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
Students
under 26
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: Sat Jan 14 2017 Return: Sat Jan 28 2017 Trip spans 15 days
American Airlines
American Airlines
PWM
ORD
5h 42m
1 stop
ORD
PWM
7h 03m
1 stop
Depart: Thu Jan 12 2017 Return: Tue Jan 17 2017 Trip spans 6 days
Delta
Delta
PWM
ORD
5h 10m
1 stop
ORD
PWM
4h 19m
1 stop
Depart: Thu Feb 23 2017 Return: Mon Feb 27 2017 Trip spans 5 days
Major Airline
Major Airline
PWM
ORD
6h 32m
1 stop
ORD
PWM
23h 44m
1 stop
Depart: Thu Feb 16 2017 Return: Sun Feb 19 2017 Trip spans 4 days
United
United
PWM
ORD
6h 36m
1 stop
ORD
PWM
4h 34m
1 stop
Depart: Sun Jun 11 2017 Return: Sun Jun 18 2017 Trip spans 8 days
JetBlue
JetBlue
PWM
ORD
6h 24m
1 stop
ORD
PWM
4h 16m
1 stop
Depart: Thu Jan 19 2017 Return: Sun Jan 22 2017 Trip spans 4 days
Southwest
Southwest
PWM
MDW
6h 35m
1 stop
MDW
PWM
6h 00m
1 stop
Depart: Tue Jan 10 2017 Return: Wed Jan 11 2017 Trip spans 2 days
American Airlines
American Airlines
PWM
ORD
4h 38m
1 stop
ORD
PWM
5h 38m
1 stop
Depart: Fri Jan 13 2017 Return: Tue Jan 17 2017 Trip spans 5 days
Delta
Delta
PWM
MDW
5h 23m
1 stop
MDW
PWM
5h 02m
1 stop
Depart: Wed Mar 1 2017 Return: Sun Mar 5 2017 Trip spans 5 days
Major Airline
Major Airline
PWM
ORD
5h 15m
1 stop
ORD
PWM
4h 39m
1 stop
Depart: Sat Jan 28 2017 Return: Tue Jan 31 2017 Trip spans 4 days
Delta
Delta
PWM
MDW
4h 54m
1 stop
MDW
PWM
5h 02m
1 stop
Depart: Fri May 5 2017 Return: Sun May 7 2017 Trip spans 3 days
Delta
Delta
PWM
ORD
4h 42m
1 stop
ORD
PWM
3h 53m
1 stop
Depart: Fri Apr 7 2017 Return: Mon Apr 10 2017 Trip spans 4 days
American Airlines
American Airlines
PWM
ORD
4h 27m
1 stop
ORD
PWM
4h 05m
1 stop
Depart: Sun Dec 25 2016 Return: Thu Dec 29 2016 Trip spans 5 days
Major Airline
Major Airline
PWM
ORD
5h 49m
nonstop
ORD
PWM
16h 55m
nonstop
Depart: Thu Jun 29 2017 Return: Tue Jul 4 2017 Trip spans 6 days
Delta
Delta
PWM
ORD
6h 46m
1 stop
ORD
PWM
4h 22m
1 stop
Depart: Thu Jan 19 2017 Return: Sun Jan 22 2017 Trip spans 4 days
Major Airline
Major Airline
PWM
ORD
19h 53m
1 stop
ORD
PWM
14h 53m
1 stop
Depart: Mon Dec 19 2016 Return: Sat Dec 31 2016 Trip spans 13 days
American Airlines
American Airlines
PWM
ORD
7h 41m
1 stop
ORD
PWM
5h 09m
1 stop
Depart: Sat Dec 17 2016 Return: Sat Dec 24 2016 Trip spans 8 days
Delta
Delta
PWM
MDW
6h 45m
1 stop
MDW
PWM
5h 47m
1 stop
Depart: Thu Mar 2 2017 Return: Sun Mar 5 2017 Trip spans 4 days
Delta
Delta
PWM
MDW
6h 43m
1 stop
MDW
PWM
5h 49m
1 stop
Depart: Mon Mar 6 2017 Return: Thu Mar 9 2017 Trip spans 4 days
Delta
Delta
PWM
ORD
5h 06m
1 stop
ORD
PWM
4h 06m
1 stop
Depart: Thu May 25 2017 Return: Mon May 29 2017 Trip spans 5 days
Delta
Delta
PWM
ORD
4h 42m
1 stop
ORD
PWM
4h 12m
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
3842 5:45 am 7:52 am Jan 4 - Jan 4
3812 6:05 am 8:12 am Jan 4 - Jan 4
4008 6:15 am 8:15 am Dec 18 - Dec 24
4008 6:15 am 8:15 am Dec 30 - Jan 3
4008 6:15 am 8:15 am Dec 26 - Jan 2
4008 6:15 am 8:15 am Dec 17 - Dec 23
4472 6:15 am 8:11 am Dec 29 - Dec 29
4645 6:15 am 8:15 am Dec 25 - Jan 1
4008 7:15 am 9:15 am Dec 31 - Dec 31
3809 1:03 pm 3:05 pm Dec 16 - Dec 24
3809 1:03 pm 3:05 pm Dec 26 - Jan 3
3809 1:03 pm 3:05 pm Dec 25 - Jan 1
4219 4:25 pm 6:29 pm Jan 7 - Jan 7
4219 4:25 pm 6:29 pm Jan 14 - Jan 14
4219 4:25 pm 6:29 pm Jan 4 - Feb 3
3892 4:28 pm 6:29 pm Dec 17 - Dec 17
4219 4:28 pm 6:29 pm Dec 28 - Jan 3
4219 4:28 pm 6:29 pm Dec 16 - Dec 26
4219 4:28 pm 6:29 pm Dec 18 - Dec 18
3892 5:11 pm 7:12 pm Dec 21 - Dec 21
3892 5:12 pm 7:13 pm Dec 30 - Dec 30
3892 5:19 pm 7:20 pm Dec 27 - Dec 27
* 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
$201
Destination

Chicago
only $201
only $204
Airlines Airline reviews

17 travelers who booked a flight from Portland to Chicago rated their chosen airlines with an average of 6.7.

Overall
6.8
Boarding
6.9
Crew
7.8
Comfort
6.0
Food
5.8
Entertainment
7.2