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.
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Book cheap flights from Chicago to Portland

(Round-trip)
Depart: Tue Aug 29 2017 Return: Wed Sep 6 2017 Trip spans 9 days
American Airlines
American Airlines
ORD
PWM
5h 06m
1 stop
PWM
ORD
7h 24m
1 stop
Depart: Sat Oct 21 2017 Return: Tue Oct 24 2017 Trip spans 4 days
Major Airline
Major Airline
ORD
PWM
5h 57m
nonstop
PWM
ORD
16h 40m
nonstop
Depart: Thu Dec 7 2017 Return: Mon Dec 11 2017 Trip spans 5 days
United
United
ORD
PWM
6h 05m
1 stop
PWM
ORD
5h 15m
1 stop
Depart: Sat Sep 9 2017 Return: Tue Sep 12 2017 Trip spans 4 days
Delta
Delta
MDW
PWM
6h 19m
1 stop
PWM
MDW
6h 17m
1 stop
Depart: Sat Sep 2 2017 Return: Wed Sep 6 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
PWM
5h 47m
1 stop
PWM
ORD
7h 24m
1 stop
Depart: Sat Sep 23 2017 Return: Tue Sep 26 2017 Trip spans 4 days
American Airlines
American Airlines
ORD
PWM
7h 37m
1 stop
PWM
ORD
5h 50m
1 stop
Depart: Tue Aug 15 2017 Return: Tue Aug 22 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
PWM
4h 14m
nonstop
PWM
ORD
6h 21m
nonstop
Depart: Tue Sep 12 2017 Return: Tue Sep 19 2017 Trip spans 8 days
Delta
Delta
MDW
PWM
8h 30m
1 stop
PWM
MDW
8h 37m
1 stop
Depart: Sat Sep 23 2017 Return: Tue Sep 26 2017 Trip spans 4 days
Delta
Delta
MDW
PWM
4h 19m
1 stop
PWM
MDW
8h 37m
1 stop
Depart: Thu Oct 19 2017 Return: Mon Oct 23 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
PWM
26h 40m
1 stop
PWM
ORD
26h 15m
1 stop
Depart: Thu Dec 7 2017 Return: Mon Dec 11 2017 Trip spans 5 days
Delta
Delta
MDW
PWM
8h 55m
1 stop
PWM
MDW
7h 22m
1 stop
Depart: Sat Sep 2 2017 Return: Sun Sep 3 2017 Trip spans 2 days
Major Airline
Major Airline
ORD
PWM
23h 06m
nonstop
PWM
ORD
5h 56m
nonstop
Depart: Sat Jul 15 2017 Return: Fri Jul 21 2017 Trip spans 7 days
Delta
Delta
MDW
PWM
4h 46m
1 stop
PWM
MDW
4h 31m
1 stop
Depart: Sat Jul 15 2017 Return: Sat Jul 22 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
PWM
5h 11m
nonstop
PWM
ORD
11h 30m
nonstop
Depart: Tue Aug 22 2017 Return: Tue Aug 29 2017 Trip spans 8 days
Delta
Delta
MDW
PWM
4h 52m
1 stop
PWM
MDW
6h 17m
1 stop
Depart: Thu Oct 12 2017 Return: Tue Oct 17 2017 Trip spans 6 days
Delta
Delta
MDW
PWM
3h 52m
1 stop
PWM
MDW
6h 17m
1 stop
Depart: Tue Aug 15 2017 Return: Tue Aug 22 2017 Trip spans 8 days
Delta
Delta
MDW
PWM
5h 33m
1 stop
PWM
MDW
7h 39m
2 stops
Depart: Thu Nov 23 2017 Return: Sun Nov 26 2017 Trip spans 4 days
Major Airline
Major Airline
ORD
PWM
15h 01m
nonstop
PWM
ORD
22h 35m
nonstop
Depart: Thu Jun 29 2017 Return: Sat Jul 8 2017 Trip spans 10 days
Delta
Delta
MDW
PWM
4h 04m
1 stop
PWM
MDW
4h 35m
1 stop
Depart: Sat Jul 1 2017 Return: Sun Jul 2 2017 Trip spans 2 days
Major Airline
Major Airline
ORD
PWM
8h 14m
nonstop
PWM
ORD
11h 30m
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 2 - Aug 27
4175 7:30 am 10:53 am Jul 2 - Jul 2
4551 7:30 am 10:49 am Jun 21 - Jul 1
4551 7:30 am 10:49 am Jul 3 - Jul 3
4551 7:30 am 10:49 am Jul 5 - Aug 13
5469 9:07 am 12:29 pm Jul 1 - Aug 15
4035 1:45 pm 5:15 pm Jun 21 - Jun 30
4035 1:50 pm 5:20 pm Jul 15 - Jul 30
4035 1:50 pm 5:20 pm Jul 1 - Jul 7
4035 1:50 pm 5:20 pm Jul 3 - Jul 9
4035 1:50 pm 5:20 pm Jul 10 - Jul 31
4035 1:50 pm 5:20 pm Jul 2 - Jul 4
5866 6:36 pm 10:05 pm Jul 22 - Aug 12
5866 6:39 pm 10:08 pm Jul 23 - Aug 13
5866 6:41 pm 10:10 pm Jul 8 - Jul 15
3561 6:45 pm 10:14 pm Jul 1 - Jul 1
3953 6:45 pm 10:14 pm Jul 3 - Jul 3
5866 6:45 pm 10:14 pm Jul 10 - Jul 21
5866 6:45 pm 10:14 pm Jul 2 - Jul 9
5866 6:45 pm 10:14 pm Jul 24 - Aug 3
4572 6:58 pm 10:22 pm Jun 21 - Jun 30
* 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.

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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.

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 $223
only $328
Destination

Portland
$223
Airlines Airline reviews

15 travelers who booked a flight from Chicago to Portland rated their chosen airlines with an average of 7.1.

Overall
7.3
Boarding
7.2
Crew
7.9
Comfort
6.7
Food
6.7
Entertainment
5.4