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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 Mar 2 2015 Return: Mon Mar 9 2015 Trip spans 7 days
US Airways
US Airways
PWM
12:40p
ORD
5:56p
5h 16m
1 stop
ORD
3:30a
PWM
7:39a
4h 09m
1 stop
Depart: Wed Mar 4 2015 Return: Sun Mar 8 2015 Trip spans 4 days
Multiple Airlines
Multiple Airlines
PWM
10:33a
ORD
5:19p
6h 46m
1 stop
ORD
3:30a
PWM
7:39a
4h 09m
1 stop
Depart: Wed Apr 1 2015 Return: Wed Apr 8 2015 Trip spans 8 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 Mar 3 2015 Return: Mon Mar 9 2015 Trip spans 6 days
US Airways
US Airways
PWM
12:40p
ORD
5:56p
5h 16m
1 stop
ORD
3:30a
PWM
7:39a
4h 09m
1 stop
Depart: Thu Mar 5 2015 Return: Mon Mar 9 2015 Trip spans 4 days
US Airways
US Airways
PWM
2:00a
ORD
7:13a
5h 13m
1 stop
ORD
3:30a
PWM
7:39a
4h 09m
1 stop
Depart: Fri Mar 6 2015 Return: Mon Mar 9 2015 Trip spans 3 days
US Airways
US Airways
PWM
2:00a
ORD
7:13a
5h 13m
1 stop
ORD
3:30a
PWM
7:39a
4h 09m
1 stop
Depart: Thu Mar 26 2015 Return: Sun Mar 29 2015 Trip spans 4 days
US Airways
US Airways
PWM
3:00a
ORD
9:58a
6h 58m
1 stop
ORD
2:00a
PWM
7:44a
5h 44m
1 stop
Depart: Tue Apr 28 2015 Return: Tue May 5 2015 Trip spans 8 days
Multiple Airlines
Multiple Airlines
PWM
3:00a
ORD
8:10a
5h 10m
1 stop
ORD
2:00a
PWM
6:58a
4h 58m
1 stop
Depart: Sun Feb 8 2015 Return: Tue Feb 10 2015 Trip spans 3 days
American Airlines
American Airlines
PWM
3:06a
ORD
9:00a
5h 54m
1 stop
ORD
4:00a
PWM
10:35a
6h 35m
1 stop
Depart: Mon Feb 9 2015 Return: Tue Feb 10 2015 Trip spans 2 days
American Airlines
American Airlines
PWM
12:09p
ORD
5:59p
5h 50m
1 stop
ORD
4:00a
PWM
10:35a
6h 35m
1 stop
Depart: Sun Mar 1 2015 Return: Mon Mar 9 2015 Trip spans 8 days
US Airways
US Airways
PWM
12:40p
ORD
5:56p
5h 16m
1 stop
ORD
3:30a
PWM
7:39a
4h 09m
1 stop
Depart: Sat Feb 28 2015 Return: Tue Mar 10 2015 Trip spans 10 days
Multiple Airlines
Multiple Airlines
PWM
3:30a
ORD
8:32a
5h 02m
1 stop
ORD
9:55a
PWM
5:07p
7h 12m
1 stop
Depart: Sun Apr 12 2015 Return: Wed Apr 15 2015 Trip spans 4 days
JetBlue Airways
JetBlue Airways
PWM
12:05p
ORD
6:30p
6h 25m
1 stop
ORD
2:24p
PWM
6:57p
4h 33m
1 stop
Depart: Sat Feb 7 2015 Return: Tue Feb 10 2015 Trip spans 4 days
American Airlines
American Airlines
PWM
3:06a
ORD
9:00a
5h 54m
1 stop
ORD
4:00a
PWM
10:35a
6h 35m
1 stop
Depart: Fri Feb 6 2015 Return: Sun Feb 8 2015 Trip spans 3 days
American Airlines
American Airlines
PWM
3:06a
ORD
10:02a
6h 56m
1 stop
ORD
1:00a
PWM
6:39a
5h 39m
1 stop
Depart: Thu Feb 12 2015 Return: Mon Feb 16 2015 Trip spans 5 days
US Airways
US Airways
PWM
8:10a
ORD
1:17p
5h 07m
1 stop
ORD
2:30a
PWM
6:39a
4h 09m
1 stop
Depart: Mon Feb 2 2015 Return: Thu Feb 12 2015 Trip spans 11 days
American Airlines
American Airlines
PWM
12:40p
ORD
6:01p
5h 21m
1 stop
ORD
1:14a
PWM
5:52a
4h 38m
1 stop
Depart: Sat Jan 31 2015 Return: Mon Feb 2 2015 Trip spans 3 days
Delta
Delta
PWM
1:45a
MDW
10:42a
8h 57m
1 stop
MDW
1:35p
PWM
5:42p
4h 07m
1 stop
Depart: Thu Feb 19 2015 Return: Thu Feb 26 2015 Trip spans 8 days
Delta
Delta
PWM
1:45a
ORD
6:45a
5h 00m
1 stop
ORD
5:35a
PWM
9:47a
4h 12m
1 stop
Depart: Wed Mar 11 2015 Return: Sun Mar 15 2015 Trip spans 5 days
United
United
PWM
12:16p
ORD
3:10p
2h 54m
nonstop
ORD
4:35p
PWM
6:46p
2h 11m
nonstop
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
4177 3:15 pm 5:12 pm Jan 24 - Feb 7
3657 3:19 pm 5:10 pm Feb 1 - Feb 1
3655 3:20 pm 5:12 pm Feb 28 - Feb 28
3655 3:20 pm 5:12 pm Feb 14 - Feb 14
3667 3:20 pm 5:12 pm Feb 21 - Feb 21
3657 5:33 pm 7:25 pm Feb 22 - Feb 22
3694 5:33 pm 7:25 pm Feb 12 - Feb 20
3694 5:33 pm 7:25 pm Feb 23 - Mar 4
3657 5:34 pm 7:25 pm Feb 8 - Feb 8
3694 5:34 pm 7:25 pm Jan 19 - Feb 11
Airports
Origin

Portland
$228
Destination

Chicago
only $228
only $324