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

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youth
12-17
Child
2-11
Seat Infant
under 2
Lap Infant
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 21 2015 Return: Tue Sep 22 2015 Trip spans 2 days
American Airlines
American Airlines
PWM
3:40p
ORD
9:10p
5h 30m
1 stop
ORD
7:50a
PWM
3:02p
7h 12m
1 stop
Depart: Thu Oct 1 2015 Return: Mon Oct 5 2015 Trip spans 5 days
American Airlines
American Airlines
PWM
3:40p
ORD
9:10p
5h 30m
1 stop
ORD
9:45a
PWM
3:06p
5h 21m
1 stop
Depart: Sat Oct 31 2015 Return: Wed Nov 4 2015 Trip spans 5 days
American Airlines
American Airlines
PWM
10:30a
ORD
4:39p
6h 09m
1 stop
ORD
8:45a
PWM
2:06p
5h 21m
1 stop
Depart: Thu Sep 24 2015 Return: Mon Sep 28 2015 Trip spans 5 days
US Airways
US Airways
PWM
3:40p
ORD
9:10p
5h 30m
1 stop
ORD
2:49a
PWM
7:01a
4h 12m
1 stop
Depart: Wed Sep 30 2015 Return: Sun Oct 4 2015 Trip spans 5 days
US Airways
US Airways
PWM
3:40p
ORD
9:10p
5h 30m
1 stop
ORD
3:22p
PWM
7:18p
3h 56m
1 stop
Depart: Fri Oct 2 2015 Return: Sun Oct 4 2015 Trip spans 3 days
US Airways
US Airways
PWM
3:40p
ORD
9:10p
5h 30m
1 stop
ORD
3:22p
PWM
7:18p
3h 56m
1 stop
Depart: Sat Nov 14 2015 Return: Tue Nov 17 2015 Trip spans 4 days
American Airlines
American Airlines
PWM
3:05a
ORD
8:36a
5h 31m
1 stop
ORD
8:42a
PWM
2:04p
5h 22m
1 stop
Depart: Wed Oct 21 2015 Return: Wed Oct 28 2015 Trip spans 8 days
American Airlines
American Airlines
PWM
1:55p
ORD
6:54p
4h 59m
1 stop
ORD
9:45a
PWM
3:06p
5h 21m
1 stop
Depart: Fri Oct 23 2015 Return: Mon Oct 26 2015 Trip spans 4 days
American Airlines
American Airlines
PWM
1:55p
ORD
7:25p
5h 30m
1 stop
ORD
1:15p
PWM
6:33p
5h 18m
1 stop
Depart: Wed Sep 23 2015 Return: Wed Sep 30 2015 Trip spans 8 days
American Airlines
American Airlines
PWM
3:40p
ORD
9:10p
5h 30m
1 stop
ORD
2:45a
PWM
7:49a
5h 04m
1 stop
Depart: Fri Sep 18 2015 Return: Mon Sep 21 2015 Trip spans 4 days
American Airlines
American Airlines
PWM
3:40p
ORD
9:10p
5h 30m
1 stop
ORD
1:15p
PWM
6:33p
5h 18m
1 stop
Depart: Fri Sep 25 2015 Return: Sun Sep 27 2015 Trip spans 3 days
American Airlines
American Airlines
PWM
3:40p
ORD
9:10p
5h 30m
1 stop
ORD
2:00a
PWM
7:49a
5h 49m
1 stop
Depart: Thu Oct 29 2015 Return: Mon Nov 2 2015 Trip spans 5 days
American Airlines
American Airlines
PWM
3:10a
ORD
8:06a
4h 56m
1 stop
ORD
6:50a
PWM
2:06p
7h 16m
1 stop
Depart: Sat Sep 19 2015 Return: Mon Sep 21 2015 Trip spans 3 days
US Airways
US Airways
PWM
2:00a
ORD
8:29a
6h 29m
1 stop
ORD
2:49a
PWM
7:01a
4h 12m
1 stop
Depart: Sun Nov 1 2015 Return: Wed Nov 4 2015 Trip spans 4 days
American Airlines
American Airlines
PWM
3:45a
ORD
11:48a
8h 03m
1 stop
ORD
8:45a
PWM
2:06p
5h 21m
1 stop
Depart: Fri Oct 30 2015 Return: Sun Nov 1 2015 Trip spans 3 days
American Airlines
American Airlines
PWM
1:05p
ORD
6:07p
5h 02m
1 stop
ORD
1:00a
PWM
6:46a
5h 46m
1 stop
Depart: Tue Oct 13 2015 Return: Fri Oct 16 2015 Trip spans 4 days
JetBlue Airways
JetBlue Airways
PWM
2:00a
ORD
7:29a
5h 29m
1 stop
ORD
2:36p
PWM
6:54p
4h 18m
1 stop
Depart: Mon Nov 23 2015 Return: Fri Nov 27 2015 Trip spans 5 days
United
United
PWM
4:30a
ORD
9:25a
4h 55m
1 stop
ORD
3:36a
PWM
8:04a
4h 28m
1 stop
Depart: Tue Sep 22 2015 Return: Mon Sep 28 2015 Trip spans 7 days
Delta
Delta
PWM
2:50a
MDW
10:15a
7h 25m
1 stop
MDW
3:05a
PWM
12:06p
9h 01m
1 stop
Depart: Thu Dec 24 2015 Return: Thu Dec 31 2015 Trip spans 8 days
Delta
Delta
PWM
3:45a
ORD
8:40a
4h 55m
1 stop
ORD
4:00a
PWM
7:55a
3h 55m
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
3681 6:20 am 7:57 am Sep 14 - Sep 23
3681 6:20 am 7:57 am Sep 6 - Sep 13
3681 6:20 am 7:57 am Sep 15 - Sep 15
3681 6:22 am 7:59 am Sep 24 - Oct 14
3673 9:53 am 11:29 am Sep 28 - Sep 29
3673 9:53 am 11:35 am Oct 5 - Oct 23
3673 9:53 am 11:35 am Oct 3 - Oct 10
3673 9:53 am 11:35 am Sep 24 - Oct 4
3673 9:53 am 11:35 am Sep 26 - Sep 26
3666 9:56 am 11:29 am Sep 20 - Sep 20
3666 9:58 am 11:35 am Sep 12 - Sep 19
3666 9:58 am 11:35 am Sep 8 - Sep 11
3666 9:58 am 11:35 am Sep 14 - Sep 21
3666 9:58 am 11:35 am Sep 22 - Sep 22
3666 9:58 am 11:35 am Sep 16 - Sep 23
3666 9:58 am 11:35 am Sep 13 - Sep 13
3666 9:58 am 11:35 am Sep 15 - Sep 15
3634 1:10 pm 2:50 pm Sep 14 - Sep 21
3932 1:10 pm 2:55 pm Sep 9 - Sep 9
3634 1:15 pm 2:55 pm Sep 24 - Oct 16
3536 1:19 pm 3:04 pm Sep 12 - Sep 12
3634 1:19 pm 2:59 pm Sep 19 - Sep 23
3634 1:19 pm 2:59 pm Sep 10 - Sep 18
3634 1:19 pm 2:59 pm Sep 1 - Sep 8
5130 4:26 pm 6:15 pm Sep 4 - Sep 8
5130 4:26 pm 6:15 pm Sep 13 - Sep 20
5130 4:26 pm 6:15 pm Sep 17 - Sep 21
5130 4:26 pm 6:15 pm Sep 11 - Sep 11
5130 4:26 pm 6:15 pm Sep 23 - Sep 23
4219 4:31 pm 6:20 pm Sep 26 - Oct 24
4219 4:31 pm 6:20 pm Sep 24 - Oct 23
5130 4:33 pm 6:22 pm Sep 9 - Sep 10
5130 4:33 pm 6:22 pm Sep 16 - Sep 16
5130 4:34 pm 6:23 pm Sep 15 - Sep 15
5130 4:34 pm 6:23 pm Sep 22 - Sep 22
5130 4:41 pm 6:30 pm Sep 19 - Sep 19
5130 5:05 pm 6:54 pm Sep 12 - Sep 12
Airports
Origin

Portland
$204
Destination

Chicago
only $204
only $488