Find Deals on Flights from Chicago to Portland (CHI - PWM)

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.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago to Portland

(Round-trip)
Depart: Thu Sep 22 2016 Return: Tue Sep 27 2016 Trip spans 6 days
Depart: Tue Dec 13 2016 Return: Sat Dec 17 2016 Trip spans 5 days
Depart: Mon Aug 29 2016 Return: Tue Aug 30 2016 Trip spans 2 days
Depart: Mon Aug 29 2016 Return: Wed Sep 7 2016 Trip spans 10 days
Depart: Tue Oct 4 2016 Return: Tue Oct 11 2016 Trip spans 8 days
Depart: Sat Sep 17 2016 Return: Sat Sep 24 2016 Trip spans 8 days
Depart: Wed Oct 12 2016 Return: Thu Oct 20 2016 Trip spans 9 days
Depart: Sun Sep 11 2016 Return: Wed Sep 14 2016 Trip spans 4 days
Depart: Wed Nov 9 2016 Return: Tue Nov 15 2016 Trip spans 7 days
Depart: Tue Oct 18 2016 Return: Thu Oct 20 2016 Trip spans 3 days
Depart: Tue Aug 9 2016 Return: Sun Aug 14 2016 Trip spans 6 days
Depart: Thu Nov 3 2016 Return: Sun Nov 6 2016 Trip spans 4 days
Depart: Thu Nov 3 2016 Return: Sun Nov 6 2016 Trip spans 4 days
Depart: Sun Nov 20 2016 Return: Wed Nov 23 2016 Trip spans 4 days
Depart: Fri Sep 2 2016 Return: Mon Sep 5 2016 Trip spans 4 days
Depart: Tue Aug 23 2016 Return: Thu Aug 25 2016 Trip spans 3 days
Depart: Tue Dec 13 2016 Return: Sat Dec 17 2016 Trip spans 5 days
Depart: Tue Aug 23 2016 Return: Fri Aug 26 2016 Trip spans 4 days
Depart: Fri Sep 16 2016 Return: Wed Sep 21 2016 Trip spans 6 days
Depart: Sat Oct 1 2016 Return: Sat Oct 15 2016 Trip spans 15 days
Select an airline:  United
Direct flights CHI to PWM on United
Flight # Depart ORD Arrive PWM Sun Mon Tue Wed Thu Fri Sat Valid Between
4521 6:05 am 9:30 am Aug 16 - Aug 30
4562 6:05 am 9:30 am Aug 31 - Sep 6
3758 7:30 am 10:54 am Aug 9 - Aug 10
4871 7:30 am 10:50 am Aug 5 - Aug 15
283 9:05 am 12:25 pm Aug 13 - Aug 13
283 9:05 am 12:25 pm Aug 14 - Aug 14
283 9:05 am 12:25 pm Jul 30 - Aug 7
3491 9:10 am 12:35 pm Sep 3 - Sep 3
3758 9:10 am 12:35 pm Aug 26 - Aug 29
3758 9:10 am 12:35 pm Aug 20 - Aug 27
3758 9:10 am 12:35 pm Aug 19 - Aug 19
3758 9:10 am 12:35 pm Aug 18 - Aug 25
3758 9:10 am 12:35 pm Aug 16 - Aug 30
3758 9:10 am 12:35 pm Aug 31 - Sep 6
4609 9:10 am 12:35 pm Sep 4 - Sep 5
3478 9:25 am 12:50 pm Jul 28 - Aug 15
4836 10:40 am 2:00 pm Aug 21 - Aug 28
4035 1:45 pm 5:19 pm Jul 28 - Aug 11
4035 1:45 pm 5:10 pm Aug 16 - Sep 6
4035 1:45 pm 5:19 pm Jul 29 - Aug 15
4035 1:45 pm 5:10 pm Aug 21 - Aug 28
4035 1:45 pm 5:10 pm Sep 4 - Sep 4
681 1:45 pm 5:05 pm Aug 20 - Aug 27
520 2:35 pm 6:03 pm Jul 30 - Aug 13
3474 6:10 pm 9:39 pm Jul 28 - Aug 15
3373 6:15 pm 9:39 pm Aug 16 - Aug 16
3373 6:15 pm 9:39 pm Aug 23 - Aug 30
3422 6:15 pm 9:39 pm Aug 17 - Aug 24
3422 6:15 pm 9:39 pm Aug 18 - Aug 25
3439 6:15 pm 9:39 pm Aug 20 - Aug 27
3474 6:15 pm 9:39 pm Aug 21 - Aug 28
3508 6:15 pm 9:39 pm Aug 31 - Sep 2
3536 6:15 pm 9:39 pm Aug 22 - Aug 29
3575 6:15 pm 9:39 pm Sep 4 - Sep 4
3621 6:15 pm 9:39 pm Aug 19 - Aug 26
4787 6:15 pm 9:35 pm Sep 3 - Sep 3
3508 6:33 pm 9:57 pm Sep 6 - Sep 6
3765 6:35 pm 9:59 pm Sep 5 - Sep 5
4485 6:51 pm 10:20 pm Aug 7 - Aug 14
4790 8:50 pm 12:10 am Sep 3 - Sep 3
4795 8:50 pm 12:10 am Aug 20 - Aug 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

Chicago
only $242
only $404
Destination

Portland
$242