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
Students
under 26
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: Tue Jan 31 2017 Return: Tue Mar 14 2017 Trip spans 42 days
Spirit Airlines
Spirit Airlines
ORD
OAK
17h 48m
1 stop
OAK
ORD
13h 01m
1 stop
Depart: Thu Apr 27 2017 Return: Tue May 2 2017 Trip spans 6 days
Major Airline
Major Airline
ORD
OAK
4h 33m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Tue May 23 2017 Return: Sat May 27 2017 Trip spans 5 days
Delta
Delta
MDW
OAK
13h 00m
2 stops
OAK
MDW
7h 33m
1 stop
Depart: Tue Apr 11 2017 Return: Tue Apr 25 2017 Trip spans 15 days
Alaska Airlines
Alaska Airlines
ORD
OAK
9h 54m
1 stop
OAK
ORD
6h 57m
1 stop
Depart: Tue Mar 7 2017 Return: Wed Mar 22 2017 Trip spans 15 days
Spirit Airlines
Spirit Airlines
ORD
OAK
17h 35m
1 stop
OAK
ORD
13h 01m
1 stop
Depart: Tue May 2 2017 Return: Sat May 6 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
OAK
4h 33m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Wed May 3 2017 Return: Tue May 9 2017 Trip spans 7 days
Major Airline
Major Airline
ORD
OAK
4h 33m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Sat Jun 3 2017 Return: Sat Jun 10 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 33m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Thu Feb 9 2017 Return: Mon Feb 13 2017 Trip spans 5 days
Delta
Delta
MDW
OAK
12h 57m
2 stops
OAK
MDW
13h 08m
2 stops
Depart: Wed May 17 2017 Return: Mon May 22 2017 Trip spans 6 days
Major Airline
Major Airline
ORD
OAK
4h 33m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Sat Apr 29 2017 Return: Tue May 2 2017 Trip spans 4 days
Delta
Delta
MDW
OAK
13h 25m
2 stops
OAK
MDW
13h 16m
2 stops
Depart: Wed May 24 2017 Return: Mon May 29 2017 Trip spans 6 days
Major Airline
Major Airline
ORD
OAK
4h 33m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Thu May 18 2017 Return: Sun May 21 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 33m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Tue May 2 2017 Return: Fri May 5 2017 Trip spans 4 days
Delta
Delta
MDW
OAK
10h 35m
2 stops
OAK
MDW
12h 35m
2 stops
Depart: Fri Jun 9 2017 Return: Tue Jun 13 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
OAK
4h 33m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Fri Jan 27 2017 Return: Tue Jan 31 2017 Trip spans 5 days
Delta
Delta
MDW
OAK
9h 23m
2 stops
OAK
MDW
10h 30m
2 stops
Depart: Thu Apr 20 2017 Return: Sat Apr 22 2017 Trip spans 3 days
Delta
Delta
MDW
OAK
10h 45m
2 stops
OAK
MDW
8h 42m
2 stops
Depart: Fri Apr 28 2017 Return: Sun Apr 30 2017 Trip spans 3 days
Major Airline
Major Airline
ORD
OAK
4h 33m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Thu Feb 16 2017 Return: Tue Feb 21 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
OAK
10h 21m
1 stop
OAK
ORD
10h 44m
1 stop
Depart: Wed Feb 8 2017 Return: Sat Feb 11 2017 Trip spans 4 days
Delta
Delta
MDW
OAK
12h 27m
2 stops
OAK
MDW
9h 44m
2 stops
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
1889 8:40 am 11:25 am Feb 13 - Feb 20
1889 8:40 am 11:25 am Feb 8 - Feb 10
1889 8:40 am 11:25 am Feb 1 - Feb 7
1889 8:40 am 11:25 am Jan 30 - Jan 31
1889 8:40 am 11:25 am Feb 21 - Mar 3
1889 8:40 am 11:25 am Feb 14 - Feb 14
2503 8:45 am 11:30 am Jan 21 - Mar 4
2739 9:05 am 11:50 am Feb 12 - Feb 12
2739 9:05 am 11:50 am Feb 19 - Mar 5
2739 9:05 am 11:50 am Jan 29 - Jan 29
5801 9:05 am 11:50 am Feb 5 - Feb 5
4532 7:45 pm 10:30 pm Feb 15 - Mar 8
4532 7:45 pm 10:30 pm Jan 19 - Feb 13
4209 8:15 pm 10:55 pm Feb 12 - Mar 5
4209 8:15 pm 10:55 pm Jan 22 - Jan 29
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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 $213
only $268
Destination

Oakland
$213
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