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: Wed Sep 20 2017 Return: Tue Sep 26 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Sat Sep 9 2017 Return: Sat Sep 16 2017 Trip spans 8 days
Delta
Delta
OAK
MDW
11h 03m
2 stops
MDW
OAK
10h 21m
2 stops
Depart: Thu Oct 12 2017 Return: Sat Oct 14 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Fri Sep 8 2017 Return: Wed Sep 13 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Thu Nov 16 2017 Return: Sun Nov 19 2017 Trip spans 4 days
Alaska Airlines
Alaska Airlines
OAK
ORD
7h 07m
1 stop
ORD
OAK
7h 31m
1 stop
Depart: Wed Aug 23 2017 Return: Tue Aug 29 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Sat Aug 19 2017 Return: Wed Aug 23 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Tue Sep 12 2017 Return: Sat Sep 16 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Wed Oct 4 2017 Return: Tue Oct 10 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Fri Oct 13 2017 Return: Tue Oct 17 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Wed Nov 29 2017 Return: Tue Dec 5 2017 Trip spans 7 days
Delta
Delta
OAK
MDW
8h 44m
2 stops
MDW
OAK
8h 59m
2 stops
Depart: Fri Nov 3 2017 Return: Mon Nov 6 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Mon Dec 4 2017 Return: Wed Dec 13 2017 Trip spans 10 days
Delta
Delta
OAK
MDW
12h 12m
2 stops
MDW
OAK
8h 59m
2 stops
Depart: Tue Aug 1 2017 Return: Tue Aug 8 2017 Trip spans 8 days
Delta
Delta
OAK
MDW
11h 12m
2 stops
MDW
OAK
8h 02m
1 stop
Depart: Wed Nov 1 2017 Return: Mon Nov 6 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 12m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Wed Jul 26 2017 Return: Tue Aug 1 2017 Trip spans 7 days
Delta
Delta
OAK
MDW
11h 07m
2 stops
MDW
OAK
10h 18m
2 stops
Depart: Sat Aug 19 2017 Return: Wed Aug 23 2017 Trip spans 5 days
Delta
Delta
OAK
MDW
8h 45m
2 stops
MDW
OAK
9h 34m
2 stops
Depart: Sat Jul 29 2017 Return: Tue Aug 1 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Thu Sep 14 2017 Return: Mon Sep 18 2017 Trip spans 5 days
Delta
Delta
OAK
MDW
11h 08m
2 stops
MDW
OAK
12h 02m
2 stops
Depart: Fri Dec 1 2017 Return: Mon Dec 4 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
OAK
ORD
15h 49m
1 stop
ORD
OAK
10h 14m
1 stop
Direct flights OAK to CHI on Southwest
Flight # Depart OAK Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
1307 5:50 am 11:55 am Aug 15 - Sep 1
1341 6:00 am 12:05 pm Jul 24 - Aug 14
3758 6:50 am 12:55 pm Aug 20 - Aug 27
4321 6:50 am 12:50 pm Jul 22 - Aug 12
4490 6:55 am 1:00 pm Aug 19 - Aug 26
4788 7:10 am 1:10 pm Jul 23 - Aug 13
1892 7:25 am 1:30 pm Aug 15 - Sep 29
1338 7:30 am 1:30 pm Jul 24 - Aug 14
4808 8:10 am 2:10 pm Jul 22 - Aug 12
2052 9:50 am 3:50 pm Jul 24 - Aug 14
4395 9:50 am 3:50 pm Aug 20 - Aug 27
5057 9:50 am 3:50 pm Jul 23 - Aug 13
585 11:50 am 5:50 pm Aug 15 - Sep 1
2508 12:15 pm 6:15 pm Aug 19 - Sep 23
4550 1:20 pm 7:20 pm Jul 22 - Aug 12
3794 1:30 pm 7:30 pm Jul 23 - Aug 13
2087 2:15 pm 8:15 pm Aug 19 - Aug 26
4923 2:40 pm 8:40 pm Aug 20 - Aug 27
1990 2:50 pm 8:50 pm Aug 15 - Sep 29
4401 3:10 pm 9:10 pm Jul 22 - Aug 12
4793 3:20 pm 9:20 pm Jul 23 - Aug 13
404 3:30 pm 9:30 pm Jul 24 - Aug 14
* 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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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

Oakland
$159
Destination

Chicago
only $159
only $282
Airlines Airline reviews

161 travelers who booked a flight from Oakland to Chicago rated their chosen airlines with an average of 5.3.

Overall
5.6
Boarding
6.3
Crew
6.4
Comfort
5.1
Food
3.6
Entertainment
3.4