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: Thu Jun 2 2016 Return: Tue Jun 7 2016 Trip spans 6 days
JetBlue
JetBlue
PWM
ORD
6h 23m
1 stop
ORD
PWM
5h 13m
1 stop
Depart: Tue Jul 12 2016 Return: Tue Jul 19 2016 Trip spans 8 days
JetBlue
JetBlue
PWM
ORD
6h 13m
1 stop
ORD
PWM
5h 23m
1 stop
Depart: Thu Aug 25 2016 Return: Tue Aug 30 2016 Trip spans 6 days
JetBlue
JetBlue
PWM
ORD
6h 13m
1 stop
ORD
PWM
5h 23m
1 stop
Depart: Fri Jun 3 2016 Return: Mon Jun 6 2016 Trip spans 4 days
JetBlue
JetBlue
PWM
ORD
8h 24m
1 stop
ORD
PWM
5h 13m
1 stop
Depart: Wed Aug 17 2016 Return: Sun Aug 21 2016 Trip spans 5 days
JetBlue
JetBlue
PWM
ORD
6h 13m
1 stop
ORD
PWM
5h 04m
1 stop
Depart: Fri May 6 2016 Return: Sun May 8 2016 Trip spans 3 days
JetBlue
JetBlue
PWM
ORD
6h 23m
1 stop
ORD
PWM
4h 23m
1 stop
Depart: Sat Mar 5 2016 Return: Tue Mar 8 2016 Trip spans 4 days
American Airlines
American Airlines
PWM
ORD
20h 23m
1 stop
ORD
PWM
7h 59m
2 stops
Depart: Fri Feb 26 2016 Return: Mon Mar 7 2016 Trip spans 11 days
American Airlines
American Airlines
PWM
ORD
18h 02m
1 stop
ORD
PWM
8h 32m
2 stops
Depart: Thu Jul 28 2016 Return: Mon Aug 1 2016 Trip spans 5 days
JetBlue
JetBlue
PWM
ORD
6h 13m
1 stop
ORD
PWM
5h 04m
1 stop
Depart: Tue Apr 5 2016 Return: Wed Apr 13 2016 Trip spans 9 days
United
United
PWM
ORD
4h 59m
1 stop
ORD
PWM
5h 25m
1 stop
Depart: Thu Jun 16 2016 Return: Sun Jun 19 2016 Trip spans 4 days
JetBlue
JetBlue
PWM
ORD
6h 13m
1 stop
ORD
PWM
6h 00m
1 stop
Depart: Tue May 24 2016 Return: Sun May 29 2016 Trip spans 6 days
United
United
PWM
ORD
4h 36m
1 stop
ORD
PWM
4h 44m
1 stop
Depart: Sat May 14 2016 Return: Sat May 21 2016 Trip spans 8 days
United
United
PWM
ORD
4h 36m
1 stop
ORD
PWM
4h 29m
1 stop
Depart: Wed Mar 2 2016 Return: Sat Mar 5 2016 Trip spans 4 days
United
United
PWM
ORD
7h 22m
2 stops
ORD
PWM
21h 37m
1 stop
Depart: Mon Mar 28 2016 Return: Wed Mar 30 2016 Trip spans 3 days
JetBlue
JetBlue
PWM
ORD
5h 25m
1 stop
ORD
PWM
5h 12m
1 stop
Depart: Thu Apr 7 2016 Return: Sun Apr 10 2016 Trip spans 4 days
United
United
PWM
ORD
13h 41m
1 stop
ORD
PWM
11h 19m
1 stop
Depart: Thu Apr 14 2016 Return: Sun Apr 17 2016 Trip spans 4 days
JetBlue
JetBlue
PWM
ORD
5h 25m
1 stop
ORD
PWM
7h 32m
1 stop
Depart: Fri Mar 4 2016 Return: Wed Mar 9 2016 Trip spans 6 days
Delta
Delta
PWM
MDW
15h 28m
1 stop
MDW
PWM
15h 36m
1 stop
Depart: Wed Apr 20 2016 Return: Mon Apr 25 2016 Trip spans 6 days
Delta
Delta
PWM
MDW
6h 48m
1 stop
MDW
PWM
16h 46m
1 stop
Depart: Tue Mar 29 2016 Return: Sun Apr 3 2016 Trip spans 6 days
Delta
Delta
PWM
MDW
9h 26m
2 stops
MDW
PWM
16h 46m
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
3587 5:40 am 7:29 am Mar 5 - Mar 5
3587 5:40 am 7:29 am Mar 12 - Mar 12
3587 5:40 am 7:29 am Mar 19 - Mar 19
3587 6:20 am 8:09 am Mar 6 - Mar 6
3677 6:20 am 8:09 am Mar 13 - Mar 13
4008 6:20 am 8:09 am Mar 4 - Mar 11
4008 6:20 am 8:09 am Mar 14 - Mar 21
4816 6:20 am 8:03 am Mar 20 - Mar 25
4219 4:31 pm 6:29 pm Mar 1 - Mar 1
3604 4:37 pm 6:35 pm Feb 11 - Mar 2
4219 4:37 pm 6:35 pm Feb 13 - Feb 20
4219 4:37 pm 6:35 pm Feb 21 - Feb 28
4219 4:41 pm 6:29 pm Mar 18 - Mar 18
4219 4:47 pm 6:35 pm Mar 3 - Mar 11
4219 4:47 pm 6:35 pm Mar 14 - Mar 21
4219 5:02 pm 7:00 pm Feb 19 - Feb 26
4219 5:02 pm 6:50 pm Mar 12 - Mar 12
3637 5:12 pm 7:00 pm Mar 19 - Mar 19
4219 5:19 pm 7:07 pm Mar 5 - Mar 5
4219 5:25 pm 7:13 pm Mar 13 - Mar 20
4219 5:25 pm 7:13 pm Mar 6 - Mar 6
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We make every attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller
At KAYAK we don’t set prices, so it’s not possible for us to guarantee what other companies are selling.

We aggregate tons 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 don'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.

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
$276
Destination

Chicago
only $276
only $442