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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Book cheap flights from Chicago to Oakland

(Round-trip)
Depart: Mon Oct 3 2016 Return: Wed Oct 5 2016 Trip spans 3 days
Major Airline
Major Airline
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 09m
nonstop
Depart: Tue Oct 11 2016 Return: Tue Oct 18 2016 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 09m
nonstop
Depart: Fri Dec 2 2016 Return: Sat Dec 10 2016 Trip spans 9 days
American Airlines
American Airlines
ORD
OAK
8h 57m
1 stop
OAK
ORD
8h 00m
1 stop
Depart: Sat Feb 11 2017 Return: Tue Feb 14 2017 Trip spans 4 days
Southwest
Southwest
MDW
OAK
4h 45m
nonstop
OAK
MDW
4h 10m
nonstop
Depart: Tue Dec 13 2016 Return: Tue Jan 10 2017 Trip spans 29 days
Delta
Delta
ORD
OAK
6h 19m
1 stop
OAK
ORD
7h 24m
1 stop
Depart: Tue Oct 18 2016 Return: Wed Oct 19 2016 Trip spans 2 days
Major Airline
Major Airline
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 09m
nonstop
Depart: Tue Oct 11 2016 Return: Tue Oct 18 2016 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 09m
nonstop
Depart: Wed Oct 26 2016 Return: Tue Nov 1 2016 Trip spans 7 days
Major Airline
Major Airline
ORD
OAK
4h 36m
2 stops
OAK
ORD
4h 09m
2 stops
Depart: Tue Nov 1 2016 Return: Mon Nov 7 2016 Trip spans 7 days
Major Airline
Major Airline
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 09m
nonstop
Depart: Sat Oct 8 2016 Return: Tue Oct 11 2016 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 09m
nonstop
Depart: Tue Jan 10 2017 Return: Tue Jan 17 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
OAK
9h 02m
1 stop
OAK
ORD
9h 00m
1 stop
Depart: Thu Nov 3 2016 Return: Tue Nov 8 2016 Trip spans 6 days
Major Airline
Major Airline
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 09m
nonstop
Depart: Tue Sep 27 2016 Return: Tue Oct 4 2016 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 09m
nonstop
Depart: Fri Jan 20 2017 Return: Sun Jan 29 2017 Trip spans 10 days
American Airlines
American Airlines
ORD
OAK
7h 14m
1 stop
OAK
ORD
8h 00m
1 stop
Depart: Tue Dec 13 2016 Return: Mon Dec 19 2016 Trip spans 7 days
Delta
Delta
ORD
OAK
6h 19m
1 stop
OAK
ORD
7h 23m
1 stop
Depart: Fri Sep 30 2016 Return: Tue Oct 4 2016 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 09m
nonstop
Depart: Tue Oct 11 2016 Return: Wed Oct 19 2016 Trip spans 9 days
Delta
Delta
MDW
OAK
9h 18m
2 stops
OAK
MDW
11h 24m
2 stops
Depart: Wed Feb 8 2017 Return: Mon Feb 13 2017 Trip spans 6 days
American Airlines
American Airlines
ORD
OAK
7h 12m
1 stop
OAK
ORD
9h 00m
1 stop
Depart: Wed Oct 26 2016 Return: Wed Nov 9 2016 Trip spans 15 days
Major Airline
Major Airline
MDW
OAK
4h 40m
nonstop
OAK
MDW
4h 05m
nonstop
Depart: Mon Nov 21 2016 Return: Fri Nov 25 2016 Trip spans 5 days
Delta
Delta
ORD
OAK
8h 52m
1 stop
OAK
ORD
5h 56m
1 stop
Direct flights CHI to OAK on Southwest
Flight # Depart MDW Arrive OAK Sun Mon Tue Wed Thu Fri Sat Valid Between
2654 8:35 am 11:15 am Nov 1 - Nov 4
2654 8:35 am 11:15 am Oct 2 - Oct 28
2654 8:40 am 11:20 am Oct 30 - Oct 31
5588 9:05 am 11:40 am Sep 24 - Nov 5
2003 12:55 pm 3:25 pm Oct 31 - Oct 31
448 12:55 pm 3:25 pm Oct 2 - Oct 30
448 12:55 pm 3:25 pm Nov 1 - Nov 4
3813 2:15 pm 4:50 pm Oct 8 - Oct 29
5426 4:35 pm 7:10 pm Oct 2 - Oct 30
618 4:35 pm 7:10 pm Nov 1 - Nov 4
618 4:35 pm 7:10 pm Oct 3 - Oct 28
1511 4:45 pm 7:20 pm Oct 31 - Oct 31
2284 7:00 pm 9:35 pm Oct 8 - Nov 5
1755 7:40 pm 10:20 pm Nov 1 - Nov 4
1755 7:40 pm 10:20 pm Oct 2 - Oct 30
195 7:40 pm 10:20 pm Oct 31 - Oct 31
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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 $167
only $222
Destination

Oakland
$167
Airlines Airline reviews

115 travelers who booked a flight from Chicago to Oakland rated their chosen airlines with an average of 5.1.

Overall
5.4
Boarding
5.7
Crew
6.3
Comfort
5.0
Food
3.8
Entertainment
3.5