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.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Portland to Chicago Midway

(Round-trip)
Depart: Sat Oct 28 2017 Return: Sat Nov 4 2017 Trip spans 8 days
Delta
Delta
PDX
12:00a
MDW
8:00a
8h 00m
1 stop
MDW
12:00a
PDX
6:22a
6h 22m
1 stop
Depart: Wed Nov 1 2017 Return: Tue Nov 7 2017 Trip spans 7 days
Delta
Delta
PDX
12:00a
MDW
7:25a
7h 25m
1 stop
MDW
12:00a
PDX
6:38a
6h 38m
1 stop
Depart: Sat Jan 20 2018 Return: Wed Jan 24 2018 Trip spans 5 days
Delta
Delta
PDX
12:00a
MDW
7:30a
7h 30m
1 stop
MDW
12:00a
PDX
8:48a
8h 48m
1 stop
Depart: Fri Dec 1 2017 Return: Sat Dec 2 2017 Trip spans 2 days
Delta
Delta
PDX
12:00a
MDW
6:12a
6h 12m
1 stop
MDW
12:00a
PDX
6:31a
6h 31m
1 stop
Depart: Sat Feb 3 2018 Return: Wed Feb 7 2018 Trip spans 5 days
Delta
Delta
PDX
12:00a
MDW
5:30a
5h 30m
1 stop
MDW
12:00a
PDX
6:06a
6h 06m
1 stop
Depart: Mon Oct 23 2017 Return: Sat Oct 28 2017 Trip spans 6 days
Delta
Delta
PDX
12:00a
MDW
9:35a
9h 35m
1 stop
MDW
12:00a
PDX
9:01a
9h 01m
1 stop
Depart: Sat Sep 30 2017 Return: Tue Oct 3 2017 Trip spans 4 days
Delta
Delta
PDX
12:00a
MDW
5:49a
5h 49m
1 stop
MDW
12:00a
PDX
6:33a
6h 33m
1 stop
Depart: Sun Dec 24 2017 Return: Sat Jan 6 2018 Trip spans 14 days
Delta
Delta
PDX
12:00a
MDW
6:34a
6h 34m
1 stop
MDW
12:00a
PDX
6:06a
6h 06m
1 stop
Depart: Tue Nov 7 2017 Return: Mon Nov 13 2017 Trip spans 7 days
Delta
Delta
PDX
12:00a
MDW
7:40a
7h 40m
1 stop
MDW
12:00a
PDX
8:25a
8h 25m
1 stop
Depart: Thu Mar 1 2018 Return: Mon Mar 5 2018 Trip spans 5 days
Delta
Delta
PDX
12:00a
MDW
8:40a
8h 40m
1 stop
MDW
12:00a
PDX
8:48a
8h 48m
1 stop
Depart: Fri Sep 22 2017 Return: Sun Sep 24 2017 Trip spans 3 days
Delta
Delta
PDX
12:00a
MDW
9:04a
9h 04m
1 stop
MDW
12:00a
PDX
8:53a
8h 53m
1 stop
Depart: Tue Nov 21 2017 Return: Fri Nov 24 2017 Trip spans 4 days
Delta
Delta
PDX
12:00a
MDW
6:06a
6h 06m
1 stop
MDW
12:00a
PDX
9:13a
9h 13m
2 stops
Depart: Sun Dec 24 2017 Return: Fri Dec 29 2017 Trip spans 6 days
Delta
Delta
PDX
12:00a
MDW
6:34a
6h 34m
1 stop
MDW
12:00a
PDX
8:19a
8h 19m
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
1485 6:00 am 11:55 am Oct 2 - Oct 30
268 6:15 am 12:15 pm Sep 5 - Sep 29
1293 6:50 am 12:50 pm Sep 30 - Sep 30
4789 6:55 am 12:50 pm Oct 7 - Oct 28
4309 7:10 am 1:10 pm Oct 29 - Oct 29
4309 7:10 am 1:10 pm Oct 1 - Oct 1
4309 7:10 am 1:10 pm Oct 8 - Oct 22
1414 1:55 pm 7:55 pm Sep 30 - Sep 30
3483 1:55 pm 7:50 pm Oct 7 - Oct 28
5619 2:45 pm 8:40 pm Oct 1 - Oct 29
5564 3:00 pm 8:55 pm Sep 5 - Sep 29
1801 3:05 pm 9:00 pm Oct 2 - Nov 3
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

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

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

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.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Portland
$200
Destination

Chicago
$200
Airlines