Find Deals on Flights from Portland to Chicago (PWM - 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 Portland to Chicago

(Round-trip)
Depart: Wed Jun 1 2016 Return: Fri Jun 3 2016 Trip spans 3 days
JetBlue
JetBlue
PWM
ORD
8h 24m
1 stop
ORD
PWM
5h 13m
1 stop
Depart: Sat Jul 2 2016 Return: Tue Jul 5 2016 Trip spans 4 days
Major Airline
Major Airline
PWM
ORD
6h 33m
1 stop
ORD
PWM
4h 06m
1 stop
Depart: Thu Jun 9 2016 Return: Mon Jun 13 2016 Trip spans 5 days
Delta
Delta
PWM
MDW
10h 14m
2 stops
MDW
PWM
7h 02m
2 stops
Depart: Thu Aug 25 2016 Return: Sat Aug 27 2016 Trip spans 3 days
JetBlue
JetBlue
PWM
ORD
6h 12m
1 stop
ORD
PWM
5h 23m
1 stop
Depart: Mon Jul 18 2016 Return: Thu Jul 21 2016 Trip spans 4 days
United
United
PWM
ORD
5h 13m
1 stop
ORD
PWM
4h 24m
1 stop
Depart: Thu Oct 6 2016 Return: Tue Oct 11 2016 Trip spans 6 days
JetBlue
JetBlue
PWM
ORD
6h 17m
1 stop
ORD
PWM
5h 18m
1 stop
Depart: Sun Oct 9 2016 Return: Tue Oct 11 2016 Trip spans 3 days
JetBlue
JetBlue
PWM
ORD
6h 15m
1 stop
ORD
PWM
5h 28m
1 stop
Depart: Sat May 14 2016 Return: Sun May 29 2016 Trip spans 16 days
JetBlue
JetBlue
PWM
ORD
6h 53m
1 stop
ORD
PWM
5h 13m
1 stop
Depart: Fri Jun 10 2016 Return: Mon Jun 13 2016 Trip spans 4 days
Delta
Delta
PWM
MDW
8h 53m
2 stops
MDW
PWM
8h 12m
2 stops
Depart: Wed Sep 28 2016 Return: Mon Oct 3 2016 Trip spans 6 days
JetBlue
JetBlue
PWM
ORD
6h 15m
1 stop
ORD
PWM
5h 28m
1 stop
Depart: Sat May 28 2016 Return: Tue May 31 2016 Trip spans 4 days
Delta
Delta
PWM
MDW
6h 45m
1 stop
MDW
PWM
3h 54m
1 stop
Depart: Sat May 21 2016 Return: Mon May 23 2016 Trip spans 3 days
JetBlue
JetBlue
PWM
ORD
6h 53m
1 stop
ORD
PWM
5h 13m
1 stop
Depart: Wed Jul 13 2016 Return: Wed Jul 20 2016 Trip spans 8 days
Delta
Delta
PWM
MDW
4h 17m
1 stop
MDW
PWM
5h 39m
1 stop
Depart: Sat Jun 4 2016 Return: Sun Jun 5 2016 Trip spans 2 days
JetBlue
JetBlue
PWM
ORD
6h 23m
1 stop
ORD
PWM
5h 13m
1 stop
Depart: Fri Aug 5 2016 Return: Sun Aug 7 2016 Trip spans 3 days
Delta
Delta
PWM
MDW
7h 58m
1 stop
MDW
PWM
6h 58m
1 stop
Depart: Thu Jun 2 2016 Return: Sun Jun 5 2016 Trip spans 4 days
Major Airline
Major Airline
PWM
ORD
2h 52m
nonstop
ORD
PWM
2h 20m
nonstop
Depart: Sat Oct 8 2016 Return: Tue Oct 11 2016 Trip spans 4 days
JetBlue
JetBlue
PWM
ORD
6h 15m
1 stop
ORD
PWM
5h 28m
1 stop
Depart: Thu Sep 1 2016 Return: Sun Sep 4 2016 Trip spans 4 days
Delta
Delta
PWM
MDW
6h 40m
1 stop
MDW
PWM
3h 51m
1 stop
Depart: Tue Jul 26 2016 Return: Tue Aug 2 2016 Trip spans 8 days
Major Airline
Major Airline
PWM
ORD
2h 44m
nonstop
ORD
PWM
2h 25m
nonstop
Depart: Sun Oct 2 2016 Return: Sun Oct 9 2016 Trip spans 8 days
Delta
Delta
PWM
MDW
6h 19m
1 stop
MDW
PWM
4h 23m
1 stop
Select an airline:  United
Direct flights PWM to CHI on United
Flight # Depart PWM Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
4816 6:00 am 7:40 am Jun 9 - Jun 30
4816 6:01 am 7:50 am May 8 - Jun 5
3475 6:20 am 8:15 am Jun 4 - Jun 4
3608 6:20 am 8:15 am May 7 - May 28
4816 6:20 am 8:09 am May 6 - Jun 8
4109 9:06 am 11:00 am Jun 5 - Jun 5
4109 9:06 am 11:00 am May 8 - May 22
4109 9:20 am 11:14 am May 29 - May 29
4860 11:25 am 1:13 pm May 6 - Jun 8
4860 11:25 am 1:05 pm Jun 9 - Jun 24
4022 4:43 pm 6:35 pm May 22 - May 22
4022 4:43 pm 6:35 pm May 30 - May 30
4219 4:43 pm 6:35 pm Jun 6 - Jun 8
4219 4:43 pm 6:35 pm Jun 5 - Jun 5
4219 4:43 pm 6:35 pm May 26 - May 31
4219 4:43 pm 6:35 pm May 23 - May 25
4219 4:43 pm 6:35 pm May 5 - May 20
4219 4:43 pm 6:35 pm May 29 - Jun 3
4219 4:45 pm 6:35 pm Jun 9 - Jul 1
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We make every attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller
At KAYAK we don’t set prices, so it’s not possible for us to guarantee what other companies are selling.

We aggregate tons 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 don'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.

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

Portland
$282
Destination

Chicago
only $282
only $420