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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: Thu Jan 8 2015 Return: Sun Jan 11 2015 Trip spans 4 days
JetBlue Airways
JetBlue Airways
ORD
1:40p
PWM
5:58p
4h 18m
1 stop
PWM
1:05a
ORD
6:18a
5h 13m
1 stop
Depart: Sat Jan 10 2015 Return: Tue Jan 13 2015 Trip spans 4 days
US Airways
US Airways
ORD
2:30a
PWM
6:35a
4h 05m
1 stop
PWM
6:23a
ORD
10:55a
4h 32m
1 stop
Depart: Fri Jan 9 2015 Return: Sun Jan 11 2015 Trip spans 3 days
JetBlue Airways
JetBlue Airways
ORD
1:40p
PWM
5:58p
4h 18m
1 stop
PWM
1:05a
ORD
6:18a
5h 13m
1 stop
Depart: Sun Jan 11 2015 Return: Tue Jan 13 2015 Trip spans 3 days
US Airways
US Airways
ORD
1:00a
PWM
6:35a
5h 35m
1 stop
PWM
2:00a
ORD
7:13a
5h 13m
1 stop
Depart: Mon Jan 12 2015 Return: Tue Jan 13 2015 Trip spans 2 days
JetBlue Airways
JetBlue Airways
ORD
1:40p
PWM
5:58p
4h 18m
1 stop
PWM
10:16a
ORD
5:18p
7h 02m
1 stop
Depart: Fri Jan 16 2015 Return: Sun Jan 18 2015 Trip spans 3 days
JetBlue Airways
JetBlue Airways
ORD
1:40p
PWM
5:58p
4h 18m
1 stop
PWM
1:05a
ORD
6:18a
5h 13m
1 stop
Depart: Fri Jan 23 2015 Return: Sun Jan 25 2015 Trip spans 3 days
US Airways
US Airways
ORD
11:00a
PWM
4:01p
5h 01m
1 stop
PWM
3:45a
ORD
10:57a
7h 12m
1 stop
Depart: Tue Jan 27 2015 Return: Thu Jan 29 2015 Trip spans 3 days
US Airways
US Airways
ORD
8:55a
PWM
4:01p
7h 06m
1 stop
PWM
2:00a
ORD
7:13a
5h 13m
1 stop
Depart: Thu Feb 5 2015 Return: Sun Feb 15 2015 Trip spans 11 days
JetBlue Airways
JetBlue Airways
ORD
1:40p
PWM
5:58p
4h 18m
1 stop
PWM
1:05a
ORD
6:41a
5h 36m
1 stop
Depart: Fri Feb 6 2015 Return: Sun Feb 8 2015 Trip spans 3 days
US Airways
US Airways
ORD
8:55a
PWM
4:01p
7h 06m
1 stop
PWM
3:45a
ORD
10:57a
7h 12m
1 stop
Depart: Sun Feb 8 2015 Return: Thu Feb 19 2015 Trip spans 12 days
US Airways
US Airways
ORD
1:00a
PWM
6:39a
5h 39m
1 stop
PWM
6:23a
ORD
1:17p
6h 54m
1 stop
Depart: Mon Feb 9 2015 Return: Thu Feb 19 2015 Trip spans 11 days
US Airways
US Airways
ORD
7:05a
PWM
11:05a
4h 00m
1 stop
PWM
4:12a
ORD
8:58a
4h 46m
1 stop
Depart: Mon Mar 9 2015 Return: Mon Mar 23 2015 Trip spans 15 days
JetBlue Airways
JetBlue Airways
ORD
2:35p
PWM
6:59p
4h 24m
1 stop
PWM
2:00a
ORD
7:22a
5h 22m
1 stop
Depart: Wed Mar 11 2015 Return: Mon Mar 23 2015 Trip spans 13 days
JetBlue Airways
JetBlue Airways
ORD
2:35p
PWM
6:59p
4h 24m
1 stop
PWM
2:00a
ORD
7:22a
5h 22m
1 stop
Depart: Thu Jan 1 2015 Return: Thu Jan 15 2015 Trip spans 15 days
US Airways
US Airways
ORD
4:45a
PWM
11:06a
6h 21m
1 stop
PWM
2:00a
ORD
8:58a
6h 58m
1 stop
Depart: Mon Jan 5 2015 Return: Sun Jan 18 2015 Trip spans 14 days
American Airlines
American Airlines
ORD
6:40a
PWM
10:32a
3h 52m
1 stop
PWM
7:25a
ORD
12:23p
4h 58m
1 stop
Depart: Sat Mar 21 2015 Return: Tue Mar 24 2015 Trip spans 4 days
Multiple Airlines
Multiple Airlines
ORD
2:00a
PWM
10:39a
8h 39m
2 stops
PWM
11:33a
ORD
6:16p
6h 43m
1 stop
Depart: Mon May 4 2015 Return: Mon May 11 2015 Trip spans 8 days
United
United
ORD
10:30a
PWM
5:42p
7h 12m
2 stops
PWM
8:54a
ORD
5:59p
9h 05m
2 stops
Depart: Mon Jan 19 2015 Return: Tue Jan 20 2015 Trip spans 2 days
Delta
Delta
MDW
11:31a
PWM
5:42p
6h 11m
1 stop
PWM
11:20a
MDW
4:30p
5h 10m
1 stop
Depart: Sun Jan 4 2015 Return: Thu Jan 8 2015 Trip spans 5 days
Delta
Delta
ORD
1:50a
PWM
6:00a
4h 10m
1 stop
PWM
1:45a
ORD
9:16a
7h 31m
1 stop
Change your search
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
3679 7:55 am 11:06 am Dec 27 - Dec 27
5938 7:55 am 11:10 am Jan 3 - Jan 3
3625 7:59 am 11:10 am Dec 26 - Dec 28
3679 7:59 am 11:10 am Dec 18 - Dec 25
3692 7:59 am 11:10 am Jan 4 - Jan 4
3693 7:59 am 11:10 am Dec 29 - Jan 5
6069 1:15 pm 4:33 pm Jan 10 - Feb 7
3611 1:41 pm 4:52 pm Dec 26 - Dec 28
3633 1:41 pm 4:52 pm Jan 4 - Jan 4
3644 1:41 pm 4:52 pm Jan 1 - Jan 1
3692 1:41 pm 4:52 pm Dec 29 - Jan 5
3656 1:45 pm 4:59 pm Jan 6 - Feb 11
3692 1:45 pm 4:59 pm Jan 19 - Jan 25
3692 1:45 pm 4:59 pm Jan 11 - Jan 18
3693 1:45 pm 4:59 pm Jan 8 - Jan 16
3693 1:45 pm 4:59 pm Jan 22 - Feb 5
3693 1:45 pm 4:59 pm Jan 23 - Feb 9
3701 1:45 pm 4:56 pm Jan 3 - Jan 3
3611 1:50 pm 5:01 pm Dec 27 - Dec 27
3605 4:10 pm 7:21 pm Dec 31 - Dec 31
3605 6:51 pm 10:02 pm Dec 26 - Dec 26
3625 6:51 pm 10:02 pm Dec 27 - Dec 27
3663 6:51 pm 10:02 pm Dec 29 - Jan 2
3663 6:51 pm 10:02 pm Dec 30 - Dec 30
3605 7:01 pm 10:12 pm Jan 4 - Jan 4
3625 7:01 pm 10:12 pm Jan 3 - Jan 3
3664 7:01 pm 10:12 pm Dec 28 - Dec 28
3625 7:40 pm 10:51 pm Dec 25 - Dec 25
3663 8:00 pm 11:11 pm Jan 5 - Jan 5
Airports
Origin

Chicago
only $228
only $406
Destination

Portland
$228