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

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

Book cheap flights from Portland to Chicago

(Round-trip)
Depart: Wed Jun 10 2015 Return: Wed Jun 17 2015 Trip spans 8 days
JetBlue Airways
JetBlue Airways
PWM
1:55a
ORD
8:04a
6h 09m
1 stop
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
Depart: Thu Jun 11 2015 Return: Wed Jun 17 2015 Trip spans 7 days
JetBlue Airways
JetBlue Airways
PWM
1:55a
ORD
8:04a
6h 09m
1 stop
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
Depart: Sat Jun 13 2015 Return: Wed Jun 17 2015 Trip spans 5 days
JetBlue Airways
JetBlue Airways
PWM
1:55a
ORD
8:04a
6h 09m
1 stop
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
Depart: Tue Jun 16 2015 Return: Sun Jun 21 2015 Trip spans 6 days
JetBlue Airways
JetBlue Airways
PWM
1:55a
ORD
8:04a
6h 09m
1 stop
ORD
2:00a
PWM
8:01a
6h 01m
1 stop
Depart: Tue Jul 21 2015 Return: Tue Jul 28 2015 Trip spans 8 days
JetBlue Airways
JetBlue Airways
PWM
1:35a
ORD
9:16a
7h 41m
1 stop
ORD
12:34p
PWM
7:06p
6h 32m
1 stop
Depart: Fri Sep 4 2015 Return: Tue Sep 8 2015 Trip spans 5 days
JetBlue Airways
JetBlue Airways
PWM
1:35a
ORD
8:56a
7h 21m
1 stop
ORD
2:22p
PWM
6:58p
4h 36m
1 stop
Depart: Wed Jun 17 2015 Return: Sun Jun 21 2015 Trip spans 5 days
JetBlue Airways
JetBlue Airways
PWM
1:55a
ORD
8:04a
6h 09m
1 stop
ORD
2:00a
PWM
8:01a
6h 01m
1 stop
Depart: Wed Sep 30 2015 Return: Mon Oct 5 2015 Trip spans 6 days
American Airlines
American Airlines
PWM
4:05a
ORD
9:54a
5h 49m
1 stop
ORD
10:00a
PWM
3:16p
5h 16m
1 stop
Depart: Thu Oct 1 2015 Return: Mon Oct 5 2015 Trip spans 5 days
American Airlines
American Airlines
PWM
4:05a
ORD
9:54a
5h 49m
1 stop
ORD
8:20a
PWM
3:16p
6h 56m
1 stop
Depart: Wed May 27 2015 Return: Wed Jun 10 2015 Trip spans 15 days
American Airlines
American Airlines
PWM
4:05a
ORD
9:57a
5h 52m
1 stop
ORD
3:21a
PWM
7:45a
4h 24m
1 stop
Depart: Tue Jun 9 2015 Return: Wed Jun 10 2015 Trip spans 2 days
American Airlines
American Airlines
PWM
4:05a
ORD
9:59a
5h 54m
1 stop
ORD
9:10a
PWM
2:01p
4h 51m
1 stop
Depart: Tue Jun 2 2015 Return: Wed Jun 10 2015 Trip spans 9 days
American Airlines
American Airlines
PWM
1:59p
ORD
6:55p
4h 56m
1 stop
ORD
9:10a
PWM
2:01p
4h 51m
1 stop
Depart: Wed Jun 3 2015 Return: Wed Jun 10 2015 Trip spans 8 days
American Airlines
American Airlines
PWM
7:26a
ORD
11:48a
4h 22m
1 stop
ORD
2:00a
PWM
5:55a
3h 55m
1 stop
Depart: Tue Jun 23 2015 Return: Tue Jun 30 2015 Trip spans 8 days
American Airlines
American Airlines
PWM
2:05p
ORD
6:56p
4h 51m
1 stop
ORD
1:00p
PWM
6:36p
5h 36m
1 stop
Depart: Wed Jun 24 2015 Return: Tue Jun 30 2015 Trip spans 7 days
American Airlines
American Airlines
PWM
1:03p
ORD
6:03p
5h 00m
1 stop
ORD
1:00p
PWM
6:36p
5h 36m
1 stop
Depart: Tue Jun 30 2015 Return: Sat Jul 4 2015 Trip spans 5 days
American Airlines
American Airlines
PWM
7:25a
ORD
12:02p
4h 37m
1 stop
ORD
9:35a
PWM
2:27p
4h 52m
1 stop
Depart: Fri May 29 2015 Return: Tue Jun 2 2015 Trip spans 5 days
US Airways
US Airways
PWM
7:26a
ORD
12:31p
5h 05m
1 stop
ORD
2:00a
PWM
7:44a
5h 44m
1 stop
Depart: Fri Aug 28 2015 Return: Sun Aug 30 2015 Trip spans 3 days
Delta
Delta
PWM
2:55a
MDW
9:23a
6h 28m
1 stop
MDW
12:33p
PWM
4:52p
4h 19m
1 stop
Depart: Tue Aug 18 2015 Return: Tue Aug 25 2015 Trip spans 8 days
Delta
Delta
PWM
2:55a
ORD
7:41a
4h 46m
1 stop
ORD
6:45a
PWM
10:59a
4h 14m
1 stop
Depart: Thu Jul 9 2015 Return: Tue Jul 14 2015 Trip spans 6 days
United
United
PWM
2:38a
ORD
5:20a
2h 42m
nonstop
ORD
9:47a
PWM
12:12p
2h 25m
nonstop
Select an airline:  United
Direct flights PWM to CHI on United
Flight # Depart PWM Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
3695 6:28 am 8:00 am Jun 28 - Jun 28
3695 6:28 am 8:00 am Jun 17 - Jun 17
3695 6:28 am 8:00 am Jun 7 - Jun 21
4629 6:28 am 8:05 am Jun 5 - Jun 16
4629 6:28 am 8:05 am Jun 6 - Jun 27
4629 6:28 am 8:05 am Jun 18 - Jun 30
5141 6:28 am 8:05 am Jun 4 - Jun 4
3631 6:30 am 8:06 am Jul 2 - Jul 2
3922 6:30 am 8:07 am Jul 1 - Jul 1
3619 6:40 am 8:20 am May 31 - Jun 3
4269 9:43 am 11:25 am Jul 3 - Jul 3
3666 9:58 am 11:35 am Jul 2 - Jul 2
3441 10:11 am 11:53 am Jun 6 - Jun 6
3854 10:19 am 12:01 pm Jun 13 - Jun 13
4162 10:19 am 12:01 pm Jun 27 - Jun 27
4162 10:19 am 12:01 pm Jun 20 - Jun 20
3932 12:58 pm 2:40 pm Jun 20 - Jun 27
3620 1:00 pm 2:44 pm May 28 - Jun 2
3620 1:00 pm 2:44 pm May 29 - Jun 3
3620 1:09 pm 2:46 pm Jun 9 - Jun 23
3620 1:09 pm 2:46 pm Jun 7 - Jun 28
3620 1:09 pm 2:46 pm Jun 5 - Jun 15
3620 1:09 pm 2:46 pm Jun 11 - Jun 18
3620 1:09 pm 2:46 pm Jun 22 - Jun 22
3620 1:09 pm 2:46 pm Jun 29 - Jun 29
3620 1:09 pm 2:46 pm Jun 19 - Jun 26
3620 1:09 pm 2:46 pm Jun 30 - Jun 30
3620 1:09 pm 2:46 pm Jul 1 - Jul 1
3620 1:09 pm 2:46 pm Jun 10 - Jun 24
3620 1:09 pm 2:46 pm Jun 4 - Jun 4
3634 1:22 pm 2:59 pm Jul 3 - Jul 3
3634 1:22 pm 2:59 pm Jul 2 - Jul 9
5130 4:25 pm 6:08 pm Jun 7 - Jun 7
4219 4:29 pm 6:12 pm Jun 17 - Jun 17
4219 4:29 pm 6:12 pm Jun 5 - Jun 5
6129 4:29 pm 6:12 pm Jun 4 - Jun 4
4583 4:34 pm 6:17 pm Jun 19 - Jun 19
5130 4:34 pm 6:17 pm Jun 26 - Jun 29
5130 4:34 pm 6:17 pm Jun 22 - Jun 22
5130 4:34 pm 6:17 pm Jul 1 - Jul 1
5130 4:34 pm 6:17 pm Jun 18 - Jun 25
5130 4:34 pm 6:17 pm Jun 12 - Jun 12
5130 4:34 pm 6:17 pm Jun 9 - Jun 16
5130 4:34 pm 6:17 pm Jun 8 - Jun 8
5130 4:35 pm 6:18 pm Jun 14 - Jun 28
5130 4:35 pm 6:18 pm Jun 30 - Jun 30
6129 4:35 pm 6:19 pm May 29 - Jun 3
4583 4:39 pm 6:22 pm Jun 6 - Jun 6
6129 4:39 pm 6:22 pm Jun 27 - Jun 27
6129 4:39 pm 6:22 pm Jun 13 - Jun 13
4219 4:40 pm 6:20 pm Jul 3 - Jul 3
4219 4:40 pm 6:20 pm Jul 2 - Jul 9
5130 4:44 pm 6:27 pm Jun 20 - Jun 20
Airports
Origin

Portland
$272
Destination

Chicago
only $272
only $524