Find Cheap Flights to Chicago

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

(Round-trip)
Depart: Tue Sep 19 2017 Return: Tue Sep 26 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
PWM
ORD
4h 47m
1 stop
ORD
PWM
10h 00m
2 stops
Depart: Tue Sep 26 2017 Return: Tue Oct 3 2017 Trip spans 8 days
United
United
PWM
ORD
5h 30m
1 stop
ORD
PWM
7h 40m
2 stops
Depart: Sat Dec 2 2017 Return: Mon Dec 4 2017 Trip spans 3 days
JetBlue
JetBlue
PWM
ORD
6h 08m
1 stop
ORD
PWM
4h 27m
1 stop
Depart: Sat Dec 2 2017 Return: Mon Dec 4 2017 Trip spans 3 days
Delta
Delta
PWM
MDW
9h 26m
2 stops
MDW
PWM
8h 04m
2 stops
Depart: Thu Jul 27 2017 Return: Fri Jul 28 2017 Trip spans 2 days
American Airlines
American Airlines
PWM
ORD
7h 15m
1 stop
ORD
PWM
7h 11m
1 stop
Depart: Wed Oct 11 2017 Return: Wed Oct 18 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
PWM
ORD
5h 26m
1 stop
ORD
PWM
7h 40m
2 stops
Depart: Thu Aug 24 2017 Return: Sat Aug 26 2017 Trip spans 3 days
United
United
PWM
ORD
5h 11m
1 stop
ORD
PWM
13h 58m
1 stop
Depart: Tue Sep 12 2017 Return: Tue Sep 19 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
PWM
ORD
5h 30m
1 stop
ORD
PWM
14h 52m
1 stop
Depart: Tue Sep 12 2017 Return: Mon Sep 18 2017 Trip spans 7 days
United
United
PWM
ORD
5h 30m
1 stop
ORD
PWM
7h 40m
2 stops
Depart: Thu Aug 24 2017 Return: Fri Aug 25 2017 Trip spans 2 days
United
United
PWM
ORD
5h 22m
1 stop
ORD
PWM
24h 40m
1 stop
Depart: Wed Nov 1 2017 Return: Sun Nov 12 2017 Trip spans 12 days
Multiple Airlines
Multiple Airlines
PWM
ORD
6h 47m
1 stop
ORD
PWM
5h 22m
1 stop
Depart: Fri Sep 1 2017 Return: Mon Sep 4 2017 Trip spans 4 days
Delta
Delta
PWM
MDW
4h 35m
1 stop
MDW
PWM
4h 18m
1 stop
Depart: Sat Oct 7 2017 Return: Tue Oct 10 2017 Trip spans 4 days
Delta
Delta
PWM
MDW
4h 36m
1 stop
MDW
PWM
6h 22m
1 stop
Depart: Tue Aug 22 2017 Return: Wed Sep 6 2017 Trip spans 16 days
Delta
Delta
PWM
MDW
7h 13m
2 stops
MDW
PWM
5h 40m
1 stop
Depart: Fri Oct 6 2017 Return: Mon Oct 9 2017 Trip spans 4 days
United
United
PWM
ORD
18h 22m
1 stop
ORD
PWM
8h 45m
2 stops
Depart: Thu Sep 14 2017 Return: Sun Sep 17 2017 Trip spans 4 days
United
United
PWM
ORD
13h 00m
1 stop
ORD
PWM
4h 47m
1 stop
Depart: Wed Aug 23 2017 Return: Mon Aug 28 2017 Trip spans 6 days
Delta
Delta
PWM
MDW
4h 46m
1 stop
MDW
PWM
6h 08m
1 stop
Depart: Tue Oct 3 2017 Return: Sun Oct 8 2017 Trip spans 6 days
Delta
Delta
PWM
MDW
9h 44m
2 stops
MDW
PWM
4h 07m
1 stop
Depart: Tue Sep 12 2017 Return: Mon Sep 18 2017 Trip spans 7 days
Delta
Delta
PWM
MDW
5h 30m
1 stop
MDW
PWM
4h 13m
1 stop
Depart: Thu Sep 14 2017 Return: Sun Sep 17 2017 Trip spans 4 days
Delta
Delta
PWM
MDW
4h 03m
1 stop
MDW
PWM
4h 13m
1 stop
Select an airline:  United
Direct flights PWM to CHI on United
Flight # Depart PWM Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
5739 6:15 am 8:01 am Aug 15 - Sep 3
5739 6:25 am 8:13 am Jul 19 - Aug 14
5513 9:59 am 11:45 am Jul 23 - Aug 13
5817 9:59 am 11:44 am Aug 20 - Aug 27
4568 11:25 am 1:05 pm Aug 15 - Sep 3
4568 11:25 am 1:08 pm Jul 19 - Aug 11
4572 11:25 am 1:08 pm Jul 22 - Aug 13
5667 11:25 am 1:08 pm Aug 14 - Aug 14
5553 1:05 pm 2:50 pm Aug 15 - Aug 19
5553 1:05 pm 2:50 pm Aug 26 - Sep 2
5553 1:05 pm 2:52 pm Jul 19 - Aug 14
5553 1:13 pm 2:53 pm Aug 16 - Sep 5
4219 4:40 pm 6:38 pm Jul 22 - Aug 14
4219 4:40 pm 6:33 pm Aug 15 - Sep 2
4219 5:00 pm 6:58 pm Jul 19 - Aug 11
* 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
$296
Destination

Chicago
only $296
only $342
Airlines Airline reviews

23 travelers who booked a flight from Portland to Chicago rated their chosen airlines with an average of 6.1.

Overall
6.0
Boarding
6.4
Crew
7.1
Comfort
5.5
Food
5.3
Entertainment
6.0