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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 30 2015 Return: Wed Apr 8 2015 Trip spans 10 days
JetBlue Airways
JetBlue Airways
PWM
2:00a
ORD
7:56a
5h 56m
1 stop
ORD
2:30p
PWM
6:56p
4h 26m
1 stop
Depart: Tue Mar 31 2015 Return: Wed Apr 8 2015 Trip spans 9 days
JetBlue Airways
JetBlue Airways
PWM
12:00p
ORD
6:20p
6h 20m
1 stop
ORD
2:30p
PWM
6:56p
4h 26m
1 stop
Depart: Wed Apr 1 2015 Return: Wed Apr 8 2015 Trip spans 8 days
JetBlue Airways
JetBlue Airways
PWM
2:00a
ORD
7:56a
5h 56m
1 stop
ORD
2:30p
PWM
6:56p
4h 26m
1 stop
Depart: Thu Sep 17 2015 Return: Mon Sep 21 2015 Trip spans 5 days
JetBlue Airways
JetBlue Airways
PWM
2:00a
ORD
7:25a
5h 25m
1 stop
ORD
2:25p
PWM
6:58p
4h 33m
1 stop
Depart: Tue Mar 17 2015 Return: Mon Mar 23 2015 Trip spans 7 days
JetBlue Airways
JetBlue Airways
PWM
2:00a
ORD
7:41a
5h 41m
1 stop
ORD
2:32p
PWM
6:57p
4h 25m
1 stop
Depart: Sat Mar 21 2015 Return: Mon Mar 23 2015 Trip spans 3 days
JetBlue Airways
JetBlue Airways
PWM
2:00a
ORD
7:41a
5h 41m
1 stop
ORD
2:32p
PWM
6:57p
4h 25m
1 stop
Depart: Sat Mar 28 2015 Return: Wed Apr 8 2015 Trip spans 12 days
JetBlue Airways
JetBlue Airways
PWM
2:00a
ORD
7:41a
5h 41m
1 stop
ORD
2:30p
PWM
6:56p
4h 26m
1 stop
Depart: Wed Mar 25 2015 Return: Wed Apr 8 2015 Trip spans 15 days
Multiple Airlines
Multiple Airlines
PWM
9:10a
ORD
2:17p
5h 07m
1 stop
ORD
2:30p
PWM
6:56p
4h 26m
1 stop
Depart: Wed Mar 18 2015 Return: Mon Mar 23 2015 Trip spans 6 days
Multiple Airlines
Multiple Airlines
PWM
5:12a
ORD
9:58a
4h 46m
1 stop
ORD
2:32p
PWM
6:57p
4h 25m
1 stop
Depart: Fri Mar 27 2015 Return: Wed Apr 8 2015 Trip spans 13 days
JetBlue Airways
JetBlue Airways
PWM
2:00a
ORD
7:41a
5h 41m
1 stop
ORD
2:30p
PWM
6:56p
4h 26m
1 stop
Depart: Mon Apr 6 2015 Return: Wed Apr 8 2015 Trip spans 3 days
JetBlue Airways
JetBlue Airways
PWM
2:00a
ORD
7:56a
5h 56m
1 stop
ORD
2:30p
PWM
6:56p
4h 26m
1 stop
Depart: Mon Jul 13 2015 Return: Mon Jul 20 2015 Trip spans 8 days
JetBlue Airways
JetBlue Airways
PWM
1:35a
ORD
8:52a
7h 17m
1 stop
ORD
9:12a
PWM
2:20p
5h 08m
1 stop
Depart: Wed Jul 29 2015 Return: Mon Aug 3 2015 Trip spans 6 days
JetBlue Airways
JetBlue Airways
PWM
1:35a
ORD
8:52a
7h 17m
1 stop
ORD
9:12a
PWM
2:20p
5h 08m
1 stop
Depart: Tue Mar 24 2015 Return: Tue Mar 31 2015 Trip spans 8 days
American Airlines
American Airlines
PWM
1:40p
ORD
6:56p
5h 16m
1 stop
ORD
2:00a
PWM
5:54a
3h 54m
1 stop
Depart: Thu Apr 30 2015 Return: Mon May 4 2015 Trip spans 5 days
Multiple Airlines
Multiple Airlines
PWM
2:00a
ORD
7:56a
5h 56m
1 stop
ORD
11:45a
PWM
5:18p
5h 33m
1 stop
Depart: Mon May 4 2015 Return: Wed May 6 2015 Trip spans 3 days
American Airlines
American Airlines
PWM
1:55p
ORD
6:55p
5h 00m
1 stop
ORD
2:00a
PWM
5:54a
3h 54m
1 stop
Depart: Mon Mar 16 2015 Return: Wed Mar 25 2015 Trip spans 10 days
US Airways
US Airways
PWM
1:40p
ORD
6:56p
5h 16m
1 stop
ORD
2:10a
PWM
6:52a
4h 42m
1 stop
Depart: Wed Apr 15 2015 Return: Mon Apr 20 2015 Trip spans 6 days
United
United
PWM
3:47p
ORD
4:40a
12h 53m
1 stop
ORD
3:10p
PWM
4:58a
13h 48m
1 stop
Depart: Wed Apr 22 2015 Return: Tue Apr 28 2015 Trip spans 7 days
Delta
Delta
PWM
3:00a
MDW
10:55a
7h 55m
1 stop
MDW
10:30a
PWM
6:26p
7h 56m
1 stop
Depart: Fri Apr 10 2015 Return: Sun Apr 12 2015 Trip spans 3 days
Delta
Delta
PWM
12:30p
ORD
7:02p
6h 32m
1 stop
ORD
3:00a
PWM
6:58a
3h 58m
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
3469 6:05 am 8:05 am Mar 10 - Mar 10
3470 6:05 am 8:05 am Apr 4 - Apr 4
3470 6:05 am 8:05 am Mar 14 - Mar 21
3504 6:05 am 8:05 am Mar 9 - Mar 13
3504 6:05 am 8:05 am Apr 2 - Apr 6
3504 6:05 am 8:05 am Mar 17 - Mar 31
3550 6:05 am 8:05 am Mar 16 - Mar 30
3550 6:05 am 8:05 am Apr 3 - Apr 3
3554 6:05 am 8:05 am Mar 28 - Mar 28
3619 6:05 am 7:59 am Apr 5 - Apr 5
3621 6:05 am 7:59 am Mar 29 - Mar 29
3634 6:05 am 7:57 am Mar 15 - Mar 22
5939 6:05 am 8:05 am Mar 18 - Apr 1
5939 6:05 am 8:05 am Mar 8 - Mar 11
3459 6:17 am 8:06 am Apr 7 - Apr 7
3619 6:17 am 8:00 am Apr 8 - May 5
3620 1:07 pm 2:50 pm Apr 7 - Apr 23
3508 4:16 pm 6:10 pm Mar 22 - Mar 22
3508 4:16 pm 6:10 pm Mar 8 - Mar 8
3528 4:16 pm 6:10 pm Mar 16 - Apr 2
3550 4:16 pm 6:10 pm Mar 9 - Mar 15
3550 4:16 pm 6:10 pm Apr 6 - Apr 6
3554 4:16 pm 6:10 pm Mar 10 - Mar 10
3573 4:16 pm 6:10 pm Mar 20 - Mar 27
3573 4:16 pm 6:10 pm Apr 3 - Apr 3
3573 4:16 pm 6:10 pm Mar 29 - Mar 29
5938 4:16 pm 6:10 pm Apr 5 - Apr 5
5938 4:28 pm 6:14 pm Apr 7 - Apr 24
Airports
Origin

Portland
$228
Destination

Chicago
only $228
only $406