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 Sep 9 2017 Return: Sun Sep 10 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Tue Sep 12 2017 Return: Sat Sep 16 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Sat Aug 26 2017 Return: Tue Sep 19 2017 Trip spans 25 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 35m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Fri Sep 8 2017 Return: Sun Sep 10 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Wed Aug 30 2017 Return: Wed Sep 6 2017 Trip spans 8 days
Delta
Delta
MDW
OAK
11h 17m
2 stops
OAK
MDW
14h 16m
2 stops
Depart: Thu Oct 5 2017 Return: Tue Oct 10 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: Thu Sep 7 2017 Return: Fri Sep 8 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
4h 12m
nonstop
Depart: Tue Oct 31 2017 Return: Wed Nov 8 2017 Trip spans 9 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: Thu Nov 23 2017 Return: Tue Nov 28 2017 Trip spans 6 days
Alaska Airlines
Alaska Airlines
ORD
OAK
11h 41m
1 stop
OAK
ORD
7h 07m
1 stop
Depart: Sat Sep 2 2017 Return: Sat Sep 9 2017 Trip spans 8 days
Delta
Delta
MDW
OAK
8h 12m
2 stops
OAK
MDW
14h 54m
2 stops
Depart: Fri Oct 6 2017 Return: Mon Oct 9 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 38m
nonstop
OAK
ORD
14h 37m
1 stop
Depart: Tue Sep 26 2017 Return: Fri Sep 29 2017 Trip spans 4 days
Delta
Delta
MDW
OAK
9h 56m
2 stops
OAK
MDW
12h 02m
2 stops
Depart: Sat Oct 7 2017 Return: Wed Oct 11 2017 Trip spans 5 days
Delta
Delta
MDW
OAK
9h 50m
2 stops
OAK
MDW
11h 08m
2 stops
Depart: Mon Aug 28 2017 Return: Sun Sep 3 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
OAK
13h 14m
1 stop
OAK
ORD
4h 10m
nonstop
Depart: Thu Nov 2 2017 Return: Thu Nov 9 2017 Trip spans 8 days
Delta
Delta
MDW
OAK
12h 21m
2 stops
OAK
MDW
14h 15m
2 stops
Depart: Sat Dec 30 2017 Return: Fri Jan 5 2018 Trip spans 7 days
Alaska Airlines
Alaska Airlines
ORD
OAK
19h 57m
1 stop
OAK
ORD
8h 17m
1 stop
Depart: Mon Dec 11 2017 Return: Thu Dec 14 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
OAK
10h 34m
1 stop
OAK
ORD
12h 43m
1 stop
Depart: Thu Aug 24 2017 Return: Tue Aug 29 2017 Trip spans 6 days
Delta
Delta
MDW
OAK
11h 12m
2 stops
OAK
MDW
12h 51m
2 stops
Direct flights CHI to OAK on Southwest
Flight # Depart MDW Arrive OAK Sun Mon Tue Wed Thu Fri Sat Valid Between
1905 8:25 am 11:00 am Sep 4 - Sep 4
1905 8:25 am 11:00 am Aug 16 - Sep 1
1905 8:30 am 11:05 am Sep 5 - Sep 29
2851 8:45 am 11:25 am Sep 2 - Sep 23
2851 8:50 am 11:30 am Aug 19 - Aug 26
3137 8:55 am 11:30 am Sep 3 - Sep 3
4583 8:55 am 11:30 am Aug 20 - Aug 27
4583 8:55 am 11:30 am Sep 10 - Sep 24
1834 12:45 pm 3:15 pm Aug 16 - Sep 15
1834 12:45 pm 3:15 pm Sep 18 - Sep 29
1124 1:10 pm 3:40 pm Sep 3 - Sep 3
3121 1:10 pm 3:40 pm Sep 10 - Sep 24
3121 1:10 pm 3:40 pm Aug 20 - Aug 27
2813 1:25 pm 3:55 pm Sep 9 - Sep 23
2813 1:25 pm 3:55 pm Aug 19 - Aug 26
2813 1:25 pm 3:55 pm Sep 2 - Sep 2
1062 5:40 pm 8:15 pm Sep 4 - Sep 4
6013 5:45 pm 8:20 pm Sep 5 - Sep 29
6013 5:45 pm 8:20 pm Aug 16 - Sep 1
2632 6:30 pm 9:00 pm Sep 9 - Sep 23
2632 6:30 pm 9:00 pm Aug 19 - Aug 26
4170 6:55 pm 9:25 pm Sep 3 - Sep 3
4725 6:55 pm 9:25 pm Sep 10 - Sep 24
4725 6:55 pm 9:25 pm Aug 20 - Aug 27
1809 7:40 pm 10:15 pm Aug 16 - Sep 1
1809 7:40 pm 10:15 pm Sep 4 - Sep 4
1809 7:40 pm 10:15 pm Sep 5 - Sep 29
* 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.

If you have more questions or if you have a bad price to report to us,
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Airports
Origin

Chicago
only $100
only $282
Destination

Oakland
$100
Airlines Airline reviews

184 travelers who booked a flight from Chicago to Oakland rated their chosen airlines with an average of 5.4.

Overall
5.7
Boarding
6.0
Crew
6.5
Comfort
5.1
Food
3.9
Entertainment
3.8