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 May 16 2017 Return: Wed May 17 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 16m
nonstop
ORD
OAK
4h 36m
nonstop
Depart: Mon May 15 2017 Return: Tue May 16 2017 Trip spans 2 days
Major Airline
Major Airline
OAK
ORD
4h 16m
nonstop
ORD
OAK
4h 36m
nonstop
Depart: Tue Jun 6 2017 Return: Wed Jun 7 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 15m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Tue May 9 2017 Return: Wed May 10 2017 Trip spans 2 days
Delta
Delta
OAK
MDW
12h 45m
2 stops
MDW
OAK
11h 59m
2 stops
Depart: Fri Apr 28 2017 Return: Mon May 1 2017 Trip spans 4 days
American Airlines
American Airlines
OAK
ORD
8h 14m
1 stop
ORD
OAK
7h 06m
1 stop
Depart: Wed Aug 9 2017 Return: Mon Aug 14 2017 Trip spans 6 days
Major Airline
Major Airline
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Thu Jun 1 2017 Return: Sun Jun 4 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 15m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Thu Aug 24 2017 Return: Sun Aug 27 2017 Trip spans 4 days
Major Airline
Major Airline
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 34m
nonstop
Depart: Tue Jul 11 2017 Return: Tue Jul 18 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Sat Aug 26 2017 Return: Thu Aug 31 2017 Trip spans 6 days
Major Airline
Major Airline
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Thu May 11 2017 Return: Tue May 16 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 16m
nonstop
ORD
OAK
4h 36m
nonstop
Depart: Fri Sep 8 2017 Return: Sun Sep 10 2017 Trip spans 3 days
Major Airline
Major Airline
OAK
ORD
4h 00m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Mon Jul 3 2017 Return: Fri Jul 7 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Tue Sep 19 2017 Return: Sun Sep 24 2017 Trip spans 6 days
Major Airline
Major Airline
OAK
ORD
4h 00m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Sat Jun 3 2017 Return: Wed Jun 7 2017 Trip spans 5 days
Delta
Delta
OAK
MDW
13h 39m
2 stops
MDW
OAK
9h 15m
2 stops
Depart: Tue Oct 10 2017 Return: Sat Oct 14 2017 Trip spans 5 days
Major Airline
Major Airline
OAK
ORD
4h 00m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Thu Jun 8 2017 Return: Mon Jun 12 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 15m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Tue Oct 10 2017 Return: Tue Oct 17 2017 Trip spans 8 days
Delta
Delta
OAK
MDW
13h 47m
2 stops
MDW
OAK
13h 28m
2 stops
Depart: Fri Oct 13 2017 Return: Sun Oct 15 2017 Trip spans 3 days
Major Airline
Major Airline
OAK
ORD
4h 00m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Fri Apr 28 2017 Return: Mon May 1 2017 Trip spans 4 days
American Airlines
American Airlines
OAK
ORD
6h 24m
1 stop
ORD
OAK
6h 54m
1 stop
Direct flights OAK to CHI on Southwest
Flight # Depart OAK Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
1289 6:25 am 12:35 pm Apr 25 - Jun 2
4476 6:55 am 1:00 pm Apr 29 - Jun 3
4597 7:00 am 1:10 pm Apr 30 - May 28
1592 8:55 am 3:00 pm May 30 - Jun 2
1592 8:55 am 3:00 pm Apr 25 - May 8
1592 8:55 am 3:00 pm May 9 - May 26
1592 8:55 am 3:00 pm May 29 - May 29
4596 9:05 am 3:10 pm Apr 30 - May 28
2631 1:55 pm 8:00 pm May 13 - Jun 3
2631 1:55 pm 8:00 pm May 6 - May 6
2515 2:25 pm 8:30 pm Apr 30 - May 28
1663 2:40 pm 8:45 pm May 29 - May 29
594 2:40 pm 8:45 pm May 30 - Jun 2
594 2:40 pm 8:45 pm Apr 26 - May 26
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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
$138
Destination

Chicago
only $138
only $349
Airlines Airline reviews

127 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
6.3
Comfort
5.0
Food
3.4
Entertainment
3.2