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

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youth
12-17
Child
2-11
Seat Infant
under 2
Lap Infant
under 2
The price shown for each flight will be the average for all passengers including any infants.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

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 16 2015 Return: Wed Sep 23 2015 Trip spans 8 days
Delta
Delta
ORD
6:25a
PWM
11:05a
4h 40m
1 stop
PWM
3:05a
ORD
7:39a
4h 34m
1 stop
Depart: Thu Sep 17 2015 Return: Tue Sep 22 2015 Trip spans 6 days
Delta
Delta
MDW
5:17a
PWM
11:05a
5h 48m
1 stop
PWM
12:40p
MDW
5:27p
4h 47m
1 stop
Depart: Fri Sep 18 2015 Return: Sun Sep 20 2015 Trip spans 3 days
Delta
Delta
ORD
9:59a
PWM
6:42p
8h 43m
1 stop
PWM
3:05a
ORD
7:39a
4h 34m
1 stop
Depart: Sat Sep 19 2015 Return: Tue Sep 29 2015 Trip spans 11 days
Delta
Delta
MDW
11:20a
PWM
6:40p
7h 20m
1 stop
PWM
12:40p
MDW
5:27p
4h 47m
1 stop
Depart: Sun Sep 20 2015 Return: Tue Sep 29 2015 Trip spans 10 days
Delta
Delta
MDW
5:17a
PWM
11:05a
5h 48m
1 stop
PWM
12:40p
MDW
5:27p
4h 47m
1 stop
Depart: Mon Sep 21 2015 Return: Tue Sep 22 2015 Trip spans 2 days
Delta
Delta
MDW
12:35p
PWM
4:32p
3h 57m
1 stop
PWM
3:05a
MDW
9:23a
6h 18m
1 stop
Depart: Tue Sep 22 2015 Return: Tue Sep 29 2015 Trip spans 8 days
Delta
Delta
MDW
12:35p
PWM
4:32p
3h 57m
1 stop
PWM
8:25a
MDW
2:23p
5h 58m
1 stop
Depart: Wed Sep 23 2015 Return: Tue Sep 29 2015 Trip spans 7 days
Delta
Delta
MDW
5:17a
PWM
11:05a
5h 48m
1 stop
PWM
8:25a
MDW
2:23p
5h 58m
1 stop
Depart: Thu Sep 24 2015 Return: Tue Sep 29 2015 Trip spans 6 days
Delta
Delta
MDW
5:55a
PWM
12:06p
6h 11m
1 stop
PWM
8:25a
MDW
3:40p
7h 15m
1 stop
Depart: Fri Sep 25 2015 Return: Tue Sep 29 2015 Trip spans 5 days
Delta
Delta
MDW
11:20a
PWM
6:42p
7h 22m
1 stop
PWM
12:40p
MDW
5:27p
4h 47m
1 stop
Depart: Sat Sep 26 2015 Return: Wed Sep 30 2015 Trip spans 5 days
Delta
Delta
MDW
12:35p
PWM
4:30p
3h 55m
1 stop
PWM
8:27a
MDW
12:59p
4h 32m
1 stop
Depart: Sun Sep 27 2015 Return: Wed Sep 30 2015 Trip spans 4 days
Delta
Delta
MDW
5:17a
PWM
11:05a
5h 48m
1 stop
PWM
2:50a
MDW
8:50a
6h 00m
1 stop
Depart: Mon Sep 28 2015 Return: Tue Sep 29 2015 Trip spans 2 days
Delta
Delta
MDW
12:35p
PWM
4:32p
3h 57m
1 stop
PWM
12:40p
MDW
5:27p
4h 47m
1 stop
Depart: Tue Sep 29 2015 Return: Wed Sep 30 2015 Trip spans 2 days
Delta
Delta
MDW
12:35p
PWM
4:32p
3h 57m
1 stop
PWM
12:40p
MDW
5:27p
4h 47m
1 stop
Depart: Wed Sep 30 2015 Return: Thu Oct 1 2015 Trip spans 2 days
Delta
Delta
MDW
5:17a
PWM
11:05a
5h 48m
1 stop
PWM
8:30a
MDW
12:52p
4h 22m
1 stop
Depart: Thu Oct 1 2015 Return: Sun Oct 4 2015 Trip spans 4 days
Delta
Delta
ORD
5:08a
PWM
11:15a
6h 07m
1 stop
PWM
2:50a
ORD
7:36a
4h 46m
1 stop
Depart: Tue Sep 15 2015 Return: Wed Sep 23 2015 Trip spans 9 days
American Airlines
American Airlines
ORD
9:45a
PWM
3:02p
5h 17m
1 stop
PWM
10:20a
ORD
4:39p
6h 19m
1 stop
Depart: Wed Oct 7 2015 Return: Tue Oct 13 2015 Trip spans 7 days
JetBlue Airways
JetBlue Airways
ORD
3:00a
PWM
7:50a
4h 50m
1 stop
PWM
11:15a
ORD
6:10p
6h 55m
1 stop
Depart: Tue Oct 6 2015 Return: Wed Oct 14 2015 Trip spans 9 days
US Airways
US Airways
ORD
9:45a
PWM
3:06p
5h 21m
1 stop
PWM
4:05a
ORD
9:33a
5h 28m
1 stop
Depart: Thu Jan 7 2016 Return: Mon Jan 11 2016 Trip spans 5 days
United
United
ORD
8:45a
PWM
10:55a
2h 10m
nonstop
PWM
11:22a
ORD
2:04p
2h 42m
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
3644 6:00 am 9:16 am Sep 7 - Sep 13
3644 6:00 am 9:16 am Sep 20 - Sep 20
3644 6:02 am 9:18 am Sep 24 - Oct 24
3644 6:06 am 9:22 am Sep 8 - Sep 21
3644 6:06 am 9:22 am Sep 23 - Sep 23
3652 8:59 am 12:15 pm Sep 27 - Oct 4
3652 8:59 am 12:15 pm Sep 25 - Oct 23
3652 8:59 am 12:15 pm Sep 24 - Oct 22
3652 9:08 am 12:24 pm Oct 11 - Oct 18
3652 9:08 am 12:24 pm Oct 3 - Oct 17
3652 9:08 am 12:24 pm Sep 26 - Sep 26
3633 9:10 am 12:26 pm Sep 19 - Sep 19
3652 9:10 am 12:26 pm Sep 11 - Sep 21
3652 9:10 am 12:26 pm Sep 8 - Sep 15
3652 9:10 am 12:26 pm Sep 10 - Sep 10
3652 9:10 am 12:26 pm Sep 13 - Sep 13
3652 9:10 am 12:26 pm Sep 22 - Sep 22
3652 9:10 am 12:26 pm Sep 20 - Sep 20
3652 9:10 am 12:26 pm Sep 16 - Sep 17
3652 9:10 am 12:26 pm Sep 23 - Sep 23
5137 9:10 am 12:30 pm Sep 12 - Sep 12
6069 1:33 pm 4:58 pm Sep 11 - Sep 11
6069 1:39 pm 5:04 pm Sep 13 - Sep 13
3543 1:40 pm 5:05 pm Sep 24 - Sep 24
6069 1:40 pm 5:05 pm Sep 15 - Sep 15
6069 1:45 pm 5:10 pm Sep 18 - Sep 23
6069 1:45 pm 5:10 pm Sep 10 - Sep 17
3543 1:50 pm 5:15 pm Sep 25 - Oct 23
6069 1:50 pm 5:15 pm Sep 26 - Oct 24
3642 6:00 pm 9:14 pm Sep 19 - Sep 19
3642 6:05 pm 9:21 pm Oct 10 - Oct 17
3642 6:05 pm 9:21 pm Sep 29 - Sep 29
3642 6:10 pm 9:26 pm Oct 6 - Oct 13
3642 6:10 pm 9:26 pm Sep 24 - Oct 5
3642 6:22 pm 9:36 pm Sep 18 - Sep 18
3642 6:22 pm 9:36 pm Sep 3 - Sep 10
3642 6:24 pm 9:38 pm Sep 7 - Sep 14
3642 6:24 pm 9:38 pm Sep 17 - Sep 21
3642 6:25 pm 9:41 pm Oct 11 - Oct 18
3642 6:26 pm 9:42 pm Sep 27 - Oct 4
3642 6:44 pm 9:58 pm Sep 20 - Sep 23
3642 6:44 pm 9:58 pm Sep 9 - Sep 16
3642 6:54 pm 10:08 pm Sep 13 - Sep 13
Airports
Origin

Chicago
only $204
only $204
Destination

Portland
$204