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

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 Chicago to Portland

(Round-trip)
Depart: Fri May 6 2016 Return: Mon May 9 2016 Trip spans 4 days
United
United
ORD
PWM
2h 22m
nonstop
PWM
ORD
2h 48m
nonstop
Depart: Fri Jun 3 2016 Return: Sat Jun 4 2016 Trip spans 2 days
JetBlue
JetBlue
ORD
PWM
5h 13m
1 stop
PWM
ORD
6h 23m
1 stop
Depart: Thu Sep 22 2016 Return: Mon Sep 26 2016 Trip spans 5 days
Southwest
Southwest
MDW
PWM
5h 20m
1 stop
PWM
MDW
5h 40m
1 stop
Depart: Mon May 23 2016 Return: Wed May 25 2016 Trip spans 3 days
Delta
Delta
MDW
PWM
7h 30m
2 stops
PWM
MDW
7h 47m
2 stops
Depart: Mon Jul 25 2016 Return: Mon Aug 1 2016 Trip spans 8 days
Major Airline
Major Airline
MDW
PWM
4h 25m
1 stop
PWM
MDW
6h 59m
1 stop
Depart: Sat May 7 2016 Return: Mon May 9 2016 Trip spans 3 days
United
United
ORD
PWM
2h 20m
nonstop
PWM
ORD
2h 48m
nonstop
Depart: Tue Aug 30 2016 Return: Sun Sep 4 2016 Trip spans 6 days
JetBlue
JetBlue
ORD
PWM
5h 23m
1 stop
PWM
ORD
6h 23m
1 stop
Depart: Sat Sep 3 2016 Return: Fri Sep 9 2016 Trip spans 7 days
JetBlue
JetBlue
ORD
PWM
5h 23m
1 stop
PWM
ORD
6h 15m
1 stop
Depart: Mon Oct 24 2016 Return: Mon Oct 31 2016 Trip spans 8 days
JetBlue
JetBlue
ORD
PWM
5h 28m
1 stop
PWM
ORD
5h 07m
1 stop
Depart: Thu Oct 27 2016 Return: Mon Oct 31 2016 Trip spans 5 days
JetBlue
JetBlue
ORD
PWM
5h 28m
1 stop
PWM
ORD
5h 07m
1 stop
Depart: Fri Oct 28 2016 Return: Sun Oct 30 2016 Trip spans 3 days
JetBlue
JetBlue
ORD
PWM
5h 28m
1 stop
PWM
ORD
5h 07m
1 stop
Depart: Thu May 26 2016 Return: Sun May 29 2016 Trip spans 4 days
Delta
Delta
MDW
PWM
9h 05m
2 stops
PWM
MDW
10h 57m
2 stops
Depart: Wed Nov 30 2016 Return: Tue Dec 6 2016 Trip spans 7 days
JetBlue
JetBlue
ORD
PWM
5h 04m
1 stop
PWM
ORD
5h 07m
1 stop
Depart: Sat Jun 11 2016 Return: Sat Jun 18 2016 Trip spans 8 days
Delta
Delta
MDW
PWM
4h 34m
1 stop
PWM
MDW
4h 53m
1 stop
Depart: Mon Jun 13 2016 Return: Mon Jun 20 2016 Trip spans 8 days
Delta
Delta
MDW
PWM
3h 53m
1 stop
PWM
MDW
9h 03m
1 stop
Depart: Tue Aug 2 2016 Return: Thu Aug 11 2016 Trip spans 10 days
JetBlue
JetBlue
ORD
PWM
5h 23m
1 stop
PWM
ORD
6h 12m
1 stop
Depart: Sat Jul 23 2016 Return: Sat Jul 30 2016 Trip spans 8 days
United
United
ORD
PWM
6h 47m
1 stop
PWM
ORD
7h 08m
1 stop
Depart: Mon Jun 20 2016 Return: Wed Jun 22 2016 Trip spans 3 days
Delta
Delta
MDW
PWM
3h 53m
1 stop
PWM
MDW
4h 31m
1 stop
Depart: Wed Sep 21 2016 Return: Mon Sep 26 2016 Trip spans 6 days
JetBlue
JetBlue
ORD
PWM
5h 28m
1 stop
PWM
ORD
6h 15m
1 stop
Depart: Wed Jul 13 2016 Return: Wed Jul 20 2016 Trip spans 8 days
Major Airline
Major Airline
ORD
PWM
2h 25m
nonstop
PWM
ORD
2h 40m
nonstop
Select an airline:  United
Direct flights CHI to PWM on United
Flight # Depart ORD Arrive PWM Sun Mon Tue Wed Thu Fri Sat Valid Between
4871 7:29 am 10:49 am May 6 - Jun 8
4871 7:30 am 10:50 am Jun 10 - Jun 24
4871 7:30 am 10:50 am May 7 - Jun 9
3758 11:05 am 2:27 pm May 28 - May 28
4035 1:45 pm 5:19 pm Jun 9 - Jun 24
4035 1:51 pm 5:13 pm Jun 6 - Jun 8
4035 1:51 pm 5:13 pm May 8 - May 22
4035 1:51 pm 5:13 pm May 24 - May 24
4035 1:51 pm 5:13 pm May 29 - May 29
4035 1:51 pm 5:13 pm May 5 - May 23
4035 1:51 pm 5:13 pm May 25 - Jun 3
4035 1:51 pm 5:13 pm Jun 5 - Jun 5
4035 1:51 pm 5:13 pm May 30 - May 30
4035 2:45 pm 6:07 pm Jun 4 - Jun 4
4035 2:45 pm 6:07 pm May 7 - May 21
4801 6:10 pm 9:34 pm Jun 9 - Jun 30
3765 7:15 pm 10:37 pm May 6 - Jun 3
4801 7:15 pm 10:33 pm May 5 - Jun 8
* 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

Chicago
only $278
only $410
Destination

Portland
$278