Find Cheap 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.
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 Chicago to Portland

(Round-trip)
Depart: Sat Sep 9 2017 Return: Wed Sep 13 2017 Trip spans 5 days
United
United
ORD
PWM
8h 32m
2 stops
PWM
ORD
5h 30m
1 stop
Depart: Fri Dec 29 2017 Return: Sun Dec 31 2017 Trip spans 3 days
American Airlines
American Airlines
ORD
PWM
6h 39m
1 stop
PWM
ORD
7h 56m
1 stop
Depart: Fri Jan 5 2018 Return: Mon Jan 15 2018 Trip spans 11 days
Delta
Delta
MDW
PWM
10h 19m
2 stops
PWM
MDW
8h 13m
2 stops
Depart: Tue Sep 12 2017 Return: Thu Sep 21 2017 Trip spans 10 days
United
United
ORD
PWM
7h 45m
2 stops
PWM
ORD
5h 26m
1 stop
Depart: Sat Aug 19 2017 Return: Thu Aug 24 2017 Trip spans 6 days
United
United
ORD
PWM
17h 10m
1 stop
PWM
ORD
5h 11m
1 stop
Depart: Fri Oct 13 2017 Return: Mon Oct 16 2017 Trip spans 4 days
American Airlines
American Airlines
ORD
PWM
5h 47m
1 stop
PWM
ORD
5h 58m
1 stop
Depart: Tue Aug 29 2017 Return: Thu Aug 31 2017 Trip spans 3 days
Delta
Delta
MDW
PWM
9h 17m
2 stops
PWM
MDW
8h 11m
2 stops
Depart: Sun Nov 19 2017 Return: Fri Nov 24 2017 Trip spans 6 days
American Airlines
American Airlines
ORD
PWM
7h 25m
1 stop
PWM
ORD
7h 00m
1 stop
Depart: Wed Sep 6 2017 Return: Tue Sep 12 2017 Trip spans 7 days
Delta
Delta
MDW
PWM
8h 28m
2 stops
PWM
MDW
8h 11m
2 stops
Depart: Wed Sep 20 2017 Return: Sun Sep 24 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
PWM
6h 51m
1 stop
PWM
ORD
5h 50m
1 stop
Depart: Sun Dec 17 2017 Return: Sat Dec 23 2017 Trip spans 7 days
United
United
ORD
PWM
15h 04m
2 stops
PWM
ORD
26h 30m
1 stop
Depart: Sat Sep 2 2017 Return: Wed Sep 6 2017 Trip spans 5 days
Delta
Delta
MDW
PWM
4h 02m
1 stop
PWM
MDW
9h 56m
2 stops
Depart: Sat Oct 21 2017 Return: Wed Oct 25 2017 Trip spans 5 days
Delta
Delta
MDW
PWM
6h 39m
2 stops
PWM
MDW
4h 14m
1 stop
Depart: Mon Nov 20 2017 Return: Wed Nov 29 2017 Trip spans 10 days
Delta
Delta
MDW
PWM
10h 19m
2 stops
PWM
MDW
6h 47m
2 stops
Depart: Mon Jul 31 2017 Return: Fri Aug 4 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
PWM
4h 56m
1 stop
PWM
ORD
6h 37m
1 stop
Depart: Fri Dec 29 2017 Return: Sun Dec 31 2017 Trip spans 3 days
Delta
Delta
MDW
PWM
13h 50m
1 stop
PWM
MDW
4h 19m
1 stop
Depart: Thu Jul 27 2017 Return: Wed Aug 2 2017 Trip spans 7 days
American Airlines
American Airlines
ORD
PWM
7h 11m
1 stop
PWM
ORD
7h 15m
1 stop
Depart: Thu Aug 17 2017 Return: Wed Aug 23 2017 Trip spans 7 days
United
United
ORD
PWM
2h 17m
nonstop
PWM
ORD
2h 46m
nonstop
Depart: Fri Aug 25 2017 Return: Sun Aug 27 2017 Trip spans 3 days
Delta
Delta
MDW
PWM
6h 50m
1 stop
PWM
MDW
10h 00m
2 stops
Depart: Thu Aug 31 2017 Return: Mon Sep 4 2017 Trip spans 5 days
United
United
ORD
PWM
2h 28m
nonstop
PWM
ORD
2h 46m
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
5475 6:00 am 9:23 am Jul 23 - Aug 27
4551 7:30 am 10:49 am Jul 22 - Aug 13
4551 7:30 am 10:49 am Aug 15 - Sep 1
5639 7:30 am 10:49 am Aug 14 - Aug 14
5469 9:07 am 12:29 pm Aug 19 - Sep 2
5469 9:07 am 12:29 pm Jul 22 - Aug 15
5469 9:20 am 12:37 pm Aug 16 - Sep 5
4035 1:45 pm 5:15 pm Aug 1 - Aug 18
4035 1:45 pm 5:15 pm Aug 19 - Sep 5
4035 1:45 pm 5:15 pm Aug 5 - Aug 13
5866 6:36 pm 10:05 pm Jul 22 - Aug 12
5866 6:38 pm 10:06 pm Aug 16 - Sep 4
5866 6:39 pm 10:08 pm Jul 23 - Aug 13
5866 6:40 pm 10:08 pm Aug 15 - Aug 15
5866 6:40 pm 10:09 pm Aug 4 - Aug 14
5866 6:41 pm 10:09 pm Aug 19 - Sep 3
5866 6:45 pm 10:14 pm Jul 24 - Aug 3
* 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

Chicago
only $300
only $358
Destination

Portland
$300
Airlines Airline reviews

16 travelers who booked a flight from Chicago to Portland rated their chosen airlines with an average of 7.0.

Overall
8.0
Boarding
7.9
Crew
8.5
Comfort
7.2
Food
7.0
Entertainment
5.9