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: Sat Sep 10 2016 Return: Tue Sep 13 2016 Trip spans 4 days
Depart: Wed Oct 19 2016 Return: Wed Oct 26 2016 Trip spans 8 days
Depart: Tue Jan 31 2017 Return: Thu Feb 2 2017 Trip spans 3 days
Depart: Thu Aug 18 2016 Return: Tue Aug 30 2016 Trip spans 13 days
Depart: Sat Nov 5 2016 Return: Wed Nov 9 2016 Trip spans 5 days
Depart: Wed Aug 24 2016 Return: Mon Aug 29 2016 Trip spans 6 days
Depart: Thu Sep 15 2016 Return: Mon Sep 19 2016 Trip spans 5 days
Depart: Tue Aug 2 2016 Return: Tue Aug 9 2016 Trip spans 8 days
Depart: Fri Oct 14 2016 Return: Mon Oct 17 2016 Trip spans 4 days
Depart: Thu Aug 25 2016 Return: Tue Aug 30 2016 Trip spans 6 days
Depart: Wed Jan 4 2017 Return: Sun Jan 8 2017 Trip spans 5 days
Depart: Thu Sep 15 2016 Return: Sun Sep 18 2016 Trip spans 4 days
Depart: Fri Aug 26 2016 Return: Sun Aug 28 2016 Trip spans 3 days
Depart: Fri Oct 28 2016 Return: Mon Oct 31 2016 Trip spans 4 days
Depart: Fri Sep 2 2016 Return: Sun Sep 4 2016 Trip spans 3 days
Depart: Thu Oct 13 2016 Return: Sun Oct 16 2016 Trip spans 4 days
Depart: Sat Nov 5 2016 Return: Wed Nov 9 2016 Trip spans 5 days
Depart: Thu Nov 10 2016 Return: Sun Nov 13 2016 Trip spans 4 days
Depart: Sun Nov 20 2016 Return: Thu Nov 24 2016 Trip spans 5 days
Depart: Thu Nov 24 2016 Return: Tue Nov 29 2016 Trip spans 6 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
3479 5:45 am 7:31 am Aug 16 - Aug 16
1564 5:50 am 7:28 am Jul 31 - Aug 14
4008 5:50 am 7:34 am Aug 4 - Aug 15
4008 5:50 am 7:34 am Aug 1 - Aug 3
4008 5:50 am 7:34 am Aug 9 - Aug 10
4008 5:50 am 7:34 am Aug 6 - Aug 13
3470 6:00 am 7:46 am Aug 31 - Sep 3
3479 6:00 am 7:46 am Aug 17 - Aug 29
3479 6:00 am 7:46 am Aug 18 - Aug 30
3600 6:00 am 7:46 am Aug 27 - Aug 27
3636 6:00 am 7:46 am Aug 20 - Aug 20
4802 6:00 am 7:40 am Aug 21 - Aug 28
657 9:06 am 10:49 am Aug 21 - Aug 28
4505 11:00 am 12:49 pm Aug 31 - Sep 6
4618 11:00 am 12:49 pm Aug 17 - Aug 29
4618 11:00 am 12:49 pm Aug 20 - Aug 27
4662 11:00 am 12:49 pm Aug 16 - Aug 30
4700 11:00 am 12:49 pm Sep 3 - Sep 3
4565 11:15 am 1:04 pm Aug 21 - Aug 28
3809 11:25 am 1:10 pm Aug 4 - Aug 10
4860 11:25 am 1:05 pm Jul 26 - Aug 3
4860 11:25 am 1:05 pm Aug 5 - Aug 15
3408 1:10 pm 2:59 pm Sep 3 - Sep 3
3809 1:10 pm 2:59 pm Aug 20 - Aug 27
3809 1:10 pm 2:59 pm Aug 16 - Sep 2
3809 1:10 pm 2:59 pm Aug 21 - Aug 28
1987 1:16 pm 2:54 pm Jul 31 - Aug 14
3479 1:25 pm 3:09 pm Jul 26 - Aug 15
1987 1:26 pm 3:04 pm Jul 30 - Aug 6
1987 1:26 pm 3:04 pm Aug 13 - Aug 13
4219 4:40 pm 6:26 pm Aug 16 - Sep 6
4860 4:40 pm 6:20 pm Aug 21 - Aug 28
4219 4:43 pm 6:28 pm Aug 13 - Aug 13
4219 4:43 pm 6:33 pm Jul 30 - Aug 6
3324 4:45 pm 6:31 pm Aug 20 - Aug 27
4219 4:45 pm 6:35 pm Jul 26 - Aug 3
4219 4:45 pm 6:35 pm Aug 4 - Aug 14
4298 4:46 pm 6:36 pm Aug 15 - Aug 15
* 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,
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Airports
Origin

Portland
$224
Destination

Chicago
only $224
only $341