Find Cheap Flights from Portland to Chicago (PDX - CHI)

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

(Round-trip)
Depart: Tue Aug 29 2017 Return: Tue Sep 5 2017 Trip spans 8 days
United
United
PDX
ORD
3h 53m
nonstop
ORD
PDX
4h 23m
nonstop
Depart: Fri Sep 1 2017 Return: Tue Sep 5 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
PDX
ORD
3h 48m
nonstop
ORD
PDX
4h 23m
nonstop
Depart: Sat Jul 29 2017 Return: Thu Aug 3 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
PDX
ORD
3h 48m
nonstop
ORD
PDX
4h 31m
nonstop
Depart: Tue Jan 9 2018 Return: Tue Jan 16 2018 Trip spans 8 days
Delta
Delta
PDX
MDW
5h 31m
1 stop
MDW
PDX
6h 06m
1 stop
Depart: Fri Sep 1 2017 Return: Tue Sep 5 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
PDX
ORD
3h 48m
nonstop
ORD
PDX
4h 23m
nonstop
Depart: Sun Aug 6 2017 Return: Sun Aug 13 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
PDX
ORD
3h 48m
nonstop
ORD
PDX
4h 31m
nonstop
Depart: Sat Jul 29 2017 Return: Sun Aug 13 2017 Trip spans 16 days
Spirit Airlines
Spirit Airlines
PDX
ORD
3h 48m
nonstop
ORD
PDX
4h 31m
nonstop
Depart: Sat Nov 4 2017 Return: Mon Nov 13 2017 Trip spans 10 days
Multiple Airlines
Multiple Airlines
PDX
ORD
3h 58m
nonstop
ORD
PDX
7h 01m
1 stop
Depart: Wed Aug 2 2017 Return: Mon Aug 7 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
PDX
ORD
3h 48m
nonstop
ORD
PDX
4h 31m
nonstop
Depart: Fri Sep 8 2017 Return: Tue Sep 12 2017 Trip spans 5 days
Delta
Delta
PDX
ORD
6h 27m
1 stop
ORD
PDX
7h 50m
1 stop
Depart: Sat Oct 28 2017 Return: Tue Oct 31 2017 Trip spans 4 days
Multiple Airlines
Multiple Airlines
PDX
ORD
3h 58m
nonstop
ORD
PDX
4h 20m
nonstop
Depart: Thu Oct 26 2017 Return: Mon Oct 30 2017 Trip spans 5 days
United
United
PDX
ORD
4h 01m
nonstop
ORD
PDX
4h 20m
nonstop
Depart: Fri Aug 11 2017 Return: Tue Aug 15 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
PDX
ORD
3h 48m
nonstop
ORD
PDX
4h 31m
nonstop
Depart: Wed Sep 20 2017 Return: Mon Sep 25 2017 Trip spans 6 days
Delta
Delta
PDX
ORD
8h 58m
1 stop
ORD
PDX
7h 49m
1 stop
Depart: Wed Aug 16 2017 Return: Tue Aug 22 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
PDX
ORD
3h 48m
nonstop
ORD
PDX
4h 31m
nonstop
Depart: Fri Oct 20 2017 Return: Wed Oct 25 2017 Trip spans 6 days
Delta
Delta
PDX
MDW
7h 58m
1 stop
MDW
PDX
10h 53m
1 stop
Depart: Sat Nov 4 2017 Return: Fri Nov 10 2017 Trip spans 7 days
Delta
Delta
PDX
ORD
5h 45m
1 stop
ORD
PDX
5h 59m
1 stop
Depart: Tue Nov 14 2017 Return: Wed Nov 22 2017 Trip spans 9 days
Delta
Delta
PDX
ORD
8h 27m
1 stop
ORD
PDX
7h 46m
1 stop
Depart: Mon Dec 25 2017 Return: Tue Jan 9 2018 Trip spans 16 days
Delta
Delta
PDX
ORD
8h 07m
1 stop
ORD
PDX
6h 05m
1 stop
Depart: Tue Nov 21 2017 Return: Fri Nov 24 2017 Trip spans 4 days
United
United
PDX
ORD
7h 09m
1 stop
ORD
PDX
4h 20m
nonstop
Direct flights PDX to CHI on American Airlines
Flight # Depart PDX Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
86 7:00 am 1:00 pm Jul 27 - Aug 21
86 7:00 am 1:02 pm Aug 22 - Oct 4
86 8:00 am 2:00 pm Jul 29 - Aug 19
319 2:35 pm 8:36 pm Aug 1 - Aug 16
319 2:35 pm 8:33 pm Aug 22 - Oct 4
319 2:35 pm 8:33 pm Aug 24 - Sep 4
319 2:35 pm 8:36 pm Jul 22 - Aug 21
2608 11:45 pm 5:35 am Jul 22 - Aug 21
2608 11:59 pm 5:49 am Aug 22 - Sep 5
* 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
$153
Destination

Chicago
only $153
only $200
Airlines Airline reviews

234 travelers who booked a flight from Portland to Chicago rated their chosen airlines with an average of 5.5.

Overall
5.7
Boarding
6.3
Crew
6.3
Comfort
5.1
Food
4.6
Entertainment
4.4