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: Thu Jun 1 2017 Return: Wed Jun 7 2017 Trip spans 7 days
Major Airline
Major Airline
PDX
ORD
4h 06m
nonstop
ORD
PDX
4h 30m
nonstop
Depart: Wed May 31 2017 Return: Sat Jun 10 2017 Trip spans 11 days
Spirit Airlines
Spirit Airlines
PDX
ORD
3h 54m
nonstop
ORD
PDX
4h 16m
nonstop
Depart: Sat Oct 7 2017 Return: Mon Oct 9 2017 Trip spans 3 days
Frontier
Frontier
PDX
ORD
8h 45m
1 stop
ORD
PDX
8h 50m
1 stop
Depart: Sun Jun 4 2017 Return: Fri Jun 9 2017 Trip spans 6 days
Delta
Delta
PDX
MDW
8h 53m
1 stop
MDW
PDX
7h 45m
1 stop
Depart: Thu Oct 5 2017 Return: Mon Oct 9 2017 Trip spans 5 days
American Airlines
American Airlines
PDX
ORD
7h 50m
1 stop
ORD
PDX
8h 09m
1 stop
Depart: Wed May 3 2017 Return: Tue May 9 2017 Trip spans 7 days
Major Airline
Major Airline
PDX
ORD
3h 55m
nonstop
ORD
PDX
4h 16m
nonstop
Depart: Wed May 31 2017 Return: Thu Jun 1 2017 Trip spans 2 days
Major Airline
Major Airline
PDX
ORD
4h 06m
nonstop
ORD
PDX
4h 16m
nonstop
Depart: Sat Jul 1 2017 Return: Tue Jul 4 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
PDX
ORD
3h 48m
nonstop
ORD
PDX
4h 20m
nonstop
Depart: Wed Jun 7 2017 Return: Sat Jun 10 2017 Trip spans 4 days
Major Airline
Major Airline
PDX
ORD
3h 54m
nonstop
ORD
PDX
4h 30m
nonstop
Depart: Wed May 31 2017 Return: Wed Jun 7 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
PDX
ORD
3h 54m
nonstop
ORD
PDX
4h 16m
nonstop
Depart: Sun Jul 23 2017 Return: Mon Jul 31 2017 Trip spans 9 days
Major Airline
Major Airline
PDX
ORD
3h 48m
nonstop
ORD
PDX
4h 20m
nonstop
Depart: Tue Jul 25 2017 Return: Tue Aug 1 2017 Trip spans 8 days
Major Airline
Major Airline
PDX
ORD
3h 48m
nonstop
ORD
PDX
4h 25m
nonstop
Depart: Tue Jul 4 2017 Return: Mon Jul 10 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
PDX
ORD
3h 48m
nonstop
ORD
PDX
4h 20m
nonstop
Depart: Tue Sep 12 2017 Return: Sat Sep 16 2017 Trip spans 5 days
Delta
Delta
PDX
MDW
8h 50m
1 stop
MDW
PDX
6h 36m
1 stop
Depart: Wed Aug 2 2017 Return: Wed Aug 9 2017 Trip spans 8 days
Major Airline
Major Airline
PDX
ORD
4h 13m
nonstop
ORD
PDX
4h 25m
nonstop
Depart: Wed Aug 30 2017 Return: Mon Sep 4 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
PDX
ORD
3h 48m
nonstop
ORD
PDX
4h 20m
nonstop
Depart: Wed Sep 13 2017 Return: Sat Sep 16 2017 Trip spans 4 days
Delta
Delta
PDX
MDW
6h 12m
1 stop
MDW
PDX
6h 36m
1 stop
Depart: Tue Aug 15 2017 Return: Tue Aug 22 2017 Trip spans 8 days
Major Airline
Major Airline
PDX
ORD
4h 13m
nonstop
ORD
PDX
4h 20m
nonstop
Depart: Fri May 26 2017 Return: Wed May 31 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
PDX
ORD
3h 54m
nonstop
ORD
PDX
4h 16m
nonstop
Depart: Wed May 3 2017 Return: Mon May 8 2017 Trip spans 6 days
Delta
Delta
PDX
MDW
8h 53m
1 stop
MDW
PDX
6h 47m
1 stop
Direct flights PDX to CHI on American Airlines
Flight # Depart PDX Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
86 7:55 am 2:02 pm Apr 29 - May 4
86 7:55 am 2:02 pm May 5 - Jun 1
86 7:55 am 2:02 pm Apr 27 - May 3
319 2:30 pm 8:36 pm May 8 - Jun 1
319 2:30 pm 8:36 pm May 7 - May 28
319 2:30 pm 8:36 pm May 5 - May 31
* 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
$181
Destination

Chicago
only $181
only $324
Airlines Airline reviews

138 travelers who booked a flight from Portland to Chicago rated their chosen airlines with an average of 5.3.

Overall
5.4
Boarding
6.1
Crew
6.0
Comfort
4.7
Food
3.9
Entertainment
3.8