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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: Mon Apr 27 2015 Return: Fri May 8 2015 Trip spans 12 days
JetBlue Airways
JetBlue Airways
PWM
12:01p
ORD
6:20p
6h 19m
1 stop
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
Depart: Tue Apr 28 2015 Return: Fri May 8 2015 Trip spans 11 days
JetBlue Airways
JetBlue Airways
PWM
12:00p
ORD
6:20p
6h 20m
1 stop
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
Depart: Sat May 2 2015 Return: Fri May 8 2015 Trip spans 7 days
JetBlue Airways
JetBlue Airways
PWM
11:00a
ORD
6:35p
7h 35m
1 stop
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
Depart: Mon May 4 2015 Return: Fri May 8 2015 Trip spans 5 days
JetBlue Airways
JetBlue Airways
PWM
11:00a
ORD
6:35p
7h 35m
1 stop
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
Depart: Tue May 5 2015 Return: Fri May 8 2015 Trip spans 4 days
JetBlue Airways
JetBlue Airways
PWM
11:00a
ORD
6:35p
7h 35m
1 stop
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
Depart: Wed May 6 2015 Return: Fri May 8 2015 Trip spans 3 days
JetBlue Airways
JetBlue Airways
PWM
11:00a
ORD
6:35p
7h 35m
1 stop
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
Depart: Fri Apr 24 2015 Return: Fri May 8 2015 Trip spans 15 days
JetBlue Airways
JetBlue Airways
PWM
12:01p
ORD
6:20p
6h 19m
1 stop
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
Depart: Sat Apr 25 2015 Return: Fri May 8 2015 Trip spans 14 days
JetBlue Airways
JetBlue Airways
PWM
11:45a
ORD
6:20p
6h 35m
1 stop
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
Depart: Sun Apr 26 2015 Return: Fri May 8 2015 Trip spans 13 days
JetBlue Airways
JetBlue Airways
PWM
2:00a
ORD
7:56a
5h 56m
1 stop
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
Depart: Wed Apr 29 2015 Return: Fri May 8 2015 Trip spans 10 days
JetBlue Airways
JetBlue Airways
PWM
2:00a
ORD
7:56a
5h 56m
1 stop
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
Depart: Fri May 1 2015 Return: Fri May 8 2015 Trip spans 8 days
JetBlue Airways
JetBlue Airways
PWM
11:00a
ORD
6:35p
7h 35m
1 stop
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
Depart: Thu Apr 30 2015 Return: Fri May 8 2015 Trip spans 9 days
JetBlue Airways
JetBlue Airways
PWM
12:01p
ORD
6:20p
6h 19m
1 stop
ORD
2:00a
PWM
6:57a
4h 57m
1 stop
Depart: Mon Jun 8 2015 Return: Fri Jun 12 2015 Trip spans 5 days
JetBlue Airways
JetBlue Airways
PWM
1:45a
ORD
8:12a
6h 27m
1 stop
ORD
8:20a
PWM
12:42p
4h 22m
1 stop
Depart: Sat May 9 2015 Return: Tue May 19 2015 Trip spans 11 days
American Airlines
American Airlines
PWM
12:20p
ORD
8:25p
8h 05m
1 stop
ORD
2:00a
PWM
5:54a
3h 54m
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
2:00a
PWM
7:45a
5h 45m
1 stop
Depart: Wed Apr 22 2015 Return: Mon May 4 2015 Trip spans 13 days
American Airlines
American Airlines
PWM
7:26a
ORD
11:48a
4h 22m
1 stop
ORD
12:40p
PWM
5:18p
4h 38m
1 stop
Depart: Sun May 3 2015 Return: Tue May 5 2015 Trip spans 3 days
US Airways
US Airways
PWM
8:08a
ORD
1:29p
5h 21m
1 stop
ORD
2:00a
PWM
5:54a
3h 54m
1 stop
Depart: Sat Jul 4 2015 Return: Mon Jul 6 2015 Trip spans 3 days
United
United
PWM
6:09a
ORD
2:53p
8h 44m
2 stops
ORD
9:00a
PWM
5:42p
8h 42m
1 stop
Depart: Fri Aug 21 2015 Return: Tue Aug 25 2015 Trip spans 5 days
Delta
Delta
PWM
7:25a
MDW
2:14p
6h 49m
1 stop
MDW
5:05a
PWM
3:26p
10h 21m
2 stops
Depart: Sat Jun 13 2015 Return: Wed Jun 17 2015 Trip spans 5 days
Delta
Delta
PWM
3:00a
ORD
8:27a
5h 27m
1 stop
ORD
3:00a
PWM
6:50a
3h 50m
1 stop
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
3619 6:17 am 8:00 am Apr 8 - Apr 20
3619 6:17 am 8:00 am Apr 21 - May 5
3619 6:17 am 8:00 am Apr 14 - Apr 14
3619 6:17 am 8:00 am Apr 11 - May 3
3451 6:40 am 8:25 am May 10 - May 10
3619 6:40 am 8:20 am May 6 - May 16
5127 9:52 am 11:40 am Apr 18 - Apr 18
3620 12:46 pm 2:30 pm May 9 - May 30
3620 12:46 pm 2:30 pm May 10 - May 10
3620 1:00 pm 2:44 pm May 6 - May 19
3620 1:02 pm 2:45 pm Apr 12 - Apr 12
3620 1:07 pm 2:50 pm Apr 19 - May 3
3620 1:07 pm 2:50 pm Apr 27 - May 4
3620 1:07 pm 2:50 pm May 5 - May 5
3620 1:07 pm 2:50 pm Apr 9 - Apr 23
3620 1:07 pm 2:50 pm Apr 24 - Apr 24
3620 1:07 pm 2:50 pm Apr 11 - May 2
5938 4:28 pm 6:14 pm Apr 26 - Apr 26
5938 4:28 pm 6:14 pm Apr 27 - May 5
5938 4:28 pm 6:14 pm Apr 7 - Apr 24
6129 4:35 pm 6:19 pm May 10 - May 31
6129 4:35 pm 6:19 pm May 6 - May 21
Airports
Origin

Portland
$228
Destination

Chicago
only $228
only $491