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

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

Book cheap flights from Portland to Chicago

(Round-trip)
Depart: Wed Sep 23 2015 Return: Wed Sep 30 2015 Trip spans 8 days
American Airlines
American Airlines
PWM
10:35a
ORD
4:29p
5h 54m
1 stop
ORD
7:50a
PWM
3:02p
7h 12m
1 stop
Depart: Thu Sep 17 2015 Return: Sat Sep 19 2015 Trip spans 3 days
American Airlines
American Airlines
PWM
2:00a
ORD
8:29a
6h 29m
1 stop
ORD
9:45a
PWM
3:02p
5h 17m
1 stop
Depart: Fri Sep 25 2015 Return: Mon Sep 28 2015 Trip spans 4 days
American Airlines
American Airlines
PWM
1:05p
ORD
6:07p
5h 02m
1 stop
ORD
7:50a
PWM
3:02p
7h 12m
1 stop
Depart: Sat Sep 12 2015 Return: Sun Sep 20 2015 Trip spans 9 days
US Airways
US Airways
PWM
2:05p
ORD
6:54p
4h 49m
1 stop
ORD
3:22p
PWM
7:18p
3h 56m
1 stop
Depart: Fri Sep 11 2015 Return: Sun Sep 13 2015 Trip spans 3 days
American Airlines
American Airlines
PWM
4:00a
ORD
9:33a
5h 33m
1 stop
ORD
2:00a
PWM
7:49a
5h 49m
1 stop
Depart: Tue Oct 20 2015 Return: Sun Oct 25 2015 Trip spans 6 days
American Airlines
American Airlines
PWM
2:00a
ORD
8:29a
6h 29m
1 stop
ORD
3:15a
PWM
8:58a
5h 43m
1 stop
Depart: Mon Oct 26 2015 Return: Fri Oct 30 2015 Trip spans 5 days
American Airlines
American Airlines
PWM
2:00a
ORD
8:29a
6h 29m
1 stop
ORD
1:40a
PWM
8:58a
7h 18m
1 stop
Depart: Fri Sep 4 2015 Return: Tue Sep 8 2015 Trip spans 5 days
American Airlines
American Airlines
PWM
1:11p
ORD
6:06p
4h 55m
1 stop
ORD
4:30a
PWM
11:40a
7h 10m
1 stop
Depart: Fri Oct 30 2015 Return: Sun Nov 1 2015 Trip spans 3 days
American Airlines
American Airlines
PWM
2:00a
ORD
8:29a
6h 29m
1 stop
ORD
2:15a
PWM
7:58a
5h 43m
1 stop
Depart: Sun Nov 1 2015 Return: Thu Nov 5 2015 Trip spans 5 days
American Airlines
American Airlines
PWM
1:00a
ORD
7:29a
6h 29m
1 stop
ORD
9:00a
PWM
2:16p
5h 16m
1 stop
Depart: Sat Aug 29 2015 Return: Sun Aug 30 2015 Trip spans 2 days
American Airlines
American Airlines
PWM
2:05p
ORD
6:56p
4h 51m
1 stop
ORD
2:00a
PWM
5:53a
3h 53m
1 stop
Depart: Tue Jul 7 2015 Return: Tue Jul 14 2015 Trip spans 8 days
American Airlines
American Airlines
PWM
4:05a
ORD
11:06a
7h 01m
1 stop
ORD
9:55a
PWM
3:06p
5h 11m
1 stop
Depart: Wed Jul 8 2015 Return: Tue Jul 14 2015 Trip spans 7 days
American Airlines
American Airlines
PWM
8:07a
ORD
1:22p
5h 15m
1 stop
ORD
9:55a
PWM
3:06p
5h 11m
1 stop
Depart: Sat Jul 4 2015 Return: Tue Jul 7 2015 Trip spans 4 days
US Airways
US Airways
PWM
7:25a
ORD
12:02p
4h 37m
1 stop
ORD
2:00a
PWM
5:54a
3h 54m
1 stop
Depart: Tue Jul 14 2015 Return: Tue Jul 28 2015 Trip spans 15 days
American Airlines
American Airlines
PWM
8:07a
ORD
3:06p
6h 59m
1 stop
ORD
11:00a
PWM
6:35p
7h 35m
1 stop
Depart: Wed Jul 22 2015 Return: Tue Jul 28 2015 Trip spans 7 days
American Airlines
American Airlines
PWM
7:05a
ORD
1:22p
6h 17m
1 stop
ORD
1:00p
PWM
6:35p
5h 35m
1 stop
Depart: Wed Aug 5 2015 Return: Sat Aug 15 2015 Trip spans 11 days
American Airlines
American Airlines
PWM
1:50a
ORD
8:21a
6h 31m
1 stop
ORD
5:05a
PWM
12:37p
7h 32m
1 stop
Depart: Mon Sep 28 2015 Return: Thu Oct 1 2015 Trip spans 4 days
United
United
PWM
2:00a
ORD
10:31a
8h 31m
2 stops
ORD
12:30p
PWM
6:38p
6h 08m
2 stops
Depart: Wed Oct 14 2015 Return: Tue Oct 20 2015 Trip spans 7 days
Delta
Delta
PWM
12:50p
MDW
5:00p
4h 10m
1 stop
MDW
3:00a
PWM
6:55a
3h 55m
1 stop
Depart: Wed Aug 19 2015 Return: Tue Aug 25 2015 Trip spans 7 days
Delta
Delta
PWM
2:55a
ORD
7:41a
4h 46m
1 stop
ORD
6:45a
PWM
10:59a
4h 14m
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
3465 6:38 am 8:20 am Jul 6 - Aug 17
3465 6:38 am 8:20 am Jul 7 - Jul 28
3465 6:38 am 8:20 am Jul 8 - Jul 29
3631 6:38 am 8:14 am Aug 5 - Aug 5
3681 6:38 am 8:14 am Jul 12 - Aug 16
3922 6:38 am 8:20 am Aug 4 - Aug 11
3922 6:42 am 8:24 am Aug 1 - Aug 1
3922 6:42 am 8:24 am Aug 8 - Aug 8
3922 6:42 am 8:24 am Jul 11 - Jul 25
4269 9:16 am 10:58 am Jul 25 - Jul 25
4269 9:30 am 11:12 am Jul 11 - Jul 18
4269 9:30 am 11:12 am Aug 1 - Aug 8
3666 10:03 am 11:40 am Aug 7 - Aug 16
3666 10:03 am 11:40 am Aug 6 - Aug 10
3666 10:03 am 11:40 am Jul 6 - Aug 3
3634 1:08 pm 2:45 pm Jul 18 - Jul 25
3634 1:08 pm 2:45 pm Aug 8 - Aug 8
3932 1:08 pm 2:50 pm Jul 4 - Jul 11
3932 1:08 pm 2:50 pm Aug 1 - Aug 1
3479 1:17 pm 2:59 pm Jul 14 - Aug 4
3634 1:22 pm 2:59 pm Jul 12 - Jul 26
3634 1:22 pm 2:59 pm Aug 10 - Aug 17
3634 1:22 pm 2:59 pm Aug 9 - Aug 9
3634 1:22 pm 2:59 pm Jul 10 - Aug 6
3932 1:22 pm 3:04 pm Aug 2 - Aug 2
5982 1:22 pm 3:04 pm Aug 7 - Aug 7
4219 4:40 pm 6:20 pm Aug 9 - Aug 14
4219 4:40 pm 6:20 pm Jul 10 - Jul 24
4219 4:40 pm 6:20 pm Jul 21 - Aug 11
4219 4:40 pm 6:20 pm Jul 27 - Aug 7
4219 4:40 pm 6:20 pm Jul 14 - Jul 14
3514 4:41 pm 6:21 pm Jul 26 - Jul 26
3514 4:45 pm 6:25 pm Jul 18 - Jul 18
3514 4:45 pm 6:25 pm Jul 25 - Aug 1
4219 4:45 pm 6:25 pm Jul 11 - Jul 11
4219 4:45 pm 6:25 pm Aug 8 - Aug 15
5130 4:45 pm 6:25 pm Aug 2 - Aug 2
Airports
Origin

Portland
$279
Destination

Chicago
only $279
only $422