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
Students
under 26
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 Dec 14 2016 Return: Fri Dec 16 2016 Trip spans 3 days
Major Airline
Major Airline
PDX
12:55a
MDW
8:42p
19h 47m
1 stop
MDW
9:44a
PDX
11:07a
25h 23m
1 stop
Depart: Tue Jan 10 2017 Return: Tue Jan 17 2017 Trip spans 8 days
Delta
Delta
PDX
1:50a
MDW
9:49a
7h 59m
1 stop
MDW
1:20a
PDX
10:20a
9h 00m
1 stop
Depart: Wed Jan 11 2017 Return: Wed Jan 25 2017 Trip spans 15 days
Delta
Delta
PDX
9:00a
MDW
3:09p
6h 09m
1 stop
MDW
1:20a
PDX
8:02a
6h 42m
1 stop
Depart: Tue Mar 7 2017 Return: Tue Apr 18 2017 Trip spans 42 days
Major Airline
Major Airline
PDX
12:55a
MDW
9:29a
8h 34m
1 stop
MDW
3:00a
PDX
12:11p
9h 11m
1 stop
Depart: Sat Jan 21 2017 Return: Wed Jan 25 2017 Trip spans 5 days
Delta
Delta
PDX
1:50a
MDW
8:00a
6h 10m
1 stop
MDW
1:20a
PDX
8:02a
6h 42m
1 stop
Depart: Tue Jan 24 2017 Return: Wed Jan 25 2017 Trip spans 2 days
Delta
Delta
PDX
1:50a
MDW
7:54a
6h 04m
1 stop
MDW
1:20a
PDX
8:02a
6h 42m
1 stop
Depart: Wed Dec 7 2016 Return: Sun Dec 11 2016 Trip spans 5 days
Major Airline
Major Airline
PDX
12:00a
MDW
1:29a
1h 29m
nonstop
MDW
8:00a
PDX
1:29p
5h 29m
nonstop
Depart: Wed Jan 25 2017 Return: Tue Jan 31 2017 Trip spans 7 days
Delta
Delta
PDX
9:00a
MDW
3:09p
6h 09m
1 stop
MDW
1:20a
PDX
8:02a
6h 42m
1 stop
Depart: Tue Dec 6 2016 Return: Mon Dec 12 2016 Trip spans 7 days
Major Airline
Major Airline
PDX
12:00a
MDW
1:29a
1h 29m
nonstop
MDW
8:00a
PDX
1:29p
5h 29m
nonstop
Depart: Sat Jan 28 2017 Return: Tue Jan 31 2017 Trip spans 4 days
Delta
Delta
PDX
1:50a
MDW
8:00a
6h 10m
1 stop
MDW
1:20a
PDX
8:02a
6h 42m
1 stop
Depart: Fri Jan 6 2017 Return: Tue Jan 24 2017 Trip spans 19 days
Delta
Delta
PDX
1:50a
MDW
7:50a
6h 00m
1 stop
MDW
1:20a
PDX
8:02a
6h 42m
1 stop
Depart: Fri Jan 20 2017 Return: Sat Jan 28 2017 Trip spans 9 days
Delta
Delta
PDX
9:00a
MDW
3:09p
6h 09m
1 stop
MDW
12:11p
PDX
7:24p
7h 13m
1 stop
Depart: Mon Jan 30 2017 Return: Tue Jan 31 2017 Trip spans 2 days
Delta
Delta
PDX
9:00a
MDW
3:09p
6h 09m
1 stop
MDW
10:29a
PDX
7:31p
9h 02m
1 stop
Depart: Wed Feb 8 2017 Return: Wed Feb 22 2017 Trip spans 15 days
Delta
Delta
PDX
1:50a
MDW
9:51a
8h 01m
1 stop
MDW
1:25a
PDX
7:56a
6h 31m
1 stop
Depart: Fri Mar 24 2017 Return: Tue Mar 28 2017 Trip spans 5 days
Major Airline
Major Airline
PDX
2:05a
MDW
9:04a
6h 59m
1 stop
MDW
3:00a
PDX
5:39p
14h 39m
1 stop
Depart: Sun Jan 22 2017 Return: Wed Jan 25 2017 Trip spans 4 days
Delta
Delta
PDX
1:50a
MDW
7:54a
6h 04m
1 stop
MDW
1:20a
PDX
8:02a
6h 42m
1 stop
Depart: Mon Jan 23 2017 Return: Wed Jan 25 2017 Trip spans 3 days
Delta
Delta
PDX
1:50a
MDW
7:54a
6h 04m
1 stop
MDW
1:20a
PDX
8:02a
6h 42m
1 stop
Depart: Thu Jan 26 2017 Return: Tue Jan 31 2017 Trip spans 6 days
Delta
Delta
PDX
1:50a
MDW
7:54a
6h 04m
1 stop
MDW
1:20a
PDX
8:02a
6h 42m
1 stop
Depart: Sat Dec 10 2016 Return: Mon Dec 12 2016 Trip spans 3 days
Delta
Delta
PDX
1:40a
MDW
10:21a
8h 41m
1 stop
MDW
10:40a
PDX
6:50p
8h 10m
1 stop
Depart: Sun Dec 11 2016 Return: Thu Dec 15 2016 Trip spans 5 days
Delta
Delta
PDX
2:00a
MDW
7:45a
5h 45m
1 stop
MDW
1:30a
PDX
7:52a
6h 22m
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
5961 6:00 am 11:55 am Dec 21 - Jan 2
6404 6:10 am 12:10 pm Dec 17 - Dec 17
2403 6:20 am 12:15 pm Dec 11 - Dec 20
2403 6:20 am 12:15 pm Jan 1 - Jan 4
3282 6:20 am 12:15 pm Dec 25 - Dec 25
198 6:30 am 12:30 pm Dec 24 - Dec 24
2164 6:30 am 12:30 pm Dec 31 - Dec 31
3191 6:30 am 12:25 pm Jan 7 - Mar 4
934 6:40 am 12:35 pm Jan 5 - Jan 13
4104 1:35 pm 7:30 pm Jan 7 - Mar 4
1936 1:55 pm 7:50 pm Dec 31 - Dec 31
1922 2:00 pm 7:55 pm Dec 17 - Dec 17
1596 2:20 pm 8:15 pm Dec 24 - Dec 24
287 2:40 pm 8:35 pm Jan 1 - Jan 1
287 2:40 pm 8:35 pm Dec 4 - Dec 18
287 2:40 pm 8:35 pm Jan 3 - Jan 4
287 2:40 pm 8:35 pm Dec 1 - Dec 20
4081 2:45 pm 8:35 pm Jan 5 - Feb 13
975 2:45 pm 8:40 pm Dec 25 - Dec 25
1187 3:10 pm 9:00 pm Jan 8 - Jan 29
3934 4:05 pm 10:00 pm Dec 21 - Jan 2
2311 5:30 pm 11:25 pm Dec 24 - Dec 24
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

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Airports
Origin

Portland
$260
Destination

Chicago
$260
Airlines