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 Mar 29 2017 Return: Tue Apr 4 2017 Trip spans 7 days
JetBlue
JetBlue
PWM
ORD
5h 16m
1 stop
ORD
PWM
12h 23m
1 stop
Depart: Sun Dec 18 2016 Return: Sat Jan 7 2017 Trip spans 21 days
Major Airline
Major Airline
PWM
ORD
27h 20m
nonstop
ORD
PWM
5h 07m
nonstop
Depart: Thu Oct 27 2016 Return: Mon Nov 7 2016 Trip spans 12 days
Delta
Delta
PWM
MDW
6h 27m
1 stop
MDW
PWM
4h 41m
1 stop
Depart: Sat Dec 24 2016 Return: Sat Dec 31 2016 Trip spans 8 days
American Airlines
American Airlines
PWM
ORD
5h 33m
1 stop
ORD
PWM
4h 47m
1 stop
Depart: Tue Jan 31 2017 Return: Thu Feb 2 2017 Trip spans 3 days
JetBlue
JetBlue
PWM
ORD
7h 52m
1 stop
ORD
PWM
5h 07m
1 stop
Depart: Tue Feb 14 2017 Return: Wed Feb 22 2017 Trip spans 9 days
Major Airline
Major Airline
PWM
ORD
19h 49m
1 stop
ORD
PWM
4h 55m
1 stop
Depart: Sat Nov 5 2016 Return: Mon Nov 7 2016 Trip spans 3 days
Delta
Delta
PWM
MDW
5h 14m
1 stop
MDW
PWM
3h 53m
1 stop
Depart: Wed Nov 2 2016 Return: Tue Nov 8 2016 Trip spans 7 days
JetBlue
JetBlue
PWM
ORD
12h 30m
1 stop
ORD
PWM
19h 18m
1 stop
Depart: Fri Oct 21 2016 Return: Tue Oct 25 2016 Trip spans 5 days
Major Airline
Major Airline
PWM
ORD
17h 35m
nonstop
ORD
PWM
14h 25m
nonstop
Depart: Wed Dec 21 2016 Return: Tue Jan 17 2017 Trip spans 28 days
Delta
Delta
PWM
MDW
4h 14m
1 stop
MDW
PWM
4h 17m
1 stop
Depart: Sun Feb 12 2017 Return: Wed Feb 22 2017 Trip spans 11 days
Delta
Delta
PWM
MDW
6h 40m
1 stop
MDW
PWM
4h 22m
1 stop
Depart: Wed Mar 29 2017 Return: Tue Apr 4 2017 Trip spans 7 days
Delta
Delta
PWM
MDW
4h 28m
1 stop
MDW
PWM
5h 37m
1 stop
Depart: Mon Nov 14 2016 Return: Fri Nov 18 2016 Trip spans 5 days
Delta
Delta
PWM
ORD
6h 39m
1 stop
ORD
PWM
10h 18m
2 stops
Depart: Mon Nov 14 2016 Return: Fri Nov 18 2016 Trip spans 5 days
Major Airline
Major Airline
PWM
MDW
6h 40m
1 stop
MDW
PWM
4h 45m
1 stop
Depart: Fri Mar 10 2017 Return: Sun Mar 12 2017 Trip spans 3 days
Major Airline
Major Airline
PWM
ORD
22h 57m
nonstop
ORD
PWM
15h 58m
nonstop
Depart: Fri Oct 28 2016 Return: Sun Oct 30 2016 Trip spans 3 days
Delta
Delta
PWM
MDW
4h 39m
1 stop
MDW
PWM
4h 58m
1 stop
Depart: Mon Mar 6 2017 Return: Fri Mar 10 2017 Trip spans 5 days
Delta
Delta
PWM
MDW
9h 43m
2 stops
MDW
PWM
3h 56m
1 stop
Depart: Sat Oct 29 2016 Return: Mon Oct 31 2016 Trip spans 3 days
Delta
Delta
PWM
ORD
6h 00m
1 stop
ORD
PWM
4h 22m
1 stop
Depart: Thu Oct 20 2016 Return: Sun Oct 23 2016 Trip spans 4 days
Delta
Delta
PWM
ORD
9h 33m
2 stops
ORD
PWM
6h 00m
1 stop
Depart: Sat Dec 24 2016 Return: Fri Dec 30 2016 Trip spans 7 days
Delta
Delta
PWM
MDW
4h 27m
1 stop
MDW
PWM
3h 52m
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
4008 5:40 am 7:26 am Oct 12 - Oct 12
4008 5:54 am 7:40 am Oct 26 - Oct 26
4008 6:00 am 7:46 am Oct 7 - Oct 18
4008 6:00 am 7:46 am Oct 19 - Oct 25
4008 6:00 am 7:46 am Oct 27 - Oct 29
4529 6:00 am 7:44 am Sep 26 - Oct 5
4596 6:00 am 7:40 am Oct 16 - Oct 23
4596 6:00 am 7:40 am Oct 6 - Oct 9
4618 6:15 am 8:15 am Oct 31 - Nov 5
4643 11:00 am 12:50 pm Sep 24 - Oct 5
1107 1:15 pm 2:58 pm Oct 6 - Oct 28
4716 1:15 pm 3:10 pm Oct 30 - Nov 4
4573 1:30 pm 3:10 pm Sep 26 - Oct 5
4219 4:34 pm 6:29 pm Oct 30 - Nov 4
3442 4:36 pm 6:25 pm Oct 22 - Oct 22
3494 4:36 pm 6:25 pm Oct 29 - Oct 29
3709 4:36 pm 6:25 pm Oct 8 - Oct 15
4219 4:40 pm 6:29 pm Oct 10 - Oct 27
4219 4:40 pm 6:29 pm Sep 24 - Oct 7
3709 4:46 pm 6:35 pm Oct 9 - Oct 23
4219 5:25 pm 7:14 pm Oct 28 - Oct 28
* 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

Portland
$202
Destination

Chicago
only $202
only $236