Find Cheap 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.
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: Tue Oct 10 2017 Return: Sat Oct 14 2017 Trip spans 5 days
Delta
Delta
PWM
3:02a
MDW
11:42a
8h 40m
2 stops
MDW
7:30a
PWM
5:28p
9h 58m
2 stops
Depart: Sat Sep 16 2017 Return: Mon Sep 18 2017 Trip spans 3 days
Delta
Delta
PWM
2:00a
MDW
11:24a
9h 24m
2 stops
MDW
12:50p
PWM
6:58p
6h 08m
1 stop
Depart: Thu Nov 9 2017 Return: Mon Nov 13 2017 Trip spans 5 days
Delta
Delta
PWM
12:36a
MDW
7:40a
7h 04m
2 stops
MDW
1:45p
PWM
5:52p
4h 07m
1 stop
Depart: Wed Sep 20 2017 Return: Wed Sep 27 2017 Trip spans 8 days
Delta
Delta
PWM
1:15p
MDW
5:56p
4h 41m
1 stop
MDW
2:45p
PWM
6:58p
4h 13m
1 stop
Depart: Wed Nov 22 2017 Return: Thu Nov 23 2017 Trip spans 2 days
Delta
Delta
PWM
12:15a
MDW
4:38a
4h 23m
1 stop
MDW
7:32a
PWM
11:18a
3h 46m
1 stop
Depart: Thu Sep 7 2017 Return: Sun Sep 10 2017 Trip spans 4 days
Delta
Delta
PWM
1:30a
MDW
8:55a
7h 25m
2 stops
MDW
2:45p
PWM
6:58p
4h 13m
1 stop
Depart: Fri Nov 3 2017 Return: Mon Nov 6 2017 Trip spans 4 days
Delta
Delta
PWM
1:30a
MDW
5:33a
4h 03m
1 stop
MDW
1:30a
PWM
10:35a
9h 05m
2 stops
Depart: Fri Oct 20 2017 Return: Tue Oct 24 2017 Trip spans 5 days
Delta
Delta
PWM
1:30a
MDW
5:33a
4h 03m
1 stop
MDW
3:00a
PWM
6:58a
3h 58m
1 stop
Depart: Fri Sep 15 2017 Return: Mon Sep 18 2017 Trip spans 4 days
Delta
Delta
PWM
1:30a
MDW
5:33a
4h 03m
1 stop
MDW
3:00a
PWM
11:42a
8h 42m
2 stops
Depart: Sat Oct 21 2017 Return: Mon Oct 23 2017 Trip spans 3 days
Delta
Delta
PWM
2:15a
MDW
1:07p
10h 52m
2 stops
MDW
2:45p
PWM
7:02p
4h 17m
1 stop
Depart: Fri Dec 1 2017 Return: Sun Dec 3 2017 Trip spans 3 days
Delta
Delta
PWM
9:25a
MDW
4:12p
6h 47m
2 stops
MDW
11:30a
PWM
5:35p
6h 05m
1 stop
Depart: Thu Sep 21 2017 Return: Sun Sep 24 2017 Trip spans 4 days
Delta
Delta
PWM
3:15a
MDW
11:26a
8h 11m
2 stops
MDW
2:00a
PWM
6:54a
4h 54m
1 stop
Depart: Wed Sep 27 2017 Return: Thu Sep 28 2017 Trip spans 2 days
Delta
Delta
PWM
3:15a
MDW
11:26a
8h 11m
2 stops
MDW
2:00a
PWM
6:54a
4h 54m
1 stop
Depart: Fri Sep 22 2017 Return: Sun Sep 24 2017 Trip spans 3 days
Delta
Delta
PWM
1:30a
MDW
5:33a
4h 03m
1 stop
MDW
12:15p
PWM
6:55p
6h 40m
1 stop
Depart: Fri Sep 29 2017 Return: Sun Oct 1 2017 Trip spans 3 days
Delta
Delta
PWM
1:30a
MDW
5:33a
4h 03m
1 stop
MDW
2:00a
PWM
6:55a
4h 55m
1 stop
Depart: Fri Sep 8 2017 Return: Tue Sep 12 2017 Trip spans 5 days
Delta
Delta
PWM
1:30a
MDW
5:38a
4h 08m
1 stop
MDW
2:45p
PWM
6:58p
4h 13m
1 stop
Depart: Thu Aug 31 2017 Return: Sun Sep 3 2017 Trip spans 4 days
Delta
Delta
PWM
1:30a
MDW
5:33a
4h 03m
1 stop
MDW
12:50p
PWM
5:03p
4h 13m
1 stop
Depart: Fri Sep 1 2017 Return: Mon Sep 4 2017 Trip spans 4 days
Delta
Delta
PWM
1:30a
MDW
5:33a
4h 03m
1 stop
MDW
12:50p
PWM
7:03p
6h 13m
1 stop
Depart: Sat Sep 2 2017 Return: Mon Sep 4 2017 Trip spans 3 days
Delta
Delta
PWM
12:35p
MDW
5:54p
5h 19m
1 stop
MDW
2:45p
PWM
7:03p
4h 18m
1 stop
Depart: Sat Oct 7 2017 Return: Mon Oct 9 2017 Trip spans 3 days
Delta
Delta
PWM
1:30a
MDW
6:10a
4h 40m
1 stop
MDW
2:45p
PWM
7:02p
4h 17m
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
$382
Destination

Chicago
$382
Airlines