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

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Portland to Chicago Midway

(Round-trip)
Depart: Mon Mar 6 2017 Return: Tue Mar 7 2017 Trip spans 2 days
Delta
Delta
PDX
6:15p
MDW
2:53a
8h 38m
1 stop
MDW
10:40a
PDX
7:16p
8h 36m
1 stop
Depart: Sat Mar 18 2017 Return: Sun Mar 19 2017 Trip spans 2 days
Major Airline
Major Airline
PDX
2:00a
MDW
3:29a
1h 29m
nonstop
MDW
2:00a
PDX
7:29a
5h 29m
nonstop
Depart: Tue Mar 7 2017 Return: Mon Mar 13 2017 Trip spans 6 days
Delta
Delta
PDX
8:59a
MDW
3:00p
6h 01m
1 stop
MDW
9:48a
PDX
7:40p
9h 52m
1 stop
Depart: Wed Mar 8 2017 Return: Mon Mar 20 2017 Trip spans 12 days
Delta
Delta
PDX
1:55a
MDW
8:23a
6h 28m
1 stop
MDW
12:35p
PDX
8:23p
7h 48m
1 stop
Depart: Fri Mar 10 2017 Return: Mon Mar 13 2017 Trip spans 3 days
Delta
Delta
PDX
5:35p
MDW
2:43a
9h 08m
1 stop
MDW
12:35p
PDX
8:23p
7h 48m
1 stop
Depart: Sun Apr 23 2017 Return: Tue Apr 25 2017 Trip spans 3 days
Delta
Delta
PDX
8:55p
MDW
5:47a
8h 52m
1 stop
MDW
2:00a
PDX
10:14a
8h 14m
1 stop
Depart: Wed Apr 26 2017 Return: Tue May 2 2017 Trip spans 7 days
Delta
Delta
PDX
8:55p
MDW
5:47a
8h 52m
1 stop
MDW
2:00a
PDX
9:58a
7h 58m
1 stop
Depart: Thu Apr 27 2017 Return: Fri Apr 28 2017 Trip spans 2 days
Delta
Delta
PDX
8:55p
MDW
2:40a
5h 45m
1 stop
MDW
3:46p
PDX
9:48p
6h 02m
1 stop
Depart: Sat Apr 29 2017 Return: Tue May 2 2017 Trip spans 4 days
Delta
Delta
PDX
3:05a
MDW
10:51a
7h 46m
1 stop
MDW
2:00a
PDX
9:58a
7h 58m
1 stop
Depart: Sun Apr 9 2017 Return: Tue Apr 18 2017 Trip spans 10 days
Delta
Delta
PDX
8:55p
MDW
5:47a
8h 52m
1 stop
MDW
11:52a
PDX
7:55p
8h 03m
1 stop
Depart: Wed Apr 12 2017 Return: Tue Apr 18 2017 Trip spans 7 days
Delta
Delta
PDX
8:55p
MDW
4:30a
7h 35m
1 stop
MDW
10:08a
PDX
7:55p
9h 47m
1 stop
Depart: Thu Apr 13 2017 Return: Thu Apr 20 2017 Trip spans 8 days
Delta
Delta
PDX
8:55p
MDW
2:40a
5h 45m
1 stop
MDW
3:46p
PDX
9:48p
6h 02m
1 stop
Depart: Fri Apr 21 2017 Return: Tue Apr 25 2017 Trip spans 5 days
Delta
Delta
PDX
7:00p
MDW
2:47a
7h 47m
1 stop
MDW
2:00a
PDX
10:14a
8h 14m
1 stop
Depart: Sat Apr 22 2017 Return: Tue Apr 25 2017 Trip spans 4 days
Delta
Delta
PDX
3:05a
MDW
10:51a
7h 46m
1 stop
MDW
2:00a
PDX
10:14a
8h 14m
1 stop
Depart: Mon May 1 2017 Return: Tue May 9 2017 Trip spans 9 days
Delta
Delta
PDX
8:45p
MDW
4:36a
7h 51m
1 stop
MDW
1:05p
PDX
9:32p
8h 27m
1 stop
Depart: Fri Jun 2 2017 Return: Mon Jun 12 2017 Trip spans 11 days
Delta
Delta
PDX
7:00p
MDW
3:20a
8h 20m
1 stop
MDW
3:40p
PDX
9:30p
5h 50m
1 stop
Depart: Sat Jun 3 2017 Return: Mon Jun 12 2017 Trip spans 10 days
Delta
Delta
PDX
3:00a
MDW
10:45a
7h 45m
1 stop
MDW
3:40p
PDX
9:30p
5h 50m
1 stop
Depart: Tue Jul 11 2017 Return: Tue Jul 25 2017 Trip spans 15 days
Delta
Delta
PDX
7:39a
MDW
4:15p
8h 36m
1 stop
MDW
9:40a
PDX
8:33p
10h 53m
1 stop
Depart: Mon Jul 31 2017 Return: Mon Aug 7 2017 Trip spans 8 days
Delta
Delta
PDX
8:50p
MDW
5:40a
8h 50m
1 stop
MDW
3:40p
PDX
9:50p
6h 10m
1 stop
Depart: Tue Aug 1 2017 Return: Mon Aug 7 2017 Trip spans 7 days
Delta
Delta
PDX
7:39a
MDW
4:15p
8h 36m
1 stop
MDW
3:40p
PDX
9:50p
6h 10m
1 stop
Select an airline:  Southwest
Direct flights PDX to MDW on Southwest
Flight # Depart PDX Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
1922 6:00 am 12:00 pm Mar 9 - Mar 10
2718 6:20 am 12:20 pm Mar 25 - Apr 22
2718 6:20 am 12:20 pm Mar 18 - Mar 18
2718 6:20 am 12:20 pm Mar 11 - Mar 11
5483 6:20 am 12:15 pm Mar 13 - Mar 17
5483 6:20 am 12:15 pm Mar 20 - Apr 24
4878 6:35 am 12:35 pm Mar 12 - Apr 23
934 6:40 am 12:35 pm Feb 23 - Mar 8
6779 11:00 am 4:55 pm Mar 13 - Mar 13
4081 2:45 pm 8:35 pm Feb 23 - Mar 8
1873 2:55 pm 8:50 pm Mar 13 - Apr 24
1873 2:55 pm 8:50 pm Mar 9 - Mar 10
5299 3:25 pm 9:20 pm Mar 12 - Apr 2
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

Portland
$264
Destination

Chicago
$264
Airlines