Find Deals on Flights from Chicago Midway to Portland (MDW - PDX)

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

Book cheap flights from Chicago Midway to Portland

(Round-trip)
Depart: Sat Oct 15 2016 Return: Sat Oct 22 2016 Trip spans 8 days
Depart: Thu Nov 3 2016 Return: Sun Nov 6 2016 Trip spans 4 days
Depart: Wed Aug 17 2016 Return: Wed Aug 24 2016 Trip spans 8 days
Depart: Fri Oct 14 2016 Return: Thu Oct 20 2016 Trip spans 7 days
Depart: Sat Aug 20 2016 Return: Tue Aug 23 2016 Trip spans 4 days
Depart: Sat Sep 17 2016 Return: Tue Sep 20 2016 Trip spans 4 days
Depart: Mon Aug 22 2016 Return: Tue Aug 23 2016 Trip spans 2 days
Depart: Thu Oct 6 2016 Return: Sun Oct 9 2016 Trip spans 4 days
Depart: Tue Aug 23 2016 Return: Wed Aug 24 2016 Trip spans 2 days
Depart: Sat Oct 8 2016 Return: Mon Oct 10 2016 Trip spans 3 days
Depart: Wed Aug 24 2016 Return: Tue Aug 30 2016 Trip spans 7 days
Depart: Tue Aug 30 2016 Return: Thu Sep 8 2016 Trip spans 10 days
Depart: Sat Sep 3 2016 Return: Wed Sep 7 2016 Trip spans 5 days
Depart: Wed Sep 14 2016 Return: Wed Sep 21 2016 Trip spans 8 days
Depart: Wed Sep 7 2016 Return: Wed Sep 14 2016 Trip spans 8 days
Depart: Mon Aug 29 2016 Return: Sat Sep 3 2016 Trip spans 6 days
Depart: Thu Sep 8 2016 Return: Sat Sep 10 2016 Trip spans 3 days
Depart: Fri Sep 30 2016 Return: Wed Oct 5 2016 Trip spans 6 days
Depart: Sat Sep 10 2016 Return: Tue Sep 13 2016 Trip spans 4 days
Depart: Tue Sep 13 2016 Return: Tue Sep 20 2016 Trip spans 8 days
Select an airline:  Southwest
Direct flights MDW to PDX on Southwest
Flight # Depart MDW Arrive PDX Sun Mon Tue Wed Thu Fri Sat Valid Between
2890 7:40 am 10:00 am Jul 28 - Aug 5
142 8:15 am 10:35 am Aug 6 - Aug 6
1381 8:30 am 10:50 am Sep 4 - Sep 4
423 8:30 am 10:50 am Sep 5 - Sep 5
423 8:35 am 10:55 am Aug 7 - Sep 2
3244 9:00 am 11:20 am Sep 3 - Sep 3
346 9:00 am 11:20 am Aug 13 - Aug 13
346 9:00 am 11:20 am Aug 20 - Aug 27
2052 3:45 pm 6:05 pm Jul 28 - Aug 5
5007 4:05 pm 6:25 pm Jul 30 - Aug 6
1753 6:10 pm 8:30 pm Jul 30 - Aug 6
2182 6:45 pm 9:00 pm Aug 13 - Oct 1
2648 7:35 pm 9:55 pm Aug 7 - Sep 2
828 7:40 pm 10:00 pm Sep 4 - Sep 4
2648 7:45 pm 10:05 pm Sep 5 - Sep 5
3731 8:45 pm 11:10 pm Jul 30 - Aug 6
3586 9:55 pm 12:15 am Jul 28 - Aug 5
* 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,
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Airports
Origin

Chicago
$200
Destination

Portland
$200