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Find Flight Deals from Chicago to Portland (CHI - PWM)

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

Book cheap flights from Chicago to Portland

(Round-trip)
Depart: Wed Sep 9 2015 Return: Thu Sep 10 2015 Trip spans 2 days
JetBlue Airways
JetBlue Airways
ORD
2:22p
PWM
6:58p
4h 36m
1 stop
PWM
1:50a
ORD
7:25a
5h 35m
1 stop
Depart: Thu Oct 22 2015 Return: Wed Oct 28 2015 Trip spans 7 days
JetBlue Airways
JetBlue Airways
ORD
3:00a
PWM
7:52a
4h 52m
1 stop
PWM
1:50a
ORD
7:13a
5h 23m
1 stop
Depart: Tue Nov 10 2015 Return: Sat Nov 14 2015 Trip spans 5 days
JetBlue Airways
JetBlue Airways
ORD
12:40p
PWM
5:52p
5h 12m
1 stop
PWM
7:11a
ORD
1:04p
5h 53m
1 stop
Depart: Sat Nov 14 2015 Return: Mon Nov 23 2015 Trip spans 10 days
JetBlue Airways
JetBlue Airways
ORD
12:40p
PWM
5:52p
5h 12m
1 stop
PWM
7:11a
ORD
1:04p
5h 53m
1 stop
Depart: Tue Sep 15 2015 Return: Tue Sep 22 2015 Trip spans 8 days
JetBlue Airways
JetBlue Airways
ORD
3:00a
PWM
7:58a
4h 58m
1 stop
PWM
9:35a
ORD
6:05p
8h 30m
1 stop
Depart: Thu Sep 24 2015 Return: Fri Sep 25 2015 Trip spans 2 days
JetBlue Airways
JetBlue Airways
ORD
3:00a
PWM
7:52a
4h 52m
1 stop
PWM
2:00a
ORD
7:25a
5h 25m
1 stop
Depart: Sat Oct 3 2015 Return: Mon Oct 5 2015 Trip spans 3 days
JetBlue Airways
JetBlue Airways
ORD
2:22p
PWM
6:53p
4h 31m
1 stop
PWM
11:15a
ORD
6:05p
6h 50m
1 stop
Depart: Sat Oct 17 2015 Return: Fri Oct 23 2015 Trip spans 7 days
JetBlue Airways
JetBlue Airways
ORD
3:00a
PWM
9:32a
6h 32m
1 stop
PWM
11:15a
ORD
6:05p
6h 50m
1 stop
Depart: Tue Oct 20 2015 Return: Sat Oct 24 2015 Trip spans 5 days
JetBlue Airways
JetBlue Airways
ORD
3:00a
PWM
7:52a
4h 52m
1 stop
PWM
11:15a
ORD
6:05p
6h 50m
1 stop
Depart: Thu Nov 12 2015 Return: Sun Nov 15 2015 Trip spans 4 days
JetBlue Airways
JetBlue Airways
ORD
12:40p
PWM
5:52p
5h 12m
1 stop
PWM
12:50a
ORD
6:13a
5h 23m
1 stop
Depart: Sat Sep 12 2015 Return: Sat Sep 19 2015 Trip spans 8 days
JetBlue Airways
JetBlue Airways
ORD
3:00a
PWM
9:27a
6h 27m
1 stop
PWM
9:35a
ORD
6:12p
8h 37m
1 stop
Depart: Mon Sep 21 2015 Return: Wed Sep 23 2015 Trip spans 3 days
JetBlue Airways
JetBlue Airways
ORD
2:22p
PWM
6:58p
4h 36m
1 stop
PWM
2:00a
ORD
7:25a
5h 25m
1 stop
Depart: Fri Nov 13 2015 Return: Thu Nov 19 2015 Trip spans 7 days
JetBlue Airways
JetBlue Airways
ORD
12:40p
PWM
5:52p
5h 12m
1 stop
PWM
10:00a
ORD
5:43p
7h 43m
1 stop
Depart: Tue Jun 9 2015 Return: Thu Jun 11 2015 Trip spans 3 days
JetBlue Airways
JetBlue Airways
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
PWM
1:55a
ORD
8:04a
6h 09m
1 stop
Depart: Wed Aug 12 2015 Return: Wed Aug 26 2015 Trip spans 15 days
JetBlue Airways
JetBlue Airways
ORD
2:00a
PWM
9:53a
7h 53m
1 stop
PWM
5:13a
ORD
11:36a
6h 23m
1 stop
Depart: Thu Aug 20 2015 Return: Mon Aug 24 2015 Trip spans 5 days
JetBlue Airways
JetBlue Airways
ORD
12:34p
PWM
7:06p
6h 32m
1 stop
PWM
11:34a
ORD
7:21p
7h 47m
1 stop
Depart: Wed Sep 23 2015 Return: Sun Sep 27 2015 Trip spans 5 days
American Airlines
American Airlines
ORD
10:00a
PWM
3:16p
5h 16m
1 stop
PWM
4:05a
ORD
11:25a
7h 20m
1 stop
Depart: Sun Aug 23 2015 Return: Sat Aug 29 2015 Trip spans 7 days
US Airways
US Airways
ORD
2:50a
PWM
8:15a
5h 25m
1 stop
PWM
3:10a
ORD
9:39a
6h 29m
1 stop
Depart: Tue Oct 6 2015 Return: Tue Oct 13 2015 Trip spans 8 days
Delta
Delta
MDW
12:45p
PWM
4:43p
3h 58m
1 stop
PWM
12:25p
MDW
5:15p
4h 50m
1 stop
Depart: Fri Oct 2 2015 Return: Wed Oct 7 2015 Trip spans 6 days
Delta
Delta
ORD
5:00a
PWM
10:46a
5h 46m
1 stop
PWM
12:25p
ORD
4:56p
4h 31m
1 stop
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
3637 6:00 am 9:18 am Jul 4 - Jul 4
3637 6:05 am 9:23 am Jul 2 - Jul 5
5905 7:55 am 11:19 am Jun 20 - Jun 20
5935 7:55 am 11:19 am Jun 27 - Jun 27
3449 8:46 am 12:10 pm Jun 6 - Jun 6
3583 8:46 am 12:10 pm Jun 13 - Jun 13
3712 8:46 am 12:06 pm Jul 1 - Jul 1
3712 8:46 am 12:06 pm Jun 8 - Jun 30
3712 8:46 am 12:06 pm Jun 7 - Jun 28
3712 8:46 am 12:06 pm Jun 4 - Jun 5
3712 8:59 am 12:19 pm Jul 2 - Jul 2
3712 8:59 am 12:19 pm Jul 3 - Jul 3
5938 8:59 am 12:23 pm Jul 4 - Jul 11
3712 9:00 am 12:14 pm Jun 3 - Jun 3
5938 11:10 am 2:34 pm Jun 20 - Jun 20
3257 11:11 am 2:35 pm Jun 27 - Jun 27
6069 1:47 pm 5:12 pm Jul 2 - Jul 9
6069 1:47 pm 5:12 pm Jul 4 - Jul 4
6069 1:47 pm 5:12 pm Jul 3 - Jul 3
3508 1:55 pm 5:17 pm May 21 - Jun 3
6069 2:00 pm 5:25 pm Jun 4 - Jun 30
6069 2:00 pm 5:25 pm Jun 6 - Jun 27
6069 2:00 pm 5:25 pm Jul 1 - Jul 1
3386 5:42 pm 9:05 pm Jul 3 - Jul 3
5975 5:42 pm 9:05 pm Jul 2 - Jul 9
4549 6:00 pm 9:20 pm Jun 3 - Jun 3
3637 6:02 pm 9:21 pm Jul 1 - Jul 1
3693 6:02 pm 9:21 pm Jun 27 - Jun 27
3693 6:02 pm 9:21 pm Jun 13 - Jun 13
5915 6:02 pm 9:25 pm Jun 9 - Jun 10
5915 6:02 pm 9:25 pm Jun 17 - Jun 24
5975 6:02 pm 9:25 pm Jun 11 - Jun 11
5975 6:02 pm 9:25 pm Jun 18 - Jun 25
5975 6:02 pm 9:25 pm Jun 5 - Jun 29
5975 6:02 pm 9:25 pm Jun 30 - Jun 30
5975 6:02 pm 9:25 pm Jun 4 - Jun 4
3650 6:11 pm 9:30 pm Jun 6 - Jun 6
3693 6:11 pm 9:30 pm Jun 20 - Jun 20
3699 6:11 pm 9:30 pm Jun 16 - Jun 16
5975 6:17 pm 9:40 pm Jun 23 - Jun 23
5905 8:50 pm 12:13 am Jun 7 - Jun 28
Airports
Origin

Chicago
only $228
only $524
Destination

Portland
$228