Find Cheap 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: Sun Jun 4 2017 Return: Fri Jun 9 2017 Trip spans 6 days
Delta
Delta
PDX
8:45p
MDW
5:38a
8h 53m
1 stop
MDW
1:52p
PDX
9:37p
7h 45m
1 stop
Depart: Wed May 31 2017 Return: Wed Jun 7 2017 Trip spans 8 days
Major Airline
Major Airline
PDX
2:00a
MDW
3:29a
1h 29m
nonstop
MDW
2:00a
PDX
7:29a
5h 29m
nonstop
Depart: Mon Jun 12 2017 Return: Mon Jun 19 2017 Trip spans 8 days
Delta
Delta
PDX
8:40p
MDW
4:39a
7h 59m
1 stop
MDW
11:07a
PDX
8:27p
9h 20m
1 stop
Depart: Wed Sep 13 2017 Return: Sat Sep 16 2017 Trip spans 4 days
Delta
Delta
PDX
8:00a
MDW
2:12p
6h 12m
1 stop
MDW
1:44a
PDX
8:20a
6h 36m
1 stop
Depart: Fri Sep 15 2017 Return: Tue Sep 19 2017 Trip spans 5 days
Delta
Delta
PDX
7:20p
MDW
3:18a
7h 58m
1 stop
MDW
2:30a
PDX
10:52a
8h 22m
1 stop
Depart: Sat Oct 14 2017 Return: Tue Dec 12 2017 Trip spans 60 days
Delta
Delta
PDX
2:45a
MDW
10:44a
7h 59m
1 stop
MDW
1:30a
PDX
9:52a
8h 22m
1 stop
Depart: Fri May 5 2017 Return: Wed May 10 2017 Trip spans 6 days
Delta
Delta
PDX
7:00p
MDW
3:18a
8h 18m
1 stop
MDW
3:50p
PDX
9:27p
5h 37m
1 stop
Depart: Wed May 10 2017 Return: Fri May 19 2017 Trip spans 10 days
Delta
Delta
PDX
7:00p
MDW
2:46a
7h 46m
1 stop
MDW
3:50p
PDX
9:31p
5h 41m
1 stop
Depart: Fri May 26 2017 Return: Thu Jun 1 2017 Trip spans 7 days
Delta
Delta
PDX
8:45p
MDW
4:27a
7h 42m
1 stop
MDW
1:52p
PDX
9:37p
7h 45m
1 stop
Depart: Fri May 12 2017 Return: Fri May 19 2017 Trip spans 8 days
Delta
Delta
PDX
8:45p
MDW
4:29a
7h 44m
1 stop
MDW
1:00p
PDX
7:47p
6h 47m
1 stop
Depart: Sun May 14 2017 Return: Fri May 19 2017 Trip spans 6 days
Delta
Delta
PDX
8:45p
MDW
5:38a
8h 53m
1 stop
MDW
3:50p
PDX
9:31p
5h 41m
1 stop
Depart: Mon May 1 2017 Return: Thu May 4 2017 Trip spans 4 days
Delta
Delta
PDX
6:55p
MDW
3:46a
8h 51m
1 stop
MDW
2:00a
PDX
10:08a
8h 08m
1 stop
Depart: Tue May 2 2017 Return: Thu May 4 2017 Trip spans 3 days
Delta
Delta
PDX
6:55p
MDW
5:29a
10h 34m
1 stop
MDW
2:00a
PDX
10:08a
8h 08m
1 stop
Depart: Fri Oct 13 2017 Return: Tue Dec 12 2017 Trip spans 61 days
Delta
Delta
PDX
7:20p
MDW
3:18a
7h 58m
1 stop
MDW
1:30a
PDX
7:43a
6h 13m
1 stop
Depart: Tue Apr 25 2017 Return: Tue May 2 2017 Trip spans 8 days
Delta
Delta
PDX
6:55p
MDW
3:37a
8h 42m
1 stop
MDW
11:20a
PDX
5:40p
6h 20m
1 stop
Depart: Thu Apr 27 2017 Return: Tue May 2 2017 Trip spans 6 days
Delta
Delta
PDX
9:47a
MDW
4:11p
6h 24m
1 stop
MDW
11:20a
PDX
5:40p
6h 20m
1 stop
Depart: Tue May 9 2017 Return: Wed May 10 2017 Trip spans 2 days
Delta
Delta
PDX
6:55p
MDW
3:46a
8h 51m
1 stop
MDW
3:50p
PDX
9:27p
5h 37m
1 stop
Depart: Wed May 3 2017 Return: Sat May 6 2017 Trip spans 4 days
Delta
Delta
PDX
9:35a
MDW
4:10p
6h 35m
1 stop
MDW
2:30a
PDX
8:34a
6h 04m
1 stop
Depart: Thu May 4 2017 Return: Mon May 8 2017 Trip spans 5 days
Delta
Delta
PDX
8:45p
MDW
4:29a
7h 44m
1 stop
MDW
1:00p
PDX
7:47p
6h 47m
1 stop
Depart: Sat May 6 2017 Return: Tue May 9 2017 Trip spans 4 days
Delta
Delta
PDX
3:00a
MDW
10:55a
7h 55m
1 stop
MDW
5:10a
PDX
10:55a
5h 45m
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
1844 6:40 am 12:40 pm May 30 - Jun 2
1844 6:40 am 12:40 pm May 29 - May 29
1844 6:40 am 12:40 pm May 9 - May 26
1844 6:40 am 12:40 pm Apr 26 - May 8
4770 6:40 am 12:40 pm May 13 - Jun 3
4770 6:40 am 12:40 pm Apr 29 - May 6
3644 7:15 am 1:15 pm Apr 30 - May 28
1078 2:50 pm 8:50 pm May 28 - May 28
460 2:50 pm 8:50 pm Apr 30 - May 7
460 2:50 pm 8:50 pm May 14 - May 21
792 3:00 pm 9:00 pm Apr 25 - Jun 2
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

Portland
$324
Destination

Chicago
$324
Airlines