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.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Portland to Chicago

(Round-trip)
Depart: Fri Jun 2 2017 Return: Sat Jun 3 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
PDX
ORD
4h 06m
nonstop
ORD
PDX
4h 23m
nonstop
Depart: Wed Jul 12 2017 Return: Wed Jul 19 2017 Trip spans 8 days
Major Airline
Major Airline
PDX
ORD
4h 00m
nonstop
ORD
PDX
4h 25m
nonstop
Depart: Tue Oct 17 2017 Return: Fri Oct 20 2017 Trip spans 4 days
American Airlines
American Airlines
PDX
ORD
4h 02m
nonstop
ORD
PDX
4h 40m
nonstop
Depart: Wed Oct 18 2017 Return: Mon Oct 23 2017 Trip spans 6 days
Delta
Delta
PDX
MDW
8h 50m
1 stop
MDW
PDX
7h 55m
1 stop
Depart: Wed Jun 7 2017 Return: Sun Jun 11 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
PDX
ORD
4h 06m
nonstop
ORD
PDX
4h 23m
nonstop
Depart: Tue Nov 21 2017 Return: Fri Nov 24 2017 Trip spans 4 days
United
United
PDX
ORD
8h 40m
1 stop
ORD
PDX
7h 07m
1 stop
Depart: Mon Jun 12 2017 Return: Mon Jun 19 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
PDX
ORD
4h 06m
nonstop
ORD
PDX
4h 31m
nonstop
Depart: Tue Aug 8 2017 Return: Tue Aug 15 2017 Trip spans 8 days
Major Airline
Major Airline
PDX
ORD
4h 00m
nonstop
ORD
PDX
4h 25m
nonstop
Depart: Wed Aug 9 2017 Return: Tue Aug 15 2017 Trip spans 7 days
Major Airline
Major Airline
PDX
ORD
4h 00m
nonstop
ORD
PDX
4h 31m
nonstop
Depart: Fri Jun 30 2017 Return: Tue Jul 18 2017 Trip spans 19 days
Frontier
Frontier
PDX
ORD
13h 42m
1 stop
ORD
PDX
11h 42m
1 stop
Depart: Wed May 31 2017 Return: Thu Jun 8 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
PDX
ORD
4h 06m
nonstop
ORD
PDX
4h 23m
nonstop
Depart: Tue Jul 11 2017 Return: Wed Jul 19 2017 Trip spans 9 days
Major Airline
Major Airline
PDX
ORD
4h 07m
nonstop
ORD
PDX
4h 31m
nonstop
Depart: Fri Jun 2 2017 Return: Sat Jun 3 2017 Trip spans 2 days
Delta
Delta
PDX
MDW
8h 18m
1 stop
MDW
PDX
7h 43m
1 stop
Depart: Sat May 27 2017 Return: Sat Jun 3 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
PDX
ORD
4h 06m
nonstop
ORD
PDX
4h 23m
nonstop
Depart: Sat Sep 2 2017 Return: Wed Sep 6 2017 Trip spans 5 days
Major Airline
Major Airline
PDX
ORD
4h 00m
nonstop
ORD
PDX
4h 31m
nonstop
Depart: Wed May 31 2017 Return: Sun Jun 4 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
PDX
ORD
4h 06m
nonstop
ORD
PDX
4h 23m
nonstop
Depart: Tue Nov 7 2017 Return: Sat Nov 11 2017 Trip spans 5 days
Major Airline
Major Airline
PDX
ORD
3h 50m
nonstop
ORD
PDX
4h 25m
nonstop
Depart: Sat Aug 26 2017 Return: Tue Sep 5 2017 Trip spans 11 days
Spirit Airlines
Spirit Airlines
PDX
ORD
4h 00m
nonstop
ORD
PDX
4h 31m
nonstop
Depart: Tue May 30 2017 Return: Sat Jun 3 2017 Trip spans 5 days
Delta
Delta
PDX
MDW
10h 34m
1 stop
MDW
PDX
7h 43m
1 stop
Depart: Wed Aug 30 2017 Return: Mon Sep 4 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
PDX
ORD
4h 00m
nonstop
ORD
PDX
4h 31m
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 Jun 2 - Aug 21
86 8:00 am 2:00 pm Jun 3 - Aug 19
319 2:35 pm 8:36 pm Jun 6 - Aug 16
319 2:35 pm 8:36 pm Jun 2 - Aug 21
2608 11:45 pm 5:35 am Jun 2 - Jun 5
2608 11:45 pm 5:35 am Jun 6 - Jun 16
2608 11:45 pm 5:35 am Jun 10 - Jun 10
2608 11:45 pm 5:35 am Jun 17 - Jul 1
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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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.

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^ The fares displayed in KAYAK ads found on other sites include all taxes and fees for economy class travel and were found by KAYAK users in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.
Airports
Origin

Portland
$169
Destination

Chicago
only $169
only $313
Airlines Airline reviews

238 travelers who booked a flight from Portland to Chicago rated their chosen airlines with an average of 5.9.

Overall
6.1
Boarding
6.6
Crew
6.7
Comfort
5.5
Food
4.8
Entertainment
4.6