Find Cheap 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: Tue Aug 29 2017 Return: Wed Aug 30 2017 Trip spans 2 days
Major Airline
Major Airline
PWM
ORD
5h 56m
nonstop
ORD
PWM
20h 22m
nonstop
Depart: Wed Jun 28 2017 Return: Mon Jul 3 2017 Trip spans 6 days
American Airlines
American Airlines
PWM
ORD
7h 27m
1 stop
ORD
PWM
7h 12m
1 stop
Depart: Sun Sep 3 2017 Return: Tue Sep 5 2017 Trip spans 3 days
Delta
Delta
PWM
MDW
8h 07m
1 stop
MDW
PWM
8h 30m
1 stop
Depart: Fri Sep 15 2017 Return: Sun Sep 17 2017 Trip spans 3 days
United
United
PWM
ORD
16h 25m
1 stop
ORD
PWM
21h 20m
1 stop
Depart: Sat Sep 9 2017 Return: Tue Sep 12 2017 Trip spans 4 days
Major Airline
Major Airline
PWM
ORD
14h 03m
1 stop
ORD
PWM
5h 57m
1 stop
Depart: Mon Jul 3 2017 Return: Tue Jul 4 2017 Trip spans 2 days
American Airlines
American Airlines
PWM
ORD
5h 59m
1 stop
ORD
PWM
4h 57m
1 stop
Depart: Tue Oct 17 2017 Return: Mon Oct 23 2017 Trip spans 7 days
Delta
Delta
PWM
MDW
8h 37m
1 stop
MDW
PWM
8h 25m
1 stop
Depart: Mon Oct 16 2017 Return: Mon Oct 23 2017 Trip spans 8 days
Major Airline
Major Airline
PWM
ORD
6h 00m
nonstop
ORD
PWM
5h 57m
nonstop
Depart: Fri Dec 1 2017 Return: Sun Dec 3 2017 Trip spans 3 days
Delta
Delta
PWM
ORD
5h 52m
1 stop
ORD
PWM
4h 22m
1 stop
Depart: Thu Sep 21 2017 Return: Fri Sep 22 2017 Trip spans 2 days
Major Airline
Major Airline
PWM
ORD
14h 03m
nonstop
ORD
PWM
20h 27m
nonstop
Depart: Thu Jul 20 2017 Return: Sat Jul 22 2017 Trip spans 3 days
Delta
Delta
PWM
MDW
4h 03m
1 stop
MDW
PWM
4h 46m
1 stop
Depart: Fri Aug 4 2017 Return: Mon Aug 7 2017 Trip spans 4 days
Delta
Delta
PWM
MDW
4h 03m
1 stop
MDW
PWM
7h 09m
1 stop
Depart: Sat Oct 7 2017 Return: Mon Oct 9 2017 Trip spans 3 days
Major Airline
Major Airline
PWM
ORD
26h 15m
nonstop
ORD
PWM
5h 57m
nonstop
Depart: Sat Sep 2 2017 Return: Sat Sep 9 2017 Trip spans 8 days
Delta
Delta
PWM
MDW
4h 29m
1 stop
MDW
PWM
4h 19m
1 stop
Depart: Sat Aug 12 2017 Return: Tue Aug 15 2017 Trip spans 4 days
Major Airline
Major Airline
PWM
ORD
11h 30m
nonstop
ORD
PWM
10h 17m
nonstop
Depart: Thu Nov 2 2017 Return: Tue Nov 7 2017 Trip spans 6 days
Delta
Delta
PWM
ORD
5h 46m
1 stop
ORD
PWM
4h 04m
1 stop
Depart: Thu Nov 2 2017 Return: Tue Nov 7 2017 Trip spans 6 days
Delta
Delta
PWM
MDW
4h 14m
1 stop
MDW
PWM
4h 07m
1 stop
Depart: Fri Dec 1 2017 Return: Sun Dec 3 2017 Trip spans 3 days
Delta
Delta
PWM
MDW
4h 20m
1 stop
MDW
PWM
4h 12m
1 stop
Depart: Sat Dec 23 2017 Return: Sat Dec 30 2017 Trip spans 8 days
Delta
Delta
PWM
ORD
4h 22m
1 stop
ORD
PWM
6h 25m
1 stop
Depart: Fri Jul 28 2017 Return: Mon Jul 31 2017 Trip spans 4 days
Delta
Delta
PWM
MDW
4h 03m
1 stop
MDW
PWM
4h 47m
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
3779 6:25 am 8:15 am Jul 4 - Jul 4
5739 6:25 am 8:13 am Jul 11 - Aug 14
5739 6:25 am 8:13 am Jul 3 - Jul 10
5513 9:59 am 11:45 am Jul 2 - Aug 13
4568 11:25 am 1:08 pm Jul 10 - Aug 11
4568 11:25 am 1:08 pm Jul 1 - Jul 7
4572 11:25 am 1:08 pm Jul 8 - Aug 13
5553 1:05 pm 2:52 pm Jul 1 - Aug 14
4219 4:40 pm 6:38 pm Jul 1 - Aug 14
4219 5:00 pm 6:58 pm Jul 5 - Aug 11
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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Airports
Origin

Portland
$262
Destination

Chicago
only $262
only $328
Airlines Airline reviews

23 travelers who booked a flight from Portland to Chicago rated their chosen airlines with an average of 6.1.

Overall
6.0
Boarding
6.4
Crew
7.1
Comfort
5.5
Food
5.3
Entertainment
6.0