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: Sat Apr 29 2017 Return: Wed May 3 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
OAK
4h 33m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Wed Jan 11 2017 Return: Sat Jan 14 2017 Trip spans 4 days
Delta
Delta
ORD
OAK
6h 40m
1 stop
OAK
ORD
5h 56m
1 stop
Depart: Fri May 5 2017 Return: Sun May 7 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 33m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Fri Jan 27 2017 Return: Wed Feb 1 2017 Trip spans 6 days
American Airlines
American Airlines
ORD
OAK
7h 02m
1 stop
OAK
ORD
8h 20m
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: Sat Feb 25 2017 Return: Sat Mar 4 2017 Trip spans 8 days
Alaska Airlines
Alaska Airlines
ORD
OAK
16h 43m
1 stop
OAK
ORD
7h 28m
1 stop
Depart: Sat May 13 2017 Return: Mon May 15 2017 Trip spans 3 days
Major Airline
Major Airline
ORD
OAK
4h 33m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Sat Jan 28 2017 Return: Wed Feb 1 2017 Trip spans 5 days
Delta
Delta
ORD
OAK
6h 33m
1 stop
OAK
ORD
7h 40m
1 stop
Depart: Sat Dec 10 2016 Return: Tue Dec 13 2016 Trip spans 4 days
Major Airline
Major Airline
ORD
OAK
5h 39m
nonstop
OAK
ORD
1h 39m
nonstop
Depart: Sat Feb 4 2017 Return: Wed Feb 8 2017 Trip spans 5 days
Delta
Delta
ORD
OAK
9h 43m
1 stop
OAK
ORD
7h 40m
1 stop
Depart: Wed Mar 29 2017 Return: Wed Apr 5 2017 Trip spans 8 days
Delta
Delta
ORD
OAK
6h 07m
1 stop
OAK
ORD
5h 49m
1 stop
Depart: Wed Dec 7 2016 Return: Wed Dec 14 2016 Trip spans 8 days
Major Airline
Major Airline
ORD
OAK
5h 39m
nonstop
OAK
ORD
1h 39m
nonstop
Depart: Tue Jun 6 2017 Return: Tue Jun 13 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 33m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Tue Feb 28 2017 Return: Tue Mar 7 2017 Trip spans 8 days
Delta
Delta
ORD
OAK
6h 24m
1 stop
OAK
ORD
13h 52m
2 stops
Depart: Wed Dec 7 2016 Return: Tue Dec 13 2016 Trip spans 7 days
Major Airline
Major Airline
ORD
OAK
5h 39m
nonstop
OAK
ORD
1h 39m
nonstop
Depart: Tue Feb 28 2017 Return: Tue Mar 7 2017 Trip spans 8 days
Delta
Delta
MDW
OAK
12h 50m
2 stops
OAK
MDW
13h 25m
2 stops
Depart: Wed May 10 2017 Return: Sat May 20 2017 Trip spans 11 days
Spirit Airlines
Spirit Airlines
ORD
OAK
4h 33m
nonstop
OAK
ORD
4h 14m
nonstop
Depart: Sun Apr 9 2017 Return: Tue Apr 25 2017 Trip spans 17 days
Southwest
Southwest
MDW
OAK
4h 30m
nonstop
OAK
MDW
4h 05m
nonstop
Depart: Sat Mar 11 2017 Return: Wed Mar 15 2017 Trip spans 4 days
Delta
Delta
ORD
OAK
6h 07m
1 stop
OAK
ORD
5h 51m
1 stop
Depart: Mon Feb 13 2017 Return: Fri Feb 17 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
OAK
12h 00m
2 stops
OAK
ORD
10h 38m
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
6003 7:55 am 10:40 am Dec 21 - Dec 21
6003 7:55 am 10:40 am Dec 22 - Jan 2
2427 8:10 am 11:00 am Jan 1 - Jan 4
2427 8:10 am 11:00 am Dec 1 - Dec 20
3299 8:10 am 11:00 am Dec 25 - Dec 25
1889 8:40 am 11:25 am Jan 5 - Jan 13
2503 8:45 am 11:30 am Jan 7 - Mar 4
2554 8:50 am 11:40 am Dec 24 - Dec 24
5966 8:50 am 11:40 am Dec 3 - Dec 10
951 8:50 am 11:40 am Dec 31 - Dec 31
2739 9:05 am 11:50 am Jan 8 - Jan 8
5500 9:20 am 12:10 pm Dec 17 - Dec 17
1397 12:10 pm 2:55 pm Dec 11 - Dec 20
1397 12:10 pm 2:55 pm Jan 1 - Jan 4
1397 12:10 pm 2:55 pm Dec 4 - Dec 9
5962 12:35 pm 3:20 pm Dec 21 - Jan 2
2509 3:50 pm 6:35 pm Dec 17 - Dec 17
2587 4:00 pm 6:45 pm Dec 24 - Dec 24
6001 4:00 pm 6:45 pm Dec 10 - Dec 10
836 4:00 pm 6:45 pm Dec 31 - Dec 31
4550 5:05 pm 7:50 pm Dec 21 - Jan 2
852 6:35 pm 9:20 pm Dec 24 - Dec 24
5115 6:40 pm 9:25 pm Dec 3 - Dec 10
489 7:00 pm 9:40 pm Dec 17 - Dec 17
2472 7:25 pm 10:10 pm Dec 25 - Dec 25
3665 7:25 pm 10:10 pm Dec 1 - Dec 20
3665 7:25 pm 10:10 pm Jan 1 - Jan 4
4532 7:45 pm 10:30 pm Jan 5 - Feb 13
4179 8:10 pm 11:00 pm Dec 21 - Jan 2
4209 8:15 pm 10:55 pm Jan 8 - Jan 29
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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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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 $227
only $272
Destination

Oakland
$227
Airlines Airline reviews

134 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