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 Aug 16 2017 Return: Thu Aug 17 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Wed Aug 30 2017 Return: Thu Sep 7 2017 Trip spans 9 days
Major Airline
Major Airline
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Mon Oct 23 2017 Return: Mon Oct 30 2017 Trip spans 8 days
Southwest
Southwest
OAK
MDW
4h 05m
nonstop
MDW
OAK
4h 40m
nonstop
Depart: Thu Sep 7 2017 Return: Tue Sep 12 2017 Trip spans 6 days
Delta
Delta
OAK
MDW
14h 15m
2 stops
MDW
OAK
10h 42m
2 stops
Depart: Wed Aug 23 2017 Return: Sat Aug 26 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Thu Sep 7 2017 Return: Mon Sep 11 2017 Trip spans 5 days
Major Airline
Major Airline
OAK
ORD
4h 11m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Tue Sep 5 2017 Return: Wed Sep 6 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Tue Jun 6 2017 Return: Wed Jun 7 2017 Trip spans 2 days
Major Airline
Major Airline
OAK
ORD
4h 15m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Wed Aug 2 2017 Return: Wed Aug 9 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Thu Oct 26 2017 Return: Fri Oct 27 2017 Trip spans 2 days
Major Airline
Major Airline
OAK
ORD
4h 11m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Tue Jun 13 2017 Return: Tue Jun 20 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 15m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Tue Jul 18 2017 Return: Wed Aug 9 2017 Trip spans 23 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Sat Sep 9 2017 Return: Wed Sep 13 2017 Trip spans 5 days
Delta
Delta
OAK
MDW
12h 41m
2 stops
MDW
OAK
9h 25m
2 stops
Depart: Sat Jun 3 2017 Return: Fri Jul 21 2017 Trip spans 49 days
Major Airline
Major Airline
OAK
ORD
4h 15m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Thu Oct 5 2017 Return: Sun Oct 8 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 11m
nonstop
ORD
OAK
4h 38m
nonstop
Depart: Tue Sep 12 2017 Return: Mon Sep 18 2017 Trip spans 7 days
Delta
Delta
OAK
MDW
12h 05m
2 stops
MDW
OAK
10h 53m
2 stops
Depart: Sat May 27 2017 Return: Fri Jun 2 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 15m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Wed Aug 16 2017 Return: Tue Aug 22 2017 Trip spans 7 days
Delta
Delta
OAK
MDW
8h 51m
1 stop
MDW
OAK
10h 42m
2 stops
Depart: Sat Sep 2 2017 Return: Wed Sep 6 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Sat May 27 2017 Return: Sun May 28 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 15m
nonstop
ORD
OAK
4h 35m
nonstop
Direct flights OAK to CHI on Southwest
Flight # Depart OAK Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
5222 5:55 am 12:00 pm Jul 3 - Jul 3
1341 6:00 am 12:05 pm Jun 5 - Jun 30
1289 6:25 am 12:35 pm May 22 - Jun 2
4321 6:50 am 12:50 pm Jun 10 - Aug 12
4476 6:55 am 1:00 pm May 20 - Jun 3
4788 7:10 am 1:10 pm Jun 4 - Aug 13
1338 7:30 am 1:30 pm Jun 5 - Aug 14
4808 8:10 am 2:10 pm Jun 10 - Aug 12
1592 8:55 am 3:00 pm May 30 - Jun 2
2052 9:50 am 3:50 pm Jun 5 - Jun 30
4634 9:50 am 3:50 pm Jul 3 - Jul 3
5057 9:50 am 3:50 pm Jun 4 - Aug 13
4550 1:20 pm 7:20 pm Jun 10 - Jul 15
3794 1:30 pm 7:30 pm Jun 4 - Aug 13
2631 1:55 pm 8:00 pm May 20 - Jun 3
594 2:40 pm 8:45 pm May 30 - Jun 2
4401 3:10 pm 9:10 pm Jun 10 - Aug 12
4793 3:20 pm 9:20 pm Jun 4 - Aug 13
3853 3:25 pm 9:25 pm Jul 3 - Jul 3
404 3:30 pm 9:30 pm Jun 5 - Jun 30
* 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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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
$209
Destination

Chicago
only $209
only $270
Airlines Airline reviews

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

Overall
5.7
Boarding
6.3
Crew
6.4
Comfort
5.0
Food
3.5
Entertainment
3.4