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Find Deals on Flights from Chicago Midway to Portland (MDW - PDX)

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

Book cheap flights from Chicago Midway to Portland

(Round-trip)
Depart: Tue Sep 1 2015 Return: Sat Sep 19 2015 Trip spans 19 days
Delta
Delta
MDW
7:06a
PDX
2:43p
7h 37m
1 stop
PDX
12:42p
MDW
6:06p
5h 24m
1 stop
Depart: Wed Sep 2 2015 Return: Wed Sep 16 2015 Trip spans 15 days
Delta
Delta
MDW
9:50a
PDX
7:49p
9h 59m
1 stop
PDX
9:39a
MDW
6:06p
8h 27m
1 stop
Depart: Wed Sep 9 2015 Return: Tue Sep 15 2015 Trip spans 7 days
Delta
Delta
MDW
8:25a
PDX
4:48p
8h 23m
1 stop
PDX
9:39a
MDW
6:06p
8h 27m
1 stop
Depart: Sat Sep 12 2015 Return: Sat Sep 19 2015 Trip spans 8 days
Delta
Delta
MDW
2:35a
PDX
8:41a
6h 06m
1 stop
PDX
12:42p
MDW
6:06p
5h 24m
1 stop
Depart: Tue Sep 15 2015 Return: Sat Sep 19 2015 Trip spans 5 days
Delta
Delta
MDW
11:11a
PDX
5:05p
5h 54m
1 stop
PDX
12:42p
MDW
6:06p
5h 24m
1 stop
Depart: Wed Sep 16 2015 Return: Sat Sep 19 2015 Trip spans 4 days
Delta
Delta
MDW
2:30a
PDX
10:15a
7h 45m
1 stop
PDX
9:39a
MDW
6:06p
8h 27m
1 stop
Depart: Fri Sep 18 2015 Return: Sat Sep 26 2015 Trip spans 9 days
Delta
Delta
MDW
2:30a
PDX
10:15a
7h 45m
1 stop
PDX
2:20a
MDW
11:22a
9h 02m
1 stop
Depart: Tue Sep 22 2015 Return: Tue Sep 29 2015 Trip spans 8 days
Delta
Delta
MDW
8:58a
PDX
2:43p
5h 45m
1 stop
PDX
2:55a
MDW
8:41a
5h 46m
1 stop
Depart: Wed Sep 23 2015 Return: Mon Sep 28 2015 Trip spans 6 days
Delta
Delta
MDW
8:25a
PDX
4:48p
8h 23m
1 stop
PDX
6:55p
MDW
2:42a
7h 47m
1 stop
Depart: Fri Sep 25 2015 Return: Mon Sep 28 2015 Trip spans 4 days
Delta
Delta
MDW
7:06a
PDX
2:43p
7h 37m
1 stop
PDX
6:55p
MDW
2:42a
7h 47m
1 stop
Depart: Sat Sep 26 2015 Return: Thu Oct 1 2015 Trip spans 6 days
Delta
Delta
MDW
2:35a
PDX
8:41a
6h 06m
1 stop
PDX
12:43p
MDW
6:07p
5h 24m
1 stop
Depart: Mon Sep 28 2015 Return: Fri Oct 2 2015 Trip spans 5 days
Delta
Delta
MDW
2:30a
PDX
10:15a
7h 45m
1 stop
PDX
6:55p
MDW
2:48a
7h 53m
1 stop
Depart: Wed Sep 30 2015 Return: Mon Oct 5 2015 Trip spans 6 days
Delta
Delta
MDW
8:25a
PDX
4:48p
8h 23m
1 stop
PDX
6:55p
MDW
2:48a
7h 53m
1 stop
Depart: Sat Oct 3 2015 Return: Mon Oct 5 2015 Trip spans 3 days
Delta
Delta
MDW
2:30a
PDX
10:19a
7h 49m
1 stop
PDX
6:55p
MDW
2:48a
7h 53m
1 stop
Depart: Tue Oct 6 2015 Return: Sat Oct 10 2015 Trip spans 5 days
Delta
Delta
MDW
8:50a
PDX
2:46p
5h 56m
1 stop
PDX
12:43p
MDW
6:07p
5h 24m
1 stop
Depart: Sat Oct 10 2015 Return: Wed Oct 14 2015 Trip spans 5 days
Delta
Delta
MDW
2:30a
PDX
10:19a
7h 49m
1 stop
PDX
12:43p
MDW
6:07p
5h 24m
1 stop
Depart: Wed Oct 14 2015 Return: Mon Oct 19 2015 Trip spans 6 days
Delta
Delta
MDW
2:30a
PDX
10:19a
7h 49m
1 stop
PDX
6:55p
MDW
2:48a
7h 53m
1 stop
Depart: Fri Oct 16 2015 Return: Mon Oct 19 2015 Trip spans 4 days
Delta
Delta
MDW
2:30a
PDX
10:19a
7h 49m
1 stop
PDX
6:55p
MDW
2:48a
7h 53m
1 stop
Depart: Sat Oct 17 2015 Return: Wed Oct 21 2015 Trip spans 5 days
Delta
Delta
MDW
8:30a
PDX
4:52p
8h 22m
1 stop
PDX
12:43p
MDW
6:07p
5h 24m
1 stop
Depart: Sun Oct 18 2015 Return: Tue Oct 20 2015 Trip spans 3 days
Delta
Delta
MDW
2:30a
PDX
10:19a
7h 49m
1 stop
PDX
12:43p
MDW
6:07p
5h 24m
1 stop
Select an airline:  Southwest
Direct flights MDW to PDX on Southwest
Flight # Depart MDW Arrive PDX Sun Mon Tue Wed Thu Fri Sat Valid Between
2425 8:15 am 10:35 am Jul 10 - Aug 7
2425 8:15 am 10:35 am Jun 28 - Aug 2
2425 8:15 am 10:35 am Jun 29 - Jul 9
2014 8:40 am 11:05 am Jul 11 - Aug 8
3763 12:35 pm 2:55 pm Jun 28 - Aug 7
1315 3:00 pm 5:20 pm Jul 11 - Aug 8
4513 7:15 pm 9:35 pm Jul 11 - Aug 1
4554 8:00 pm 10:25 pm Jun 28 - Aug 2
4213 8:05 pm 10:30 pm Jul 10 - Aug 7
4213 8:05 pm 10:30 pm Jun 29 - Jul 9
Airports
Origin

Chicago
$294
Destination

Portland
$294
Airlines