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
The price shown for each flight will be the average for all passengers including any infants.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Oakland to Chicago

(Round-trip)
Depart: Sat Apr 29 2017 Return: Tue May 2 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 16m
nonstop
ORD
OAK
4h 36m
nonstop
Depart: Tue May 2 2017 Return: Thu May 4 2017 Trip spans 3 days
Major Airline
Major Airline
OAK
ORD
4h 16m
nonstop
ORD
OAK
4h 36m
nonstop
Depart: Wed May 3 2017 Return: Sat May 6 2017 Trip spans 4 days
Delta
Delta
OAK
MDW
9h 59m
2 stops
MDW
OAK
9h 45m
2 stops
Depart: Wed Mar 29 2017 Return: Tue May 2 2017 Trip spans 35 days
American Airlines
American Airlines
OAK
ORD
6h 28m
1 stop
ORD
OAK
9h 02m
1 stop
Depart: Wed May 3 2017 Return: Thu May 11 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 16m
nonstop
ORD
OAK
4h 36m
nonstop
Depart: Wed Aug 16 2017 Return: Wed Aug 23 2017 Trip spans 8 days
Major Airline
Major Airline
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 34m
nonstop
Depart: Sat Sep 9 2017 Return: Wed Sep 13 2017 Trip spans 5 days
Major Airline
Major Airline
OAK
ORD
4h 00m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Fri Apr 28 2017 Return: Tue May 2 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 16m
nonstop
ORD
OAK
4h 36m
nonstop
Depart: Thu Sep 21 2017 Return: Mon Sep 25 2017 Trip spans 5 days
Major Airline
Major Airline
OAK
ORD
4h 00m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Wed Sep 6 2017 Return: Wed Sep 13 2017 Trip spans 8 days
Delta
Delta
OAK
MDW
11h 03m
2 stops
MDW
OAK
10h 42m
2 stops
Depart: Sat Sep 9 2017 Return: Sun Sep 10 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 00m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Thu May 11 2017 Return: Sat May 13 2017 Trip spans 3 days
Major Airline
Major Airline
OAK
ORD
4h 16m
nonstop
ORD
OAK
4h 36m
nonstop
Depart: Tue Apr 25 2017 Return: Fri Apr 28 2017 Trip spans 4 days
Delta
Delta
OAK
MDW
8h 52m
2 stops
MDW
OAK
10h 55m
2 stops
Depart: Thu Jun 1 2017 Return: Tue Jun 6 2017 Trip spans 6 days
Major Airline
Major Airline
OAK
ORD
4h 15m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Fri Jun 9 2017 Return: Tue Jun 13 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 15m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Tue Mar 28 2017 Return: Sat Apr 29 2017 Trip spans 33 days
American Airlines
American Airlines
OAK
ORD
6h 28m
1 stop
ORD
OAK
7h 06m
1 stop
Depart: Sat Aug 26 2017 Return: Fri Sep 29 2017 Trip spans 35 days
Major Airline
Major Airline
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 35m
nonstop
Depart: Wed Apr 26 2017 Return: Mon May 1 2017 Trip spans 6 days
Delta
Delta
OAK
MDW
7h 56m
2 stops
MDW
OAK
9h 39m
2 stops
Depart: Mon Jul 17 2017 Return: Mon Aug 21 2017 Trip spans 36 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 34m
nonstop
Depart: Tue Aug 1 2017 Return: Thu Aug 10 2017 Trip spans 10 days
Spirit Airlines
Spirit Airlines
OAK
ORD
4h 10m
nonstop
ORD
OAK
4h 34m
nonstop
Direct flights OAK to CHI on Southwest
Flight # Depart OAK Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
1193 6:25 am 12:35 pm Mar 22 - Apr 24
1289 6:25 am 12:35 pm Apr 25 - Jun 2
6346 6:40 am 12:45 pm Mar 25 - Apr 22
4476 6:55 am 1:00 pm Apr 29 - Jun 3
4597 7:00 am 1:10 pm Apr 30 - May 28
3935 7:20 am 1:25 pm Mar 26 - Apr 23
1592 8:55 am 3:00 pm Apr 25 - May 8
4596 9:05 am 3:10 pm Apr 30 - May 28
2631 1:55 pm 8:00 pm Apr 29 - Apr 29
2515 2:25 pm 8:30 pm Apr 30 - May 28
594 2:40 pm 8:45 pm Apr 25 - Apr 25
594 2:40 pm 8:45 pm Apr 26 - May 26
1443 2:50 pm 8:55 pm Mar 22 - Apr 24
4826 2:55 pm 9:00 pm Mar 25 - Apr 22
5771 3:10 pm 9:15 pm Mar 26 - Apr 23
* 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.

We compile tonnes of data for you
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.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Oakland
$205
Destination

Chicago
only $205
only $262
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