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: Wed May 3 2017 Return: Wed May 10 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 16m
nonstop
Depart: Fri Apr 28 2017 Return: Mon May 1 2017 Trip spans 4 days
Major Airline
Major Airline
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 16m
nonstop
Depart: Wed Mar 1 2017 Return: Thu Mar 2 2017 Trip spans 2 days
Delta
Delta
MDW
OAK
9h 05m
2 stops
OAK
MDW
14h 28m
2 stops
Depart: Wed May 10 2017 Return: Tue May 23 2017 Trip spans 14 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 16m
nonstop
Depart: Sat Apr 29 2017 Return: Wed May 3 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 16m
nonstop
Depart: Thu Apr 27 2017 Return: Sun Apr 30 2017 Trip spans 4 days
Major Airline
Major Airline
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 16m
nonstop
Depart: Wed Mar 1 2017 Return: Wed Mar 15 2017 Trip spans 14 days
Spirit Airlines
Spirit Airlines
ORD
OAK
10h 21m
1 stop
OAK
ORD
6h 50m
1 stop
Depart: Thu Mar 2 2017 Return: Wed Mar 8 2017 Trip spans 7 days
Delta
Delta
MDW
OAK
9h 39m
2 stops
OAK
MDW
10h 32m
2 stops
Depart: Wed Mar 22 2017 Return: Wed Mar 29 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
OAK
10h 05m
1 stop
OAK
ORD
5h 55m
1 stop
Depart: Wed Apr 19 2017 Return: Tue Apr 25 2017 Trip spans 7 days
Delta
Delta
MDW
OAK
9h 34m
2 stops
OAK
MDW
11h 11m
2 stops
Depart: Tue Mar 28 2017 Return: Wed Mar 29 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
OAK
10h 05m
1 stop
OAK
ORD
5h 55m
1 stop
Depart: Tue Jul 18 2017 Return: Wed Jul 26 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
OAK
4h 34m
nonstop
OAK
ORD
4h 10m
nonstop
Depart: Wed Apr 26 2017 Return: Tue May 2 2017 Trip spans 7 days
Delta
Delta
MDW
OAK
9h 34m
2 stops
OAK
MDW
8h 49m
2 stops
Depart: Mon May 1 2017 Return: Sat May 6 2017 Trip spans 6 days
Delta
Delta
MDW
OAK
10h 45m
2 stops
OAK
MDW
8h 40m
2 stops
Depart: Thu Mar 2 2017 Return: Mon Mar 6 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
OAK
5h 39m
nonstop
OAK
ORD
1h 39m
nonstop
Depart: Wed May 10 2017 Return: Tue May 16 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 16m
nonstop
Depart: Sat May 13 2017 Return: Tue May 23 2017 Trip spans 11 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 36m
nonstop
OAK
ORD
4h 16m
nonstop
Depart: Tue Aug 22 2017 Return: Sat Aug 26 2017 Trip spans 5 days
Delta
Delta
MDW
OAK
7h 41m
1 stop
OAK
MDW
8h 16m
1 stop
Depart: Tue Aug 22 2017 Return: Sat Aug 26 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 33m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Mon Jul 10 2017 Return: Mon Jul 17 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
OAK
4h 34m
nonstop
OAK
ORD
4h 10m
nonstop
Select an airline:  Southwest
Direct flights CHI to OAK on Southwest
Flight # Depart MDW Arrive OAK Sun Mon Tue Wed Thu Fri Sat Valid Between
4784 8:30 am 11:05 am Mar 13 - Apr 24
4784 8:30 am 11:05 am Mar 9 - Mar 10
1889 8:40 am 11:25 am Mar 6 - Mar 8
1889 8:40 am 11:25 am Feb 16 - Mar 3
2627 8:40 am 11:15 am Mar 18 - Apr 22
2627 8:40 am 11:15 am Mar 11 - Mar 11
2503 8:45 am 11:30 am Feb 18 - Mar 4
2739 9:05 am 11:50 am Feb 19 - Mar 5
425 9:05 am 11:35 am Mar 19 - Mar 19
425 9:05 am 11:35 am Mar 12 - Mar 12
425 9:05 am 11:35 am Mar 26 - Apr 23
1798 7:45 pm 10:20 pm Mar 9 - Mar 9
4532 7:45 pm 10:30 pm Feb 16 - Mar 8
2215 7:55 pm 10:30 pm Mar 11 - Mar 11
2215 7:55 pm 10:30 pm Mar 18 - Apr 22
2375 8:10 pm 10:45 pm Mar 10 - Mar 10
2375 8:10 pm 10:45 pm Mar 13 - Apr 24
4209 8:15 pm 10:55 pm Feb 19 - Mar 5
3689 8:35 pm 11:05 pm Mar 12 - Apr 23
* 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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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 $149
only $272
Destination

Oakland
$149
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