Find Cheap Flights from Portland to Chicago (PWM - 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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Book cheap flights from Portland to Chicago

(Round-trip)
Depart: Tue May 16 2017 Return: Sat May 20 2017 Trip spans 5 days
American Airlines
American Airlines
PWM
ORD
7h 37m
1 stop
ORD
PWM
5h 52m
1 stop
Depart: Mon May 22 2017 Return: Tue May 30 2017 Trip spans 9 days
Major Airline
Major Airline
PWM
ORD
6h 21m
nonstop
ORD
PWM
11h 46m
nonstop
Depart: Tue May 23 2017 Return: Tue May 30 2017 Trip spans 8 days
JetBlue
JetBlue
PWM
ORD
11h 39m
1 stop
ORD
PWM
26h 15m
1 stop
Depart: Wed May 24 2017 Return: Tue May 30 2017 Trip spans 7 days
Delta
Delta
PWM
MDW
6h 05m
1 stop
MDW
PWM
6h 55m
1 stop
Depart: Thu Sep 21 2017 Return: Sun Sep 24 2017 Trip spans 4 days
American Airlines
American Airlines
PWM
ORD
5h 49m
1 stop
ORD
PWM
7h 25m
1 stop
Depart: Tue Oct 10 2017 Return: Sat Oct 14 2017 Trip spans 5 days
American Airlines
American Airlines
PWM
ORD
5h 49m
1 stop
ORD
PWM
6h 56m
1 stop
Depart: Fri Jun 16 2017 Return: Sun Jun 18 2017 Trip spans 3 days
Major Airline
Major Airline
PWM
ORD
14h 24m
1 stop
ORD
PWM
14h 22m
1 stop
Depart: Wed May 24 2017 Return: Wed May 31 2017 Trip spans 8 days
American Airlines
American Airlines
PWM
ORD
5h 54m
1 stop
ORD
PWM
4h 07m
1 stop
Depart: Wed Jul 19 2017 Return: Tue Jul 25 2017 Trip spans 7 days
Delta
Delta
PWM
MDW
7h 00m
1 stop
MDW
PWM
6h 40m
1 stop
Depart: Tue Jul 25 2017 Return: Tue Aug 1 2017 Trip spans 8 days
Major Airline
Major Airline
PWM
ORD
8h 33m
nonstop
ORD
PWM
5h 11m
nonstop
Depart: Tue May 23 2017 Return: Tue May 30 2017 Trip spans 8 days
Delta
Delta
PWM
MDW
6h 05m
1 stop
MDW
PWM
5h 55m
1 stop
Depart: Fri Aug 25 2017 Return: Sun Aug 27 2017 Trip spans 3 days
American Airlines
American Airlines
PWM
ORD
7h 00m
1 stop
ORD
PWM
7h 25m
1 stop
Depart: Fri Jun 2 2017 Return: Mon Jun 5 2017 Trip spans 4 days
Delta
Delta
PWM
MDW
6h 05m
1 stop
MDW
PWM
6h 55m
1 stop
Depart: Sun Jun 11 2017 Return: Mon Jun 12 2017 Trip spans 2 days
Major Airline
Major Airline
PWM
ORD
20h 25m
nonstop
ORD
PWM
17h 16m
nonstop
Depart: Fri Sep 15 2017 Return: Mon Sep 18 2017 Trip spans 4 days
Delta
Delta
PWM
MDW
6h 08m
1 stop
MDW
PWM
8h 55m
1 stop
Depart: Fri Apr 28 2017 Return: Sat Apr 29 2017 Trip spans 2 days
Major Airline
Major Airline
PWM
ORD
2h 47m
nonstop
ORD
PWM
0h 47m
nonstop
Depart: Tue Jun 27 2017 Return: Sun Jul 2 2017 Trip spans 6 days
American Airlines
American Airlines
PWM
ORD
7h 27m
1 stop
ORD
PWM
5h 02m
1 stop
Depart: Fri Jun 16 2017 Return: Sun Jun 18 2017 Trip spans 3 days
Delta
Delta
PWM
MDW
5h 40m
1 stop
MDW
PWM
5h 04m
1 stop
Depart: Tue Aug 1 2017 Return: Wed Aug 9 2017 Trip spans 9 days
Delta
Delta
PWM
MDW
6h 03m
1 stop
MDW
PWM
8h 55m
1 stop
Depart: Fri Aug 11 2017 Return: Sun Aug 13 2017 Trip spans 3 days
American Airlines
American Airlines
PWM
ORD
7h 34m
1 stop
ORD
PWM
5h 32m
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
3632 6:20 am 8:15 am May 7 - May 21
4008 6:20 am 8:15 am Apr 30 - May 5
4671 6:20 am 8:15 am May 28 - Jun 3
4671 6:20 am 8:15 am May 6 - May 27
3809 11:30 am 1:24 pm Apr 23 - May 4
3809 11:30 am 1:20 pm May 6 - May 21
3809 11:30 am 1:20 pm Jun 1 - Jun 7
4705 11:30 am 1:20 pm May 5 - May 26
4705 11:30 am 1:20 pm May 27 - May 31
4219 4:40 pm 6:35 pm Apr 23 - May 4
3546 4:43 pm 6:35 pm May 28 - May 28
4219 4:43 pm 6:35 pm May 29 - Jun 7
4219 4:43 pm 6:35 pm May 5 - May 27
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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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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
$288
Destination

Chicago
only $288
only $410