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: Mon Sep 19 2016 Return: Sat Sep 24 2016 Trip spans 6 days
Depart: Sat Feb 18 2017 Return: Sat Feb 25 2017 Trip spans 8 days
Depart: Sat Oct 22 2016 Return: Mon Oct 24 2016 Trip spans 3 days
Depart: Fri Sep 9 2016 Return: Sun Sep 11 2016 Trip spans 3 days
Depart: Fri Aug 26 2016 Return: Mon Aug 29 2016 Trip spans 4 days
Depart: Fri Dec 30 2016 Return: Mon Jan 16 2017 Trip spans 18 days
Depart: Wed Jan 11 2017 Return: Mon Jan 16 2017 Trip spans 6 days
Depart: Thu Dec 8 2016 Return: Sun Dec 11 2016 Trip spans 4 days
Depart: Mon Sep 12 2016 Return: Thu Sep 15 2016 Trip spans 4 days
Depart: Fri Sep 9 2016 Return: Sun Sep 11 2016 Trip spans 3 days
Depart: Sun Sep 18 2016 Return: Mon Sep 26 2016 Trip spans 9 days
Depart: Fri Sep 30 2016 Return: Sun Oct 2 2016 Trip spans 3 days
Depart: Tue Sep 6 2016 Return: Sun Sep 11 2016 Trip spans 6 days
Depart: Sat Oct 8 2016 Return: Mon Oct 10 2016 Trip spans 3 days
Depart: Sat Oct 29 2016 Return: Tue Nov 1 2016 Trip spans 4 days
Depart: Tue Nov 1 2016 Return: Sun Nov 6 2016 Trip spans 6 days
Depart: Sat Dec 10 2016 Return: Mon Dec 12 2016 Trip spans 3 days
Depart: Wed Oct 12 2016 Return: Sun Oct 16 2016 Trip spans 5 days
Depart: Thu Oct 6 2016 Return: Thu Oct 20 2016 Trip spans 15 days
Depart: Fri Oct 14 2016 Return: Sun Dec 4 2016 Trip spans 52 days
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
3470 6:00 am 7:46 am Aug 31 - Sep 3
3470 6:00 am 7:46 am Sep 6 - Sep 6
3479 6:00 am 7:46 am Aug 23 - Aug 30
3554 6:00 am 7:50 am Sep 7 - Sep 7
4008 6:00 am 7:46 am Sep 5 - Sep 5
4529 6:00 am 7:44 am Sep 16 - Oct 5
4529 6:00 am 7:44 am Sep 8 - Sep 15
4828 6:00 am 7:40 am Sep 4 - Sep 4
4008 6:20 am 8:10 am Sep 9 - Sep 9
4529 6:20 am 8:04 am Sep 10 - Sep 17
657 6:20 am 8:04 am Sep 18 - Oct 2
657 6:20 am 8:04 am Sep 11 - Sep 11
4529 7:06 am 8:50 am Sep 24 - Sep 24
4505 11:00 am 12:49 pm Aug 31 - Sep 6
4565 11:00 am 12:49 pm Sep 5 - Sep 5
4643 11:00 am 12:50 pm Sep 7 - Oct 5
4662 11:00 am 12:49 pm Aug 23 - Aug 30
4700 11:00 am 12:49 pm Sep 3 - Sep 3
4505 11:15 am 1:04 pm Sep 4 - Sep 4
3408 1:10 pm 2:59 pm Sep 3 - Sep 3
3809 1:10 pm 2:59 pm Aug 22 - Sep 2
3809 1:10 pm 2:59 pm Sep 6 - Sep 6
4500 1:10 pm 2:59 pm Sep 5 - Sep 5
1107 1:19 pm 2:59 pm Sep 11 - Oct 2
3809 1:25 pm 3:10 pm Sep 10 - Oct 1
3809 1:25 pm 3:10 pm Sep 8 - Sep 8
4532 1:25 pm 3:05 pm Sep 9 - Sep 9
4573 1:30 pm 3:10 pm Sep 15 - Oct 5
4573 1:30 pm 3:10 pm Sep 7 - Sep 14
3554 4:40 pm 6:29 pm Sep 11 - Oct 2
4219 4:40 pm 6:29 pm Sep 7 - Sep 19
4219 4:40 pm 6:26 pm Aug 22 - Sep 6
4219 4:40 pm 6:29 pm Sep 20 - Oct 7
4830 4:40 pm 6:20 pm Sep 4 - Sep 4
4219 4:41 pm 6:30 pm Sep 13 - Sep 13
* 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
$230
Destination

Chicago
only $230
only $332