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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: Sat Sep 12 2015 Trip spans 4 days
JetBlue Airways
JetBlue Airways
ORD
2:25p
PWM
6:58p
4h 33m
1 stop
PWM
2:00a
ORD
7:25a
5h 25m
1 stop
Depart: Sat Sep 19 2015 Return: Sat Oct 3 2015 Trip spans 15 days
JetBlue Airways
JetBlue Airways
ORD
3:00a
PWM
9:27a
6h 27m
1 stop
PWM
11:15a
ORD
6:05p
6h 50m
1 stop
Depart: Tue Sep 22 2015 Return: Fri Sep 25 2015 Trip spans 4 days
JetBlue Airways
JetBlue Airways
ORD
2:25p
PWM
6:53p
4h 28m
1 stop
PWM
2:00a
ORD
7:20a
5h 20m
1 stop
Depart: Wed Sep 23 2015 Return: Fri Sep 25 2015 Trip spans 3 days
JetBlue Airways
JetBlue Airways
ORD
3:05a
PWM
7:52a
4h 47m
1 stop
PWM
2:00a
ORD
7:20a
5h 20m
1 stop
Depart: Wed Aug 26 2015 Return: Fri Aug 28 2015 Trip spans 3 days
American Airlines
American Airlines
ORD
8:20a
PWM
3:16p
6h 56m
1 stop
PWM
3:00a
ORD
8:05a
5h 05m
1 stop
Depart: Wed May 13 2015 Return: Sat May 23 2015 Trip spans 11 days
US Airways
US Airways
ORD
2:00a
PWM
5:54a
3h 54m
1 stop
PWM
8:25a
ORD
1:29p
5h 04m
1 stop
Depart: Sat May 9 2015 Return: Tue May 19 2015 Trip spans 11 days
JetBlue Airways
JetBlue Airways
ORD
2:00a
PWM
9:21a
7h 21m
1 stop
PWM
1:55a
ORD
7:19a
5h 24m
1 stop
Depart: Sun May 10 2015 Return: Tue May 19 2015 Trip spans 10 days
JetBlue Airways
JetBlue Airways
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
PWM
1:55a
ORD
7:19a
5h 24m
1 stop
Depart: Tue May 12 2015 Return: Sat May 16 2015 Trip spans 5 days
JetBlue Airways
JetBlue Airways
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
PWM
11:00a
ORD
6:35p
7h 35m
1 stop
Depart: Thu Sep 10 2015 Return: Sat Sep 26 2015 Trip spans 17 days
JetBlue Airways
JetBlue Airways
ORD
3:00a
PWM
7:58a
4h 58m
1 stop
PWM
2:00a
ORD
7:20a
5h 20m
1 stop
Depart: Mon Sep 21 2015 Return: Fri Sep 25 2015 Trip spans 5 days
JetBlue Airways
JetBlue Airways
ORD
3:00a
PWM
9:27a
6h 27m
1 stop
PWM
2:00a
ORD
7:20a
5h 20m
1 stop
Depart: Thu Sep 24 2015 Return: Fri Sep 25 2015 Trip spans 2 days
JetBlue Airways
JetBlue Airways
ORD
3:05a
PWM
7:52a
4h 47m
1 stop
PWM
2:00a
ORD
7:20a
5h 20m
1 stop
Depart: Sat Sep 26 2015 Return: Wed Sep 30 2015 Trip spans 5 days
JetBlue Airways
JetBlue Airways
ORD
3:05a
PWM
7:52a
4h 47m
1 stop
PWM
2:00a
ORD
7:20a
5h 20m
1 stop
Depart: Sun Sep 27 2015 Return: Wed Sep 30 2015 Trip spans 4 days
JetBlue Airways
JetBlue Airways
ORD
3:05a
PWM
7:52a
4h 47m
1 stop
PWM
2:00a
ORD
7:20a
5h 20m
1 stop
Depart: Mon Jun 1 2015 Return: Wed Jun 3 2015 Trip spans 3 days
US Airways
US Airways
ORD
3:10a
PWM
7:44a
4h 34m
1 stop
PWM
1:59p
ORD
6:55p
4h 56m
1 stop
Depart: Tue May 19 2015 Return: Wed May 27 2015 Trip spans 9 days
JetBlue Airways
JetBlue Airways
ORD
2:00a
PWM
9:21a
7h 21m
1 stop
PWM
1:55a
ORD
7:19a
5h 24m
1 stop
Depart: Wed May 27 2015 Return: Sat Jun 6 2015 Trip spans 11 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: Thu May 28 2015 Return: Sat Jun 6 2015 Trip spans 10 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: Thu Jun 11 2015 Return: Mon Jun 15 2015 Trip spans 5 days
Delta
Delta
MDW
9:50a
PWM
6:49p
8h 59m
1 stop
PWM
3:00a
MDW
3:53p
12h 53m
1 stop
Depart: Sat Jun 13 2015 Return: Fri Jun 19 2015 Trip spans 7 days
Delta
Delta
ORD
1:15p
PWM
6:47p
5h 32m
1 stop
PWM
8:25a
ORD
12:39p
4h 14m
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
3614 8:30 am 11:44 am May 16 - May 30
3712 8:40 am 11:54 am May 24 - May 24
3712 8:42 am 11:56 am May 10 - May 17
3712 8:44 am 11:58 am May 31 - May 31
3712 8:44 am 11:58 am May 6 - May 6
3712 8:55 am 12:09 pm May 9 - May 9
3712 9:00 am 12:14 pm Jun 3 - Jun 3
3712 9:00 am 12:14 pm May 7 - May 22
3712 9:00 am 12:14 pm May 26 - Jun 2
3712 9:00 am 12:14 pm May 25 - May 25
3712 9:15 am 12:27 pm May 3 - May 5
3712 9:15 am 12:27 pm May 4 - May 4
3508 1:55 pm 5:17 pm May 6 - Jun 3
6069 1:55 pm 5:17 pm May 24 - May 24
6069 1:55 pm 5:17 pm May 31 - May 31
6069 1:55 pm 5:17 pm May 10 - May 17
6069 2:00 pm 5:19 pm Apr 8 - May 5
3508 6:00 pm 9:20 pm May 9 - May 9
3511 6:00 pm 9:20 pm Jun 3 - Jun 3
3693 6:00 pm 9:16 pm May 24 - May 24
3693 6:00 pm 9:16 pm May 10 - May 17
3693 6:00 pm 9:16 pm May 16 - May 22
3693 6:00 pm 9:16 pm May 23 - May 25
3693 6:00 pm 9:16 pm May 26 - Jun 2
3693 6:00 pm 9:16 pm May 30 - May 30
3693 6:00 pm 9:16 pm May 31 - May 31
3693 6:00 pm 9:16 pm May 6 - May 15
3693 7:15 pm 10:30 pm Apr 20 - May 5
Airports
Origin

Chicago
only $228
only $512
Destination

Portland
$228