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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Book cheap flights from Chicago to Oakland

(Round-trip)
Depart: Sat May 20 2017 Return: Tue May 23 2017 Trip spans 4 days
Major Airline
Major Airline
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 16m
nonstop
Depart: Tue May 23 2017 Return: Tue May 30 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 15m
nonstop
Depart: Tue Sep 19 2017 Return: Sat Sep 30 2017 Trip spans 12 days
Delta
Delta
MDW
OAK
10h 42m
2 stops
OAK
MDW
8h 39m
2 stops
Depart: Thu Jun 1 2017 Return: Sat Jun 3 2017 Trip spans 3 days
Major Airline
Major Airline
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 15m
nonstop
Depart: Thu Jun 8 2017 Return: Wed Jun 14 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 15m
nonstop
Depart: Sat Jun 3 2017 Return: Tue Jun 6 2017 Trip spans 4 days
Major Airline
Major Airline
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 15m
nonstop
Depart: Thu May 11 2017 Return: Tue May 16 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 16m
nonstop
Depart: Mon May 15 2017 Return: Tue May 23 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 16m
nonstop
Depart: Sat Jun 3 2017 Return: Mon Jul 3 2017 Trip spans 31 days
Major Airline
Major Airline
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 10m
nonstop
Depart: Thu Aug 31 2017 Return: Sun Sep 3 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 10m
nonstop
Depart: Fri Jun 2 2017 Return: Wed Jun 7 2017 Trip spans 6 days
Delta
Delta
MDW
OAK
8h 05m
1 stop
OAK
MDW
11h 11m
2 stops
Depart: Thu Sep 14 2017 Return: Mon Sep 18 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 00m
nonstop
Depart: Wed May 3 2017 Return: Tue May 9 2017 Trip spans 7 days
Delta
Delta
MDW
OAK
13h 24m
2 stops
OAK
MDW
9h 59m
2 stops
Depart: Sun Aug 27 2017 Return: Mon Aug 28 2017 Trip spans 2 days
Major Airline
Major Airline
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 10m
nonstop
Depart: Sat Jul 15 2017 Return: Tue Jul 18 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 10m
nonstop
Depart: Fri Aug 18 2017 Return: Tue Aug 22 2017 Trip spans 5 days
Delta
Delta
MDW
OAK
11h 25m
2 stops
OAK
MDW
12h 43m
2 stops
Depart: Wed Aug 30 2017 Return: Sun Sep 3 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 10m
nonstop
Depart: Thu Jun 8 2017 Return: Mon Jun 12 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 15m
nonstop
Depart: Fri Sep 1 2017 Return: Tue Sep 5 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 10m
nonstop
Depart: Tue Jul 4 2017 Return: Tue Jul 11 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 10m
nonstop
Direct flights CHI to OAK on Southwest
Flight # Depart MDW Arrive OAK Sun Mon Tue Wed Thu Fri Sat Valid Between
1349 8:10 am 10:45 am Jun 5 - Jun 30
338 8:30 am 11:05 am Apr 26 - Jun 2
1794 8:55 am 11:30 am Jun 4 - Aug 13
3102 9:05 am 11:40 am May 28 - May 28
788 9:05 am 11:40 am Apr 30 - May 21
2891 9:35 am 12:10 pm Apr 29 - Jun 3
403 12:05 pm 2:40 pm Jun 5 - Aug 14
3757 12:35 pm 3:10 pm Jun 4 - Aug 13
1629 3:45 pm 6:20 pm May 29 - May 29
222 3:45 pm 6:20 pm Apr 26 - May 26
222 3:45 pm 6:20 pm May 30 - Jun 2
5391 5:15 pm 7:50 pm Apr 30 - May 28
411 5:40 pm 8:15 pm Jun 5 - Jun 30
5430 5:55 pm 8:30 pm Jun 4 - Aug 13
4490 6:35 pm 9:10 pm Jun 3 - Jun 3
4490 6:35 pm 9:10 pm Apr 29 - May 27
1875 7:40 pm 10:15 pm Apr 26 - Jun 2
1010 7:50 pm 10:25 pm Jun 5 - Aug 14
4677 8:10 pm 10:45 pm May 28 - May 28
4677 8:10 pm 10:45 pm Apr 30 - May 7
4677 8:10 pm 10:45 pm May 14 - May 21
1369 8:20 pm 10:55 pm Jun 4 - Jun 25
* 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.

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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
only $209
only $272
Destination

Oakland
$209
Airlines Airline reviews

133 travelers who booked a flight from Chicago to Oakland rated their chosen airlines with an average of 5.3.

Overall
5.6
Boarding
5.9
Crew
6.5
Comfort
5.0
Food
3.9
Entertainment
3.7