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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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago to Oakland

(Round-trip)
Depart: Fri Apr 27 2018 Return: Tue May 1 2018 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 10m
nonstop
Depart: Sat Nov 4 2017 Return: Wed Nov 8 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Fri Oct 27 2017 Return: Tue Oct 31 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Tue Oct 31 2017 Return: Tue Nov 7 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Wed Nov 1 2017 Return: Wed Nov 8 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Wed Nov 1 2017 Return: Wed Nov 8 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Sat Nov 4 2017 Return: Tue Nov 7 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Wed Oct 25 2017 Return: Tue Oct 31 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Tue Oct 31 2017 Return: Sat Nov 4 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Wed Nov 1 2017 Return: Tue Nov 7 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Mon Nov 6 2017 Return: Tue Nov 7 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Fri Nov 3 2017 Return: Wed Nov 8 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Wed Nov 1 2017 Return: Mon Nov 6 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Sat Nov 4 2017 Return: Mon Nov 6 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Thu Nov 2 2017 Return: Wed Nov 8 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Wed Oct 18 2017 Return: Tue Oct 31 2017 Trip spans 14 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Tue Oct 24 2017 Return: Sat Nov 4 2017 Trip spans 12 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Wed Oct 25 2017 Return: Sat Nov 4 2017 Trip spans 11 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Sat Oct 28 2017 Return: Sat Nov 4 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Tue Oct 31 2017 Return: Wed Nov 1 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Direct flights CHI to OAK on Southwest
Flight # Depart MDW Arrive OAK Sun Mon Tue Wed Thu Fri Sat Valid Between
5915 8:10 am 11:00 am Nov 17 - Nov 22
3359 8:15 am 11:05 am Nov 23 - Nov 23
654 8:15 am 11:05 am Nov 20 - Nov 24
654 8:15 am 11:05 am Nov 6 - Nov 16
6645 8:20 am 11:15 am Nov 18 - Nov 18
1278 8:30 am 11:10 am Oct 9 - Nov 3
3925 8:40 am 11:25 am Oct 7 - Oct 28
815 8:45 am 11:30 am Nov 4 - Nov 4
2283 8:50 am 11:40 am Nov 11 - Nov 11
3689 9:00 am 11:40 am Oct 22 - Oct 29
3821 9:00 am 11:50 am Nov 5 - Nov 19
5072 10:15 am 1:00 pm Nov 17 - Nov 22
156 11:10 am 1:50 pm Oct 9 - Nov 3
1940 11:40 am 2:25 pm Nov 6 - Nov 16
1940 11:40 am 2:25 pm Nov 24 - Nov 24
1940 11:40 am 2:25 pm Nov 20 - Nov 23
5008 11:55 am 2:35 pm Oct 7 - Oct 28
4554 12:35 pm 3:20 pm Nov 18 - Nov 25
1342 2:05 pm 4:45 pm Nov 4 - Nov 4
4171 4:45 pm 7:20 pm Oct 8 - Oct 29
2741 6:00 pm 8:50 pm Nov 5 - Nov 19
6794 6:05 pm 8:55 pm Nov 17 - Nov 22
1600 6:15 pm 9:05 pm Nov 11 - Nov 11
5163 6:20 pm 9:00 pm Oct 7 - Oct 28
2727 6:30 pm 9:10 pm Nov 4 - Nov 4
4697 6:40 pm 9:20 pm Oct 9 - Oct 30
4697 6:40 pm 9:20 pm Nov 1 - Nov 3
1306 7:20 pm 10:10 pm Nov 6 - Nov 16
1306 7:20 pm 10:10 pm Nov 20 - Nov 20
3398 7:25 pm 10:10 pm Nov 24 - Dec 1
5904 8:05 pm 10:50 pm Oct 8 - Oct 29
1489 8:10 pm 11:00 pm Nov 18 - Nov 25
924 8:20 pm 11:05 pm Nov 17 - Nov 22
578 8:40 pm 11:20 pm Oct 9 - Oct 30
578 8:40 pm 11:20 pm Nov 1 - Nov 3
329 8:50 pm 11:30 pm Oct 31 - Oct 31
3257 8:55 pm 11:50 pm Nov 5 - Nov 19
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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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.

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Airports
Origin

Chicago
$133
Destination

Oakland
$133
Airlines Airline reviews

195 travelers who booked a flight from Chicago to Oakland rated their chosen airlines with an average of 5.5.

Overall
5.8
Boarding
6.1
Crew
6.6
Comfort
5.2
Food
4.1
Entertainment
3.9