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
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: Sun Dec 18 2016 Return: Wed Jan 4 2017 Trip spans 18 days
Delta
Delta
PWM
1:00a
MDW
7:45a
6h 45m
1 stop
MDW
11:45a
PWM
4:28p
4h 43m
1 stop
Depart: Mon Dec 19 2016 Return: Wed Jan 4 2017 Trip spans 17 days
Delta
Delta
PWM
1:00a
MDW
7:45a
6h 45m
1 stop
MDW
11:45a
PWM
4:28p
4h 43m
1 stop
Depart: Tue Jan 10 2017 Return: Sat Jan 14 2017 Trip spans 5 days
Delta
Delta
PWM
11:37a
MDW
5:00p
5h 23m
1 stop
MDW
3:45a
PWM
8:25a
4h 40m
1 stop
Depart: Fri Mar 17 2017 Return: Sun Mar 19 2017 Trip spans 3 days
Major Airline
Major Airline
PWM
1:00a
MDW
3:47a
2h 47m
1 stop
MDW
1:00a
PWM
1:47a
0h 47m
1 stop
Depart: Fri Jan 13 2017 Return: Sat Jan 14 2017 Trip spans 2 days
Delta
Delta
PWM
11:37a
MDW
5:00p
5h 23m
1 stop
MDW
3:45a
PWM
8:25a
4h 40m
1 stop
Depart: Sat Dec 17 2016 Return: Sun Dec 18 2016 Trip spans 2 days
Delta
Delta
PWM
1:49a
MDW
8:22a
6h 33m
1 stop
MDW
4:18a
PWM
10:01a
5h 43m
1 stop
Depart: Tue Dec 20 2016 Return: Thu Jan 5 2017 Trip spans 17 days
Delta
Delta
PWM
1:49a
MDW
8:22a
6h 33m
1 stop
MDW
11:45a
PWM
4:28p
4h 43m
1 stop
Depart: Sun Dec 25 2016 Return: Wed Jan 4 2017 Trip spans 11 days
Delta
Delta
PWM
12:45a
MDW
8:19a
7h 34m
1 stop
MDW
11:45a
PWM
4:28p
4h 43m
1 stop
Depart: Sat Jan 14 2017 Return: Mon Jan 16 2017 Trip spans 3 days
Delta
Delta
PWM
11:33a
MDW
4:56p
5h 23m
1 stop
MDW
11:50a
PWM
4:52p
5h 02m
1 stop
Depart: Thu Jan 26 2017 Return: Mon Jan 30 2017 Trip spans 5 days
Delta
Delta
PWM
1:45a
MDW
8:34a
6h 49m
1 stop
MDW
11:50a
PWM
4:52p
5h 02m
1 stop
Depart: Wed Jan 4 2017 Return: Fri Jan 6 2017 Trip spans 3 days
Delta
Delta
PWM
1:45a
MDW
8:22a
6h 37m
1 stop
MDW
10:28a
PWM
4:15p
5h 47m
1 stop
Depart: Sat Jan 7 2017 Return: Mon Jan 9 2017 Trip spans 3 days
Delta
Delta
PWM
12:45a
MDW
9:01a
8h 16m
1 stop
MDW
11:50a
PWM
4:52p
5h 02m
1 stop
Depart: Sun Jan 8 2017 Return: Tue Jan 10 2017 Trip spans 3 days
Delta
Delta
PWM
11:37a
MDW
5:00p
5h 23m
1 stop
MDW
11:50a
PWM
4:52p
5h 02m
1 stop
Depart: Mon Jan 9 2017 Return: Wed Jan 11 2017 Trip spans 3 days
Delta
Delta
PWM
11:37a
MDW
5:00p
5h 23m
1 stop
MDW
11:50a
PWM
4:52p
5h 02m
1 stop
Depart: Wed Jan 25 2017 Return: Sat Jan 28 2017 Trip spans 4 days
Delta
Delta
PWM
11:37a
MDW
5:00p
5h 23m
1 stop
MDW
11:50a
PWM
4:49p
4h 59m
1 stop
Depart: Thu Jan 5 2017 Return: Mon Jan 9 2017 Trip spans 5 days
Delta
Delta
PWM
11:42a
MDW
4:52a
17h 10m
1 stop
MDW
4:15a
PWM
10:02a
5h 47m
1 stop
Depart: Sun Dec 11 2016 Return: Tue Dec 13 2016 Trip spans 3 days
Delta
Delta
PWM
2:00a
MDW
8:19a
6h 19m
1 stop
MDW
11:40a
PWM
4:32p
4h 52m
1 stop
Depart: Mon Dec 12 2016 Return: Tue Dec 13 2016 Trip spans 2 days
Delta
Delta
PWM
11:35a
MDW
4:40p
5h 05m
1 stop
MDW
11:40a
PWM
4:32p
4h 52m
1 stop
Depart: Tue Dec 13 2016 Return: Sat Dec 17 2016 Trip spans 5 days
Delta
Delta
PWM
12:54a
MDW
7:43a
6h 49m
1 stop
MDW
10:28a
PWM
4:15p
5h 47m
1 stop
Depart: Wed Dec 14 2016 Return: Sat Dec 17 2016 Trip spans 4 days
Delta
Delta
PWM
11:35a
MDW
4:40p
5h 05m
1 stop
MDW
10:28a
PWM
4:15p
5h 47m
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
$204
Destination

Chicago
$204
Airlines