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
Students
under 26
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 Chicago Midway to Portland

(Round-trip)
Depart: Tue Jan 10 2017 Return: Wed Jan 11 2017 Trip spans 2 days
Delta
Delta
MDW
10:29a
PDX
7:35p
9h 06m
1 stop
PDX
6:47a
MDW
3:09p
8h 22m
1 stop
Depart: Thu Dec 8 2016 Return: Mon Dec 12 2016 Trip spans 5 days
Southwest
Southwest
MDW
2:25p
PDX
7:00p
4h 35m
nonstop
PDX
9:40a
MDW
1:35p
3h 55m
nonstop
Depart: Wed Jan 11 2017 Return: Wed Jan 18 2017 Trip spans 8 days
Delta
Delta
MDW
12:26p
PDX
7:31p
7h 05m
1 stop
PDX
1:50a
MDW
9:51a
8h 01m
1 stop
Depart: Sat Jan 14 2017 Return: Sat Jan 28 2017 Trip spans 15 days
Delta
Delta
MDW
12:11p
PDX
7:24p
7h 13m
1 stop
PDX
1:50a
MDW
8:00a
6h 10m
1 stop
Depart: Wed Jan 18 2017 Return: Sat Jan 21 2017 Trip spans 4 days
Delta
Delta
MDW
1:20a
PDX
8:02a
6h 42m
1 stop
PDX
1:50a
MDW
8:00a
6h 10m
1 stop
Depart: Sat Jan 21 2017 Return: Tue Jan 24 2017 Trip spans 4 days
Delta
Delta
MDW
4:00a
PDX
10:14a
6h 14m
1 stop
PDX
9:00a
MDW
3:09p
6h 09m
1 stop
Depart: Tue Jan 24 2017 Return: Sat Jan 28 2017 Trip spans 5 days
Delta
Delta
MDW
1:20a
PDX
8:02a
6h 42m
1 stop
PDX
1:50a
MDW
8:00a
6h 10m
1 stop
Depart: Wed Jan 25 2017 Return: Sat Jan 28 2017 Trip spans 4 days
Delta
Delta
MDW
1:00a
PDX
9:37a
8h 37m
1 stop
PDX
1:50a
MDW
8:00a
6h 10m
1 stop
Depart: Sat Jan 28 2017 Return: Tue Jan 31 2017 Trip spans 4 days
Delta
Delta
MDW
1:00a
PDX
9:34a
8h 34m
1 stop
PDX
1:50a
MDW
9:51a
8h 01m
1 stop
Depart: Tue Feb 7 2017 Return: Tue Feb 14 2017 Trip spans 8 days
Delta
Delta
MDW
1:20a
PDX
8:02a
6h 42m
1 stop
PDX
1:50a
MDW
9:51a
8h 01m
1 stop
Depart: Tue Feb 14 2017 Return: Tue Feb 21 2017 Trip spans 8 days
Delta
Delta
MDW
1:20a
PDX
8:02a
6h 42m
1 stop
PDX
2:00a
MDW
9:40a
7h 40m
1 stop
Depart: Wed Feb 1 2017 Return: Tue Feb 7 2017 Trip spans 7 days
Delta
Delta
MDW
1:20a
PDX
8:02a
6h 42m
1 stop
PDX
1:50a
MDW
7:54a
6h 04m
1 stop
Depart: Mon Jan 9 2017 Return: Tue Jan 10 2017 Trip spans 2 days
Delta
Delta
MDW
10:40a
PDX
7:02p
8h 22m
1 stop
PDX
6:47a
MDW
3:09p
8h 22m
1 stop
Depart: Thu Jan 19 2017 Return: Wed Jan 25 2017 Trip spans 7 days
Delta
Delta
MDW
1:00a
PDX
9:37a
8h 37m
1 stop
PDX
1:50a
MDW
9:50a
8h 00m
1 stop
Depart: Thu Feb 2 2017 Return: Tue Feb 7 2017 Trip spans 6 days
Delta
Delta
MDW
1:00a
PDX
9:37a
8h 37m
1 stop
PDX
1:50a
MDW
7:54a
6h 04m
1 stop
Depart: Fri Feb 3 2017 Return: Tue Feb 7 2017 Trip spans 5 days
Delta
Delta
MDW
1:20a
PDX
8:02a
6h 42m
1 stop
PDX
6:47a
MDW
3:09p
8h 22m
1 stop
Depart: Fri Jan 20 2017 Return: Tue Jan 24 2017 Trip spans 5 days
Delta
Delta
MDW
1:20a
PDX
8:02a
6h 42m
1 stop
PDX
1:50a
MDW
7:54a
6h 04m
1 stop
Depart: Thu Jan 26 2017 Return: Sat Jan 28 2017 Trip spans 3 days
Delta
Delta
MDW
9:08a
PDX
7:02p
9h 54m
1 stop
PDX
1:50a
MDW
8:00a
6h 10m
1 stop
Depart: Fri Jan 27 2017 Return: Sat Jan 28 2017 Trip spans 2 days
Delta
Delta
MDW
12:26p
PDX
7:31p
7h 05m
1 stop
PDX
1:50a
MDW
8:00a
6h 10m
1 stop
Depart: Sat Dec 10 2016 Return: Mon Dec 12 2016 Trip spans 3 days
Delta
Delta
MDW
10:20a
PDX
4:53p
6h 33m
1 stop
PDX
6:00p
MDW
1:44a
7h 44m
1 stop
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
3020 7:55 am 10:25 am Dec 21 - Jan 2
2960 8:20 am 10:50 am Dec 1 - Dec 20
2960 8:20 am 10:50 am Jan 1 - Jan 4
3507 8:20 am 10:50 am Dec 25 - Dec 25
1347 8:40 am 11:10 am Dec 24 - Dec 24
6417 8:40 am 11:10 am Dec 31 - Dec 31
1678 8:50 am 11:25 am Jan 5 - Jan 13
5853 8:50 am 11:25 am Jan 7 - Jan 14
6421 9:50 am 12:20 pm Dec 17 - Dec 17
1341 11:15 am 1:45 pm Dec 24 - Dec 24
2054 6:30 pm 9:05 pm Jan 7 - Mar 4
3948 6:40 pm 9:10 pm Dec 17 - Dec 17
1447 6:55 pm 9:25 pm Dec 24 - Dec 24
6467 6:55 pm 9:25 pm Dec 31 - Dec 31
375 7:25 pm 10:00 pm Jan 1 - Jan 4
375 7:25 pm 10:00 pm Dec 1 - Dec 20
2262 7:30 pm 10:05 pm Dec 25 - Dec 25
2805 7:45 pm 10:25 pm Jan 5 - Feb 13
4908 8:15 pm 10:55 pm Dec 21 - Jan 2
5122 8:15 pm 10:55 pm Jan 8 - Jan 29
* 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

Chicago
$264
Destination

Portland
$264
Airlines Airline reviews

2 travelers who booked a flight from Chicago to Portland rated their chosen airlines with an average of 10.0.

Overall
10.0
Boarding
10.0
Crew
10.0
Comfort
10.0
Food
10.0
Entertainment
10.0