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: Thu Dec 7 2017 Return: Mon Dec 18 2017 Trip spans 12 days
Southwest
Southwest
PDX
12:00a
MDW
3:55a
3h 55m
nonstop
MDW
12:00a
PDX
4:40a
4h 40m
nonstop
Depart: Wed Nov 29 2017 Return: Wed Dec 6 2017 Trip spans 8 days
Delta
Delta
PDX
12:00a
MDW
5:35a
5h 35m
1 stop
MDW
12:00a
PDX
6:45a
6h 45m
1 stop
Depart: Tue Jan 9 2018 Return: Thu Jan 11 2018 Trip spans 3 days
Delta
Delta
PDX
12:00a
MDW
5:26a
5h 26m
1 stop
MDW
12:00a
PDX
6:06a
6h 06m
1 stop
Depart: Thu Feb 8 2018 Return: Tue Feb 13 2018 Trip spans 6 days
Delta
Delta
PDX
12:00a
MDW
7:30a
7h 30m
1 stop
MDW
12:00a
PDX
6:06a
6h 06m
1 stop
Depart: Fri Feb 9 2018 Return: Mon Feb 12 2018 Trip spans 4 days
Delta
Delta
PDX
12:00a
MDW
7:00a
7h 00m
1 stop
MDW
12:00a
PDX
8:29a
8h 29m
1 stop
Depart: Fri Mar 2 2018 Return: Tue Mar 6 2018 Trip spans 5 days
Delta
Delta
PDX
12:00a
MDW
5:53a
5h 53m
1 stop
MDW
12:00a
PDX
6:04a
6h 04m
1 stop
Depart: Tue Apr 3 2018 Return: Sat Apr 7 2018 Trip spans 5 days
Delta
Delta
PDX
12:00a
MDW
5:27a
5h 27m
1 stop
MDW
12:00a
PDX
8:43a
8h 43m
1 stop
Depart: Sun Nov 19 2017 Return: Sat Dec 9 2017 Trip spans 21 days
Delta
Delta
PDX
12:00a
MDW
9:06a
9h 06m
1 stop
MDW
12:00a
PDX
8:55a
8h 55m
1 stop
Depart: Sat Nov 18 2017 Return: Sun Dec 3 2017 Trip spans 16 days
Delta
Delta
PDX
12:00a
MDW
8:05a
8h 05m
1 stop
MDW
12:00a
PDX
8:30a
8h 30m
1 stop
Depart: Sat May 19 2018 Return: Tue May 22 2018 Trip spans 4 days
Delta
Delta
PDX
12:00a
MDW
8:33a
8h 33m
1 stop
MDW
12:00a
PDX
8:24a
8h 24m
1 stop
Depart: Sat Mar 17 2018 Return: Sun Mar 25 2018 Trip spans 9 days
Delta
Delta
PDX
12:00a
MDW
7:40a
7h 40m
1 stop
MDW
12:00a
PDX
8:16a
8h 16m
1 stop
Depart: Tue Dec 26 2017 Return: Tue Jan 2 2018 Trip spans 8 days
Delta
Delta
PDX
12:00a
MDW
7:17a
7h 17m
1 stop
MDW
12:00a
PDX
8:52a
8h 52m
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
1623 5:30 am 11:30 am Nov 28 - Dec 19
6804 5:30 am 11:30 am Nov 26 - Nov 27
6804 5:30 am 11:30 am Nov 24 - Nov 24
6804 5:30 am 11:30 am Dec 25 - Dec 25
6804 5:30 am 11:30 am Dec 20 - Jan 2
2463 6:25 am 12:25 pm Nov 18 - Nov 25
2463 6:25 am 12:25 pm Dec 23 - Dec 30
3196 6:30 am 12:30 pm Dec 3 - Jan 7
2892 7:00 am 1:00 pm Dec 2 - Dec 16
2704 1:55 pm 7:50 pm Dec 2 - Dec 16
5473 3:00 pm 8:55 pm Dec 4 - Dec 19
5473 3:00 pm 8:55 pm Nov 24 - Dec 1
2113 3:05 pm 9:00 pm Dec 23 - Dec 30
2113 3:05 pm 9:00 pm Nov 25 - Nov 25
4339 3:10 pm 9:05 pm Dec 3 - Jan 7
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

Portland
$316
Destination

Chicago
$316