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Find Deals on Flights 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: Tue Aug 18 2015 Return: Tue Aug 25 2015 Trip spans 8 days
American Airlines
American Airlines
ORD
9:55a
PWM
3:06p
5h 11m
1 stop
PWM
4:05a
ORD
9:59a
5h 54m
1 stop
Depart: Wed Aug 19 2015 Return: Tue Aug 25 2015 Trip spans 7 days
American Airlines
American Airlines
ORD
8:00a
PWM
3:06p
7h 06m
1 stop
PWM
4:05a
ORD
9:59a
5h 54m
1 stop
Depart: Tue Aug 25 2015 Return: Sat Sep 5 2015 Trip spans 12 days
American Airlines
American Airlines
ORD
9:55a
PWM
3:06p
5h 11m
1 stop
PWM
4:05a
ORD
9:59a
5h 54m
1 stop
Depart: Sat Aug 29 2015 Return: Sat Sep 5 2015 Trip spans 8 days
American Airlines
American Airlines
ORD
9:55a
PWM
3:06p
5h 11m
1 stop
PWM
4:05a
ORD
9:59a
5h 54m
1 stop
Depart: Mon Aug 31 2015 Return: Wed Sep 2 2015 Trip spans 3 days
American Airlines
American Airlines
ORD
9:55a
PWM
3:06p
5h 11m
1 stop
PWM
4:05a
ORD
9:59a
5h 54m
1 stop
Depart: Fri Sep 11 2015 Return: Sun Sep 13 2015 Trip spans 3 days
American Airlines
American Airlines
ORD
7:50a
PWM
3:02p
7h 12m
1 stop
PWM
4:00a
ORD
11:09a
7h 09m
1 stop
Depart: Sat Sep 12 2015 Return: Sun Sep 13 2015 Trip spans 2 days
American Airlines
American Airlines
ORD
4:50a
PWM
10:35a
5h 45m
1 stop
PWM
4:00a
ORD
11:09a
7h 09m
1 stop
Depart: Wed Sep 23 2015 Return: Wed Sep 30 2015 Trip spans 8 days
American Airlines
American Airlines
ORD
1:40a
PWM
8:58a
7h 18m
1 stop
PWM
4:00a
ORD
9:33a
5h 33m
1 stop
Depart: Thu Oct 15 2015 Return: Thu Oct 22 2015 Trip spans 8 days
American Airlines
American Airlines
ORD
7:50a
PWM
3:06p
7h 16m
1 stop
PWM
4:05a
ORD
9:33a
5h 28m
1 stop
Depart: Fri Oct 30 2015 Return: Sun Nov 1 2015 Trip spans 3 days
American Airlines
American Airlines
ORD
7:50a
PWM
3:06p
7h 16m
1 stop
PWM
3:05a
ORD
8:33a
5h 28m
1 stop
Depart: Tue Nov 3 2015 Return: Sat Nov 7 2015 Trip spans 5 days
American Airlines
American Airlines
ORD
6:50a
PWM
2:06p
7h 16m
1 stop
PWM
9:50a
ORD
3:00p
5h 10m
1 stop
Depart: Thu Nov 5 2015 Return: Sun Dec 6 2015 Trip spans 32 days
American Airlines
American Airlines
ORD
9:00a
PWM
2:16p
5h 16m
1 stop
PWM
3:05a
ORD
10:25a
7h 20m
1 stop
Depart: Thu Nov 12 2015 Return: Sun Nov 15 2015 Trip spans 4 days
American Airlines
American Airlines
ORD
7:20a
PWM
2:16p
6h 56m
1 stop
PWM
3:05a
ORD
10:25a
7h 20m
1 stop
Depart: Tue Jul 7 2015 Return: Tue Jul 14 2015 Trip spans 8 days
American Airlines
American Airlines
ORD
9:55a
PWM
3:06p
5h 11m
1 stop
PWM
7:05a
ORD
3:06p
8h 01m
1 stop
Depart: Wed Jul 8 2015 Return: Tue Jul 14 2015 Trip spans 7 days
American Airlines
American Airlines
ORD
9:55a
PWM
3:06p
5h 11m
1 stop
PWM
7:05a
ORD
1:22p
6h 17m
1 stop
Depart: Tue Jul 14 2015 Return: Wed Jul 15 2015 Trip spans 2 days
American Airlines
American Airlines
ORD
9:55a
PWM
3:06p
5h 11m
1 stop
PWM
1:50a
ORD
8:21a
6h 31m
1 stop
Depart: Tue Sep 8 2015 Return: Mon Sep 14 2015 Trip spans 7 days
US Airways
US Airways
ORD
12:50p
PWM
5:36p
4h 46m
1 stop
PWM
2:05p
ORD
6:54p
4h 49m
1 stop
Depart: Sat Nov 7 2015 Return: Wed Nov 11 2015 Trip spans 5 days
Delta
Delta
MDW
11:45a
PWM
3:43p
3h 58m
1 stop
PWM
7:25a
MDW
12:10p
4h 45m
1 stop
Depart: Sat Oct 17 2015 Return: Sun Oct 25 2015 Trip spans 9 days
Delta
Delta
ORD
12:00p
PWM
6:29p
6h 29m
1 stop
PWM
2:50a
ORD
7:21a
4h 31m
1 stop
Depart: Fri Oct 9 2015 Return: Mon Oct 12 2015 Trip spans 4 days
United
United
ORD
4:59a
PWM
7:15a
2h 16m
nonstop
PWM
2:22a
ORD
4:59a
2h 37m
nonstop
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
3486 6:00 am 9:20 am Jul 11 - Jul 18
3486 6:00 am 9:20 am Jul 25 - Jul 25
3486 6:00 am 9:20 am Aug 1 - Aug 1
3486 6:00 am 9:20 am Aug 8 - Aug 8
3644 6:05 am 9:23 am Jul 6 - Aug 17
3551 8:55 am 12:19 pm Jul 7 - Aug 4
3712 8:55 am 12:15 pm Aug 11 - Aug 11
3712 8:59 am 12:19 pm Jul 18 - Jul 31
3712 8:59 am 12:19 pm Jul 6 - Jul 17
3712 8:59 am 12:19 pm Aug 3 - Aug 10
3815 8:59 am 12:23 pm Aug 7 - Aug 7
3823 8:59 am 12:23 pm Aug 12 - Aug 12
5938 8:59 am 12:23 pm Aug 1 - Aug 1
3712 9:04 am 12:24 pm Aug 8 - Aug 8
3712 9:27 am 12:47 pm Aug 9 - Aug 16
3712 9:27 am 12:47 pm Jul 12 - Jul 26
5938 9:27 am 12:51 pm Aug 2 - Aug 2
3917 1:47 pm 5:12 pm Aug 2 - Aug 2
6069 1:47 pm 5:12 pm Jul 25 - Jul 25
6069 1:47 pm 5:12 pm Aug 3 - Aug 10
6069 1:47 pm 5:12 pm Aug 1 - Aug 1
6069 1:47 pm 5:12 pm Jul 21 - Jul 31
6069 1:47 pm 5:12 pm Jul 22 - Jul 29
6069 1:47 pm 5:12 pm Jul 10 - Jul 20
6069 1:47 pm 5:12 pm Aug 4 - Aug 4
6069 1:47 pm 5:12 pm Jul 19 - Jul 19
6069 1:47 pm 5:12 pm Aug 11 - Aug 11
6069 1:47 pm 5:12 pm Aug 12 - Aug 12
6069 1:47 pm 5:12 pm Jul 8 - Jul 15
3540 5:42 pm 9:05 pm Aug 2 - Aug 2
3540 5:42 pm 9:05 pm Jul 26 - Jul 26
3540 5:42 pm 9:05 pm Jul 12 - Jul 12
3540 5:42 pm 9:05 pm Aug 9 - Aug 9
3540 5:42 pm 9:05 pm Aug 5 - Aug 12
3696 5:42 pm 9:01 pm Jul 18 - Aug 1
3696 5:42 pm 9:01 pm Aug 4 - Aug 4
3696 5:42 pm 9:01 pm Aug 8 - Aug 8
5975 5:42 pm 9:05 pm Jul 14 - Jul 21
5975 5:42 pm 9:05 pm Jul 10 - Aug 3
5975 5:42 pm 9:05 pm Jul 19 - Jul 19
5975 5:42 pm 9:05 pm Aug 11 - Aug 16
5975 5:42 pm 9:05 pm Aug 6 - Aug 17
5975 5:42 pm 9:05 pm Jul 28 - Jul 28
Airports
Origin

Chicago
only $339
only $422
Destination

Portland
$339