Find Deals on 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
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 Oakland to Chicago

(Round-trip)
Depart: Tue Jan 10 2017 Return: Tue Jan 17 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
OAK
ORD
5h 56m
1 stop
ORD
OAK
10h 08m
1 stop
Depart: Wed May 10 2017 Return: Mon May 15 2017 Trip spans 6 days
Major Airline
Major Airline
OAK
ORD
4h 14m
nonstop
ORD
OAK
4h 33m
nonstop
Depart: Sat Feb 4 2017 Return: Sat Mar 4 2017 Trip spans 29 days
Delta
Delta
OAK
ORD
6h 34m
1 stop
ORD
OAK
9h 30m
1 stop
Depart: Sat Jan 21 2017 Return: Sat Jan 28 2017 Trip spans 8 days
American Airlines
American Airlines
OAK
ORD
6h 22m
1 stop
ORD
OAK
6h 47m
1 stop
Depart: Fri Jan 20 2017 Return: Sun Jan 22 2017 Trip spans 3 days
Southwest
Southwest
OAK
MDW
4h 05m
nonstop
MDW
OAK
4h 45m
nonstop
Depart: Thu May 4 2017 Return: Wed May 10 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 14m
nonstop
ORD
OAK
4h 33m
nonstop
Depart: Tue Feb 14 2017 Return: Tue Feb 28 2017 Trip spans 15 days
Delta
Delta
OAK
ORD
7h 40m
1 stop
ORD
OAK
6h 24m
1 stop
Depart: Thu Apr 27 2017 Return: Sun Apr 30 2017 Trip spans 4 days
Major Airline
Major Airline
OAK
ORD
4h 14m
nonstop
ORD
OAK
4h 33m
nonstop
Depart: Wed Feb 1 2017 Return: Fri Feb 3 2017 Trip spans 3 days
American Airlines
American Airlines
OAK
ORD
6h 22m
1 stop
ORD
OAK
7h 02m
1 stop
Depart: Wed Mar 1 2017 Return: Sat Mar 4 2017 Trip spans 4 days
Delta
Delta
OAK
ORD
7h 22m
1 stop
ORD
OAK
6h 47m
1 stop
Depart: Wed Dec 14 2016 Return: Tue Jan 10 2017 Trip spans 28 days
Spirit Airlines
Spirit Airlines
OAK
ORD
5h 56m
1 stop
ORD
OAK
10h 29m
1 stop
Depart: Tue Mar 21 2017 Return: Tue Mar 28 2017 Trip spans 8 days
Delta
Delta
OAK
ORD
5h 51m
1 stop
ORD
OAK
6h 07m
1 stop
Depart: Mon Feb 6 2017 Return: Mon Feb 13 2017 Trip spans 8 days
Southwest
Southwest
OAK
MDW
4h 05m
nonstop
MDW
OAK
4h 45m
nonstop
Depart: Thu Apr 27 2017 Return: Sun Apr 30 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 14m
nonstop
ORD
OAK
4h 33m
nonstop
Depart: Tue Feb 7 2017 Return: Fri Feb 10 2017 Trip spans 4 days
Southwest
Southwest
OAK
MDW
4h 05m
nonstop
MDW
OAK
4h 45m
nonstop
Depart: Wed Mar 1 2017 Return: Tue Mar 7 2017 Trip spans 7 days
Delta
Delta
OAK
MDW
9h 14m
2 stops
MDW
OAK
12h 06m
2 stops
Depart: Wed Mar 8 2017 Return: Wed Mar 15 2017 Trip spans 7 days
Major Airline
Major Airline
OAK
ORD
7h 28m
1 stop
ORD
OAK
6h 07m
1 stop
Depart: Tue Apr 25 2017 Return: Tue May 2 2017 Trip spans 8 days
Delta
Delta
OAK
MDW
11h 05m
2 stops
MDW
OAK
10h 35m
2 stops
Depart: Wed Mar 1 2017 Return: Wed Mar 15 2017 Trip spans 14 days
Southwest
Southwest
OAK
MDW
4h 10m
nonstop
MDW
OAK
4h 35m
nonstop
Depart: Tue May 30 2017 Return: Tue Jun 6 2017 Trip spans 8 days
Major Airline
Major Airline
OAK
ORD
4h 14m
nonstop
ORD
OAK
4h 33m
nonstop
Select an airline:  Southwest
Direct flights OAK to CHI on Southwest
Flight # Depart OAK Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
3269 5:45 am 11:55 am Dec 21 - Jan 2
1833 5:55 am 12:05 pm Jan 5 - Mar 8
3006 6:10 am 12:25 pm Dec 24 - Dec 24
3006 6:10 am 12:25 pm Dec 25 - Dec 25
695 6:10 am 12:25 pm Dec 31 - Dec 31
695 6:10 am 12:25 pm Jan 1 - Jan 4
695 6:10 am 12:25 pm Dec 4 - Dec 20
6380 6:15 am 12:30 pm Dec 17 - Dec 17
2130 6:20 am 12:30 pm Jan 7 - Mar 4
4189 7:10 am 1:20 pm Jan 8 - Jan 29
2099 8:30 am 2:30 pm Dec 21 - Jan 2
3262 8:35 am 2:35 pm Dec 4 - Dec 18
3262 8:35 am 2:35 pm Jan 3 - Jan 4
3262 8:35 am 2:35 pm Jan 1 - Jan 1
3262 8:35 am 2:35 pm Dec 5 - Dec 20
3347 8:35 am 2:35 pm Dec 25 - Dec 25
288 9:25 am 3:30 pm Dec 24 - Dec 24
2365 1:40 pm 7:45 pm Dec 31 - Dec 31
294 1:40 pm 7:45 pm Dec 24 - Dec 24
4192 1:45 pm 7:50 pm Dec 21 - Jan 2
1378 2:00 pm 8:05 pm Dec 17 - Dec 17
617 2:20 pm 8:25 pm Jan 5 - Jan 5
822 2:20 pm 8:25 pm Jan 6 - Jan 13
2167 3:00 pm 9:05 pm Dec 4 - Dec 20
2167 3:00 pm 9:05 pm Jan 1 - Jan 4
2877 3:00 pm 9:05 pm Dec 25 - Dec 25
3639 3:00 pm 9:05 pm Jan 8 - Jan 29
2035 3:20 pm 9:25 pm Dec 21 - Jan 2
1011 6:45 pm 12:50 am Dec 17 - Dec 17
* 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

Oakland
$184
Destination

Chicago
only $184
only $272
Airlines Airline reviews

131 travelers who booked a flight from Oakland to Chicago rated their chosen airlines with an average of 5.4.

Overall
5.7
Boarding
6.4
Crew
6.4
Comfort
5.1
Food
3.5
Entertainment
3.3