Find Deals on Flights from Portland to Chicago Midway (PWM - 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: Thu Apr 6 2017 Return: Mon Apr 10 2017 Trip spans 5 days
Delta
Delta
PWM
1:30a
MDW
5:47a
4h 17m
1 stop
MDW
11:52a
PWM
6:50p
6h 58m
1 stop
Depart: Wed Apr 26 2017 Return: Mon May 1 2017 Trip spans 6 days
Delta
Delta
PWM
2:00a
MDW
8:48a
6h 48m
1 stop
MDW
2:40p
PWM
6:55p
4h 15m
1 stop
Depart: Thu Apr 27 2017 Return: Mon May 1 2017 Trip spans 5 days
Delta
Delta
PWM
1:30a
MDW
5:47a
4h 17m
1 stop
MDW
2:40p
PWM
6:55p
4h 15m
1 stop
Depart: Fri Apr 28 2017 Return: Mon May 1 2017 Trip spans 4 days
Delta
Delta
PWM
1:30a
MDW
5:47a
4h 17m
1 stop
MDW
2:40p
PWM
6:55p
4h 15m
1 stop
Depart: Sat Apr 29 2017 Return: Wed May 3 2017 Trip spans 5 days
Delta
Delta
PWM
12:40p
MDW
5:34p
4h 54m
1 stop
MDW
1:00p
PWM
6:55p
5h 55m
1 stop
Depart: Mon May 1 2017 Return: Sat May 6 2017 Trip spans 6 days
Delta
Delta
PWM
1:15p
MDW
7:20p
6h 05m
1 stop
MDW
8:29a
PWM
12:30p
4h 01m
1 stop
Depart: Fri May 5 2017 Return: Tue May 9 2017 Trip spans 5 days
Delta
Delta
PWM
1:15p
MDW
7:20p
6h 05m
1 stop
MDW
10:10a
PWM
6:50p
8h 40m
1 stop
Depart: Sat May 6 2017 Return: Tue May 9 2017 Trip spans 4 days
Delta
Delta
PWM
2:03a
MDW
8:59a
6h 56m
1 stop
MDW
2:40p
PWM
6:55p
4h 15m
1 stop
Depart: Thu May 11 2017 Return: Tue May 16 2017 Trip spans 6 days
Delta
Delta
PWM
1:30a
MDW
5:46a
4h 16m
1 stop
MDW
2:40p
PWM
6:55p
4h 15m
1 stop
Depart: Sat May 13 2017 Return: Tue May 16 2017 Trip spans 4 days
Delta
Delta
PWM
12:40p
MDW
5:34p
4h 54m
1 stop
MDW
2:40p
PWM
6:55p
4h 15m
1 stop
Depart: Tue Jun 6 2017 Return: Tue Jun 13 2017 Trip spans 8 days
Delta
Delta
PWM
2:05a
MDW
10:33a
8h 28m
1 stop
MDW
5:15a
PWM
10:55a
5h 40m
1 stop
Depart: Mon Apr 10 2017 Return: Tue Apr 18 2017 Trip spans 9 days
Delta
Delta
PWM
1:30a
MDW
5:47a
4h 17m
1 stop
MDW
2:45p
PWM
6:45p
4h 00m
1 stop
Depart: Sun Apr 30 2017 Return: Wed May 3 2017 Trip spans 4 days
Delta
Delta
PWM
12:40p
MDW
5:35p
4h 55m
1 stop
MDW
2:40p
PWM
6:55p
4h 15m
1 stop
Depart: Thu May 4 2017 Return: Mon May 8 2017 Trip spans 5 days
Delta
Delta
PWM
1:30a
MDW
5:46a
4h 16m
1 stop
MDW
2:40p
PWM
6:55p
4h 15m
1 stop
Depart: Wed May 24 2017 Return: Wed May 31 2017 Trip spans 8 days
Delta
Delta
PWM
1:30a
MDW
5:46a
4h 16m
1 stop
MDW
2:40p
PWM
6:55p
4h 15m
1 stop
Depart: Thu Jun 1 2017 Return: Tue Jun 6 2017 Trip spans 6 days
Delta
Delta
PWM
1:30a
MDW
5:46a
4h 16m
1 stop
MDW
2:55a
PWM
6:59a
4h 04m
1 stop
Depart: Sat Jun 3 2017 Return: Tue Jun 6 2017 Trip spans 4 days
Delta
Delta
PWM
2:03a
MDW
8:59a
6h 56m
1 stop
MDW
2:55a
PWM
6:59a
4h 04m
1 stop
Depart: Sun May 7 2017 Return: Wed May 10 2017 Trip spans 4 days
Delta
Delta
PWM
1:30a
MDW
8:38a
7h 08m
2 stops
MDW
6:21a
PWM
11:33a
5h 12m
1 stop
Depart: Tue Mar 28 2017 Return: Thu Mar 30 2017 Trip spans 3 days
Delta
Delta
PWM
12:46p
MDW
5:21p
4h 35m
1 stop
MDW
5:22a
PWM
11:11a
5h 49m
1 stop
Depart: Wed Mar 29 2017 Return: Sun Apr 2 2017 Trip spans 5 days
Delta
Delta
PWM
2:00a
MDW
10:07a
8h 07m
1 stop
MDW
2:45p
PWM
6:45p
4h 00m
1 stop
* 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
$260
Destination

Chicago
$260
Airlines