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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: Thu Jan 15 2015 Return: Mon Jan 19 2015 Trip spans 5 days
US Airways
US Airways
PWM
2:00a
ORD
7:13a
5h 13m
1 stop
ORD
8:55a
PWM
1:06p
4h 11m
1 stop
Depart: Fri Jan 23 2015 Return: Sun Jan 25 2015 Trip spans 3 days
JetBlue Airways
JetBlue Airways
PWM
1:05a
ORD
6:18a
5h 13m
1 stop
ORD
1:40p
PWM
5:58p
4h 18m
1 stop
Depart: Tue Jan 20 2015 Return: Fri Jan 23 2015 Trip spans 4 days
US Airways
US Airways
PWM
6:23a
ORD
10:55a
4h 32m
1 stop
ORD
8:55a
PWM
4:01p
7h 06m
1 stop
Depart: Wed Mar 25 2015 Return: Sun Mar 29 2015 Trip spans 5 days
JetBlue Airways
JetBlue Airways
PWM
2:00a
ORD
7:22a
5h 22m
1 stop
ORD
2:24p
PWM
7:03p
4h 39m
1 stop
Depart: Fri Jan 16 2015 Return: Tue Jan 20 2015 Trip spans 5 days
Multiple Airlines
Multiple Airlines
PWM
1:05a
ORD
6:18a
5h 13m
1 stop
ORD
8:55a
PWM
4:01p
7h 06m
1 stop
Depart: Tue Jan 6 2015 Return: Wed Jan 14 2015 Trip spans 9 days
JetBlue Airways
JetBlue Airways
PWM
1:05a
ORD
6:18a
5h 13m
1 stop
ORD
1:40p
PWM
5:58p
4h 18m
1 stop
Depart: Thu Jan 8 2015 Return: Sun Jan 11 2015 Trip spans 4 days
US Airways
US Airways
PWM
2:00a
ORD
8:58a
6h 58m
1 stop
ORD
1:00a
PWM
6:35a
5h 35m
1 stop
Depart: Wed Mar 4 2015 Return: Tue Mar 10 2015 Trip spans 6 days
JetBlue Airways
JetBlue Airways
PWM
10:33a
ORD
5:16p
6h 43m
1 stop
ORD
2:35p
PWM
6:59p
4h 24m
1 stop
Depart: Sun Jan 11 2015 Return: Wed Jan 14 2015 Trip spans 4 days
American Airlines
American Airlines
PWM
3:45a
ORD
9:00a
5h 15m
1 stop
ORD
7:15a
PWM
2:01p
6h 46m
1 stop
Depart: Thu Dec 25 2014 Return: Thu Jan 1 2015 Trip spans 8 days
US Airways
US Airways
PWM
12:45a
ORD
5:40a
4h 55m
1 stop
ORD
4:45a
PWM
11:06a
6h 21m
1 stop
Depart: Fri Dec 26 2014 Return: Thu Jan 1 2015 Trip spans 7 days
Multiple Airlines
Multiple Airlines
PWM
7:25a
ORD
1:52p
6h 27m
1 stop
ORD
4:45a
PWM
11:06a
6h 21m
1 stop
Depart: Sat May 30 2015 Return: Mon Jun 8 2015 Trip spans 10 days
Multiple Airlines
Multiple Airlines
PWM
2:00a
ORD
8:11a
6h 11m
1 stop
ORD
12:10p
PWM
5:04p
4h 54m
1 stop
Depart: Thu Jan 1 2015 Return: Fri Jan 2 2015 Trip spans 2 days
US Airways
US Airways
PWM
12:40p
ORD
5:52p
5h 12m
1 stop
ORD
12:15p
PWM
5:47p
5h 32m
1 stop
Depart: Sun May 3 2015 Return: Fri May 8 2015 Trip spans 6 days
Multiple Airlines
Multiple Airlines
PWM
3:00a
ORD
8:10a
5h 10m
1 stop
ORD
2:00a
PWM
9:39a
7h 39m
1 stop
Depart: Fri Mar 20 2015 Return: Sun Mar 29 2015 Trip spans 10 days
JetBlue Airways
JetBlue Airways
PWM
11:34a
ORD
6:16p
6h 42m
1 stop
ORD
2:24p
PWM
7:03p
4h 39m
1 stop
Depart: Thu Apr 9 2015 Return: Mon Apr 13 2015 Trip spans 5 days
JetBlue Airways
JetBlue Airways
PWM
2:00a
ORD
7:50a
5h 50m
1 stop
ORD
2:24p
PWM
6:57p
4h 33m
1 stop
Depart: Tue Dec 30 2014 Return: Thu Jan 1 2015 Trip spans 3 days
Multiple Airlines
Multiple Airlines
PWM
6:25a
ORD
11:45a
5h 20m
1 stop
ORD
4:45a
PWM
11:06a
6h 21m
1 stop
Depart: Mon May 4 2015 Return: Sat May 9 2015 Trip spans 6 days
United
United
PWM
8:54a
ORD
5:59p
9h 05m
2 stops
ORD
10:30a
PWM
5:42p
7h 12m
2 stops
Depart: Fri Jan 2 2015 Return: Sun Jan 4 2015 Trip spans 3 days
Delta
Delta
PWM
11:40a
MDW
4:14p
4h 34m
1 stop
MDW
2:15a
PWM
6:00a
3h 45m
1 stop
Depart: Wed Dec 31 2014 Return: Sat Jan 3 2015 Trip spans 4 days
Delta
Delta
PWM
12:25a
ORD
5:28a
5h 03m
1 stop
ORD
3:55a
PWM
10:14a
6h 19m
1 stop
Change your search
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
3645 7:06 am 8:57 am Dec 29 - Jan 5
3645 7:06 am 8:57 am Dec 31 - Dec 31
3657 7:06 am 8:57 am Jan 3 - Jan 4
3695 7:06 am 8:57 am Jan 6 - Jan 6
3714 7:06 am 8:57 am Dec 21 - Dec 28
3657 9:15 am 11:05 am Jan 1 - Jan 1
6069 11:41 am 1:37 pm Jan 3 - Jan 3
3616 11:45 am 1:35 pm Dec 28 - Dec 28
3695 11:45 am 1:35 pm Dec 29 - Jan 5
4177 3:15 pm 5:12 pm Jan 10 - Feb 7
3667 5:27 pm 7:15 pm Dec 26 - Dec 28
3694 5:27 pm 7:15 pm Dec 29 - Jan 5
3694 5:31 pm 7:19 pm Jan 3 - Jan 3
3657 5:34 pm 7:25 pm Jan 11 - Jan 11
3657 5:34 pm 7:25 pm Jan 25 - Jan 25
3694 5:34 pm 7:25 pm Jan 26 - Feb 11
3694 5:34 pm 7:25 pm Jan 6 - Jan 16
3694 5:34 pm 7:25 pm Jan 18 - Jan 23
Airports
Origin

Portland
$228
Destination

Chicago
only $228
only $406