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Find Flight Deals 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 Apr 21 2015 Return: Thu Apr 23 2015 Trip spans 3 days
Delta
Delta
MDW
2:25a
PDX
8:56a
6h 31m
1 stop
PDX
8:40p
MDW
2:38a
5h 58m
1 stop
Depart: Thu Apr 23 2015 Return: Mon Apr 27 2015 Trip spans 5 days
Delta
Delta
MDW
5:08a
PDX
10:53a
5h 45m
1 stop
PDX
8:40p
MDW
2:38a
5h 58m
1 stop
Depart: Fri Apr 24 2015 Return: Mon Apr 27 2015 Trip spans 4 days
Delta
Delta
MDW
2:25a
PDX
10:53a
8h 28m
1 stop
PDX
7:00p
MDW
2:43a
7h 43m
1 stop
Depart: Tue Apr 28 2015 Return: Thu Apr 30 2015 Trip spans 3 days
Delta
Delta
MDW
7:05a
PDX
2:57p
7h 52m
1 stop
PDX
8:40p
MDW
4:27a
7h 47m
1 stop
Depart: Wed Apr 29 2015 Return: Thu Apr 30 2015 Trip spans 2 days
Delta
Delta
MDW
5:50a
PDX
4:40p
10h 50m
1 stop
PDX
8:40p
MDW
2:38a
5h 58m
1 stop
Depart: Mon May 4 2015 Return: Wed May 6 2015 Trip spans 3 days
Delta
Delta
MDW
12:34p
PDX
8:04p
7h 30m
1 stop
PDX
7:27a
MDW
3:02p
7h 35m
1 stop
Depart: Tue May 5 2015 Return: Wed May 6 2015 Trip spans 2 days
Delta
Delta
MDW
11:12a
PDX
7:01p
7h 49m
1 stop
PDX
8:40p
MDW
2:38a
5h 58m
1 stop
Depart: Wed May 6 2015 Return: Sat May 9 2015 Trip spans 4 days
Delta
Delta
MDW
2:45a
PDX
8:42a
5h 57m
1 stop
PDX
9:05a
MDW
3:35p
6h 30m
1 stop
Depart: Mon May 11 2015 Return: Wed May 13 2015 Trip spans 3 days
Delta
Delta
MDW
12:34p
PDX
8:04p
7h 30m
1 stop
PDX
8:40p
MDW
2:38a
5h 58m
1 stop
Depart: Sat Aug 22 2015 Return: Mon Aug 24 2015 Trip spans 3 days
Delta
Delta
MDW
12:45p
PDX
7:39p
6h 54m
1 stop
PDX
8:50p
MDW
4:30a
7h 40m
1 stop
Depart: Tue Aug 25 2015 Return: Sat Aug 29 2015 Trip spans 5 days
Delta
Delta
MDW
3:30p
PDX
9:28p
5h 58m
1 stop
PDX
6:45p
MDW
2:45a
8h 00m
1 stop
Depart: Sat Aug 29 2015 Return: Sun Sep 6 2015 Trip spans 9 days
Delta
Delta
MDW
1:10p
PDX
9:28p
8h 18m
1 stop
PDX
6:45p
MDW
2:45a
8h 00m
1 stop
Depart: Thu Sep 3 2015 Return: Sun Sep 6 2015 Trip spans 4 days
Delta
Delta
MDW
6:10a
PDX
4:50p
10h 40m
1 stop
PDX
6:45p
MDW
2:45a
8h 00m
1 stop
Depart: Tue Sep 15 2015 Return: Tue Sep 29 2015 Trip spans 15 days
Delta
Delta
MDW
5:05a
PDX
11:02a
5h 57m
1 stop
PDX
6:45p
MDW
2:45a
8h 00m
1 stop
Depart: Wed Apr 22 2015 Return: Tue Apr 28 2015 Trip spans 7 days
Delta
Delta
MDW
7:05a
PDX
4:05p
9h 00m
2 stops
PDX
7:37a
MDW
12:51p
5h 14m
1 stop
Depart: Sat Apr 25 2015 Return: Sat May 2 2015 Trip spans 8 days
Delta
Delta
MDW
11:07a
PDX
9:00p
9h 53m
2 stops
PDX
3:00a
MDW
8:41a
5h 41m
1 stop
Depart: Mon Apr 27 2015 Return: Wed Apr 29 2015 Trip spans 3 days
Delta
Delta
MDW
7:05a
PDX
4:05p
9h 00m
2 stops
PDX
8:40p
MDW
2:38a
5h 58m
1 stop
Depart: Fri May 1 2015 Return: Mon May 4 2015 Trip spans 4 days
Delta
Delta
MDW
12:34p
PDX
9:02p
8h 28m
2 stops
PDX
7:00p
MDW
2:50a
7h 50m
1 stop
Depart: Sat May 2 2015 Return: Mon May 4 2015 Trip spans 3 days
Delta
Delta
MDW
1:09p
PDX
9:01p
7h 52m
2 stops
PDX
7:00p
MDW
2:50a
7h 50m
1 stop
Depart: Sun May 24 2015 Return: Sun May 31 2015 Trip spans 8 days
Delta
Delta
MDW
2:45a
PDX
1:31p
10h 46m
2 stops
PDX
8:40p
MDW
4:27a
7h 47m
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
1902 8:45 am 11:15 am Apr 7 - Apr 7
864 8:45 am 11:15 am Mar 30 - Apr 6
1298 8:50 am 11:15 am Apr 11 - May 16
873 8:50 am 11:15 am Apr 13 - May 22
873 8:50 am 11:15 am Apr 8 - Apr 10
873 8:50 am 11:15 am Apr 12 - May 17
1892 3:35 pm 6:00 pm Apr 5 - Apr 6
2959 3:35 pm 6:00 pm Apr 7 - Apr 7
2023 7:35 pm 10:00 pm Apr 8 - May 22
Airports
Origin

Chicago
$390
Destination

Portland
$390
Airlines