Find Cheap Flights from Oakland to Chicago (OAK - CHI)

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 Oakland to Chicago

(Round-trip)
Depart: Tue Oct 24 2017 Return: Tue Oct 31 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Fri Dec 8 2017 Return: Mon Dec 11 2017 Trip spans 4 days
Multiple Airlines
Multiple Airlines
OAK
ORD
20h 15m
1 stop
ORD
OAK
15h 57m
1 stop
Depart: Wed Oct 25 2017 Return: Tue Oct 31 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Wed Oct 25 2017 Return: Tue Oct 31 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Tue Oct 24 2017 Return: Sat Nov 4 2017 Trip spans 12 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Wed Oct 25 2017 Return: Wed Nov 1 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Sat Oct 28 2017 Return: Sat Nov 4 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Tue Oct 31 2017 Return: Tue Nov 7 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Wed Nov 1 2017 Return: Wed Nov 8 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Thu Nov 16 2017 Return: Mon Nov 27 2017 Trip spans 12 days
Multiple Airlines
Multiple Airlines
OAK
ORD
10h 33m
1 stop
ORD
OAK
15h 42m
1 stop
Depart: Sat Nov 4 2017 Return: Tue Nov 7 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Thu Oct 26 2017 Return: Sun Nov 19 2017 Trip spans 25 days
Multiple Airlines
Multiple Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
15h 42m
1 stop
Depart: Tue Nov 7 2017 Return: Wed Nov 8 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Thu Nov 16 2017 Return: Mon Nov 20 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
OAK
ORD
6h 08m
1 stop
ORD
OAK
15h 42m
1 stop
Depart: Tue Oct 24 2017 Return: Wed Nov 1 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Wed Oct 25 2017 Return: Wed Nov 1 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Tue Oct 31 2017 Return: Wed Nov 8 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Tue Oct 24 2017 Return: Thu Oct 26 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Wed Oct 25 2017 Return: Thu Oct 26 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Wed Nov 1 2017 Return: Thu Nov 2 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Direct flights OAK to CHI on Southwest
Flight # Depart OAK Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
5827 5:15 am 11:15 am Nov 17 - Nov 22
5827 5:15 am 11:15 am Nov 26 - Nov 27
177 5:40 am 11:45 am Nov 6 - Nov 16
177 5:40 am 11:45 am Nov 20 - Nov 20
396 5:40 am 11:45 am Nov 24 - Nov 24
366 5:45 am 11:50 am Nov 23 - Nov 23
2696 5:50 am 11:55 am Nov 18 - Nov 18
2696 6:00 am 12:05 pm Nov 25 - Nov 25
1125 6:15 am 12:25 pm Oct 9 - Nov 3
2753 6:45 am 12:50 pm Oct 8 - Oct 29
3428 6:45 am 12:50 pm Oct 7 - Oct 28
3986 6:45 am 12:50 pm Nov 11 - Nov 11
2491 6:50 am 12:55 pm Nov 4 - Nov 4
4084 6:50 am 12:55 pm Nov 5 - Nov 19
5016 7:50 am 1:50 pm Nov 26 - Nov 27
5016 7:50 am 1:50 pm Nov 17 - Nov 22
1795 9:20 am 3:25 pm Oct 9 - Oct 30
1795 9:20 am 3:25 pm Nov 1 - Nov 3
1795 9:20 am 3:25 pm Oct 31 - Oct 31
5269 9:55 am 4:00 pm Oct 22 - Oct 29
1132 10:00 am 4:00 pm Nov 4 - Nov 4
2014 10:05 am 4:05 pm Nov 18 - Nov 18
426 10:05 am 4:05 pm Nov 25 - Nov 25
6094 11:40 am 5:40 pm Nov 5 - Nov 19
625 11:45 am 5:45 pm Nov 20 - Nov 20
625 11:45 am 5:45 pm Nov 24 - Nov 24
625 11:45 am 5:45 pm Nov 6 - Nov 16
4216 12:00 pm 6:00 pm Oct 7 - Oct 28
3392 12:15 pm 6:15 pm Nov 23 - Nov 23
1039 1:20 pm 7:20 pm Nov 4 - Nov 4
1687 1:25 pm 7:25 pm Oct 9 - Oct 30
1687 1:25 pm 7:25 pm Nov 1 - Nov 3
4761 2:05 pm 8:05 pm Nov 11 - Nov 11
4501 2:10 pm 8:15 pm Oct 7 - Oct 28
6373 2:30 pm 8:35 pm Oct 8 - Oct 29
5736 2:50 pm 8:55 pm Nov 20 - Nov 24
5736 2:50 pm 8:55 pm Nov 6 - Nov 16
4593 2:55 pm 8:55 pm Nov 5 - Nov 19
4918 3:00 pm 9:05 pm Oct 9 - Nov 3
4726 3:15 pm 9:15 pm Nov 18 - Nov 18
6683 3:20 pm 9:20 pm Nov 25 - Nov 25
6683 3:20 pm 9:20 pm Nov 17 - Nov 22
6683 3:20 pm 9:20 pm Nov 26 - Nov 27
3815 7:20 pm 1:25 am Nov 17 - Nov 22
3815 7:20 pm 1:25 am Nov 26 - Nov 27
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

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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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

Oakland
$131
Destination

Chicago
$131
Airlines Airline reviews

184 travelers who booked a flight from Oakland to Chicago rated their chosen airlines with an average of 5.5.

Overall
5.8
Boarding
6.5
Crew
6.6
Comfort
5.3
Food
3.7
Entertainment
3.5