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: Wed Oct 11 2017 Return: Tue Oct 17 2017 Trip spans 7 days
Delta
Delta
PDX
4:45a
MDW
3:03p
10h 18m
1 stop
MDW
8:00a
PDX
4:43p
8h 43m
1 stop
Depart: Sat Jun 3 2017 Return: Mon Jun 5 2017 Trip spans 3 days
Major Airline
Major Airline
PDX
1:00a
MDW
2:29a
1h 29m
nonstop
MDW
9:00a
PDX
2:29p
5h 29m
nonstop
Depart: Tue Oct 24 2017 Return: Sat Oct 28 2017 Trip spans 5 days
Delta
Delta
PDX
8:00a
MDW
2:12p
6h 12m
1 stop
MDW
5:08a
PDX
10:49a
5h 41m
1 stop
Depart: Wed Oct 25 2017 Return: Sat Oct 28 2017 Trip spans 4 days
Delta
Delta
PDX
7:25a
MDW
1:03p
5h 38m
1 stop
MDW
2:30a
PDX
8:41a
6h 11m
1 stop
Depart: Fri Oct 27 2017 Return: Mon Oct 30 2017 Trip spans 4 days
Delta
Delta
PDX
7:20p
MDW
3:18a
7h 58m
1 stop
MDW
12:30p
PDX
8:25p
7h 55m
1 stop
Depart: Fri Nov 3 2017 Return: Tue Nov 7 2017 Trip spans 5 days
Delta
Delta
PDX
7:20p
MDW
3:18a
7h 58m
1 stop
MDW
1:30a
PDX
7:43a
6h 13m
1 stop
Depart: Fri Sep 22 2017 Return: Mon Sep 25 2017 Trip spans 4 days
Delta
Delta
PDX
7:20p
MDW
3:18a
7h 58m
1 stop
MDW
9:10a
PDX
5:48p
8h 38m
1 stop
Depart: Fri Sep 8 2017 Return: Mon Sep 11 2017 Trip spans 4 days
Delta
Delta
PDX
7:20p
MDW
2:48a
7h 28m
1 stop
MDW
12:30p
PDX
8:25p
7h 55m
1 stop
Depart: Fri Oct 13 2017 Return: Tue Oct 17 2017 Trip spans 5 days
Delta
Delta
PDX
7:20p
MDW
3:18a
7h 58m
1 stop
MDW
2:30a
PDX
8:43a
6h 13m
1 stop
Depart: Mon Oct 23 2017 Return: Mon Oct 30 2017 Trip spans 8 days
Delta
Delta
PDX
7:20p
MDW
2:50a
7h 30m
1 stop
MDW
7:07a
PDX
2:20p
7h 13m
1 stop
Depart: Sun Jun 11 2017 Return: Fri Jun 16 2017 Trip spans 6 days
Delta
Delta
PDX
8:40p
MDW
4:39a
7h 59m
1 stop
MDW
3:46p
PDX
9:54p
6h 08m
1 stop
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
3:50p
PDX
9:27p
5h 37m
1 stop
Depart: Fri Jun 9 2017 Return: Mon Jun 12 2017 Trip spans 4 days
Delta
Delta
PDX
7:00p
MDW
3:18a
8h 18m
1 stop
MDW
11:07a
PDX
8:27p
9h 20m
1 stop
Depart: Mon Jun 12 2017 Return: Wed Jun 21 2017 Trip spans 10 days
Delta
Delta
PDX
8:40p
MDW
4:39a
7h 59m
1 stop
MDW
8:55a
PDX
5:46p
8h 51m
1 stop
Depart: Wed Jun 7 2017 Return: Sat Jun 10 2017 Trip spans 4 days
Delta
Delta
PDX
8:45p
MDW
4:29a
7h 44m
1 stop
MDW
11:20a
PDX
5:37p
6h 17m
1 stop
Depart: Thu Jun 8 2017 Return: Mon Jun 12 2017 Trip spans 5 days
Delta
Delta
PDX
8:45p
MDW
4:29a
7h 44m
1 stop
MDW
11:07a
PDX
8:27p
9h 20m
1 stop
Depart: Wed Jun 14 2017 Return: Mon Jun 19 2017 Trip spans 6 days
Delta
Delta
PDX
8:40p
MDW
4:39a
7h 59m
1 stop
MDW
3:46p
PDX
9:54p
6h 08m
1 stop
Depart: Thu Sep 7 2017 Return: Mon Sep 11 2017 Trip spans 5 days
Delta
Delta
PDX
7:25a
MDW
4:15p
8h 50m
1 stop
MDW
12:30p
PDX
8:25p
7h 55m
1 stop
Depart: Fri Sep 15 2017 Return: Wed Sep 20 2017 Trip spans 6 days
Delta
Delta
PDX
7:20p
MDW
3:18a
7h 58m
1 stop
MDW
9:10a
PDX
2:50p
5h 40m
1 stop
Depart: Sat Sep 23 2017 Return: Mon Sep 25 2017 Trip spans 3 days
Delta
Delta
PDX
8:00a
MDW
2:11p
6h 11m
1 stop
MDW
9:10a
PDX
5:48p
8h 38m
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
4403 6:40 am 12:35 pm Jun 4 - Aug 13
2183 6:50 am 12:45 pm Jun 5 - Jun 16
2183 6:50 am 12:45 pm Jun 19 - Aug 14
4561 6:55 am 12:50 pm Jun 24 - Aug 12
4561 6:55 am 12:50 pm Jun 10 - Jun 17
4853 8:30 am 2:25 pm Jun 10 - Aug 12
2977 12:15 pm 6:10 pm Jun 10 - Aug 12
1415 1:05 pm 7:00 pm Jun 5 - Jun 30
1415 1:05 pm 7:00 pm Jul 5 - Aug 14
4431 1:05 pm 7:00 pm Jul 3 - Jul 3
4551 1:05 pm 7:00 pm Jul 4 - Jul 4
2451 1:55 pm 7:50 pm Jun 10 - Aug 12
5218 3:00 pm 8:50 pm Jun 4 - Aug 13
5484 3:10 pm 9:00 pm Jul 3 - Jul 3
1878 3:25 pm 9:15 pm Jun 5 - Jun 30
1878 3:25 pm 9:15 pm Jul 4 - Aug 14
* 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