2016 Return: Wed Sep 7 2016 Trip spans 9 days
Depart: Sat Sep 17 2016 Return: Wed Sep 21 2016 Trip spans 5 days
Depart: Sun Jan 29 2017 Return: Sat Feb 4 2017 Trip spans 7 days
Depart: Sat Dec 10 2016 Return: Thu Dec 15 2016 Trip spans 6 days
Depart: Wed Sep 14 2016 Return: Tue Sep 20 2016 Trip spans 7 days
Depart: Tue Sep 20 2016 Return: Wed Sep 21 2016 Trip spans 2 days
Depart: Sat Oct 1 2016 Return: Tue Oct 4 2016 Trip spans 4 days
Depart: Tue Sep 13 2016 Return: Sun Sep 18 2016 Trip spans 6 days
Depart: Wed Oct 12 2016 Return: Sat Oct 22 2016 Trip spans 11 days
Depart: Wed Nov 9 2016 Return: Tue Nov 15 2016 Trip spans 7 days
Depart: Tue Nov 1 2016 Return: Sun Nov 6 2016 Trip spans 6 days
Depart: Sat Oct 15 2016 Return: Fri Oct 21 2016 Trip spans 7 days
Depart: Sat Oct 29 2016 Return: Mon Nov 7 2016 Trip spans 10 days
Depart: Wed Feb 1 2017 Return: Sun Feb 5 2017 Trip spans 5 days
Depart: Sat Oct 29 2016 Return: Mon Oct 31 2016 Trip spans 3 days
Depart: Tue Nov 1 2016 Return: Mon Nov 7 2016 Trip spans 7 days
Depart: Wed Nov 9 2016 Return: Mon Nov 14 2016 Trip spans 6 days
Depart: Fri Oct 14 2016 Return: Sun Oct 16 2016 Trip spans 3 days
Depart: Fri Sep 30 2016 Return: Sun Oct 2 2016 Trip spans 3 days
Depart: Sun Sep 4 2016 Return: Wed Sep 7 2016 Trip spans 4 days
Direct flights CHI to OAK on Southwest
Flight # Depart MDW Arrive OAK Sun Mon Tue Wed Thu Fri Sat Valid Between
2654 8:30 am 11:10 am Sep 6 - Sep 30
2654 8:30 am 11:10 am Aug 21 - Sep 2
5347 8:40 am 11:20 am Sep 4 - Sep 4
3 9:05 am 11:40 am Sep 3 - Sep 3
5588 9:05 am 11:40 am Sep 10 - Nov 5
2366 12:55 pm 3:25 pm Sep 4 - Sep 4
448 12:55 pm 3:25 pm Aug 21 - Sep 2
448 12:55 pm 3:25 pm Sep 5 - Sep 30
3813 2:15 pm 4:50 pm Sep 10 - Oct 1
3813 2:15 pm 4:50 pm Sep 3 - Sep 3
406 4:35 pm 7:10 pm Sep 5 - Sep 5
5430 4:35 pm 7:10 pm Sep 11 - Sep 25
618 4:35 pm 7:10 pm Aug 22 - Sep 2
618 4:35 pm 7:10 pm Sep 6 - Sep 30
2284 7:00 pm 9:30 pm Sep 10 - Oct 1
1243 7:40 pm 10:20 pm Sep 6 - Sep 30
1243 7:40 pm 10:20 pm Aug 21 - Sep 2
195 7:40 pm 10:20 pm Sep 4 - Sep 5
* 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 $177
only $222
Destination

Oakland
$177