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: Wed May 31 2017 Return: Wed Jun 7 2017 Trip spans 8 days
American Airlines
American Airlines
PWM
ORD
7h 37m
1 stop
ORD
PWM
7h 12m
1 stop
Depart: Mon Oct 9 2017 Return: Wed Oct 11 2017 Trip spans 3 days
Major Airline
Major Airline
PWM
ORD
15h 14m
nonstop
ORD
PWM
11h 14m
nonstop
Depart: Sat Jul 8 2017 Return: Tue Jul 11 2017 Trip spans 4 days
Delta
Delta
PWM
MDW
4h 35m
1 stop
MDW
PWM
4h 10m
1 stop
Depart: Wed Aug 30 2017 Return: Mon Sep 11 2017 Trip spans 13 days
American Airlines
American Airlines
PWM
ORD
5h 49m
1 stop
ORD
PWM
5h 16m
1 stop
Depart: Wed Sep 20 2017 Return: Sun Sep 24 2017 Trip spans 5 days
American Airlines
American Airlines
PWM
ORD
7h 56m
1 stop
ORD
PWM
7h 25m
1 stop
Depart: Fri Nov 10 2017 Return: Sun Nov 12 2017 Trip spans 3 days
American Airlines
American Airlines
PWM
ORD
6h 42m
1 stop
ORD
PWM
6h 25m
1 stop
Depart: Fri Jul 28 2017 Return: Mon Jul 31 2017 Trip spans 4 days
Major Airline
Major Airline
PWM
ORD
6h 21m
nonstop
ORD
PWM
5h 11m
nonstop
Depart: Fri Aug 25 2017 Return: Mon Aug 28 2017 Trip spans 4 days
Delta
Delta
PWM
MDW
4h 24m
1 stop
MDW
PWM
4h 07m
1 stop
Depart: Fri Aug 25 2017 Return: Mon Aug 28 2017 Trip spans 4 days
Delta
Delta
PWM
ORD
4h 43m
1 stop
ORD
PWM
4h 07m
1 stop
Depart: Fri Jul 28 2017 Return: Mon Jul 31 2017 Trip spans 4 days
Major Airline
Major Airline
PWM
ORD
26h 16m
nonstop
ORD
PWM
26h 30m
nonstop
Depart: Wed Jun 14 2017 Return: Mon Jun 19 2017 Trip spans 6 days
American Airlines
American Airlines
PWM
ORD
7h 27m
1 stop
ORD
PWM
7h 12m
1 stop
Depart: Thu Aug 31 2017 Return: Mon Sep 4 2017 Trip spans 5 days
Delta
Delta
PWM
MDW
4h 24m
1 stop
MDW
PWM
6h 07m
1 stop
Depart: Fri Aug 11 2017 Return: Sun Aug 13 2017 Trip spans 3 days
Major Airline
Major Airline
PWM
ORD
26h 18m
nonstop
ORD
PWM
8h 17m
nonstop
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: Fri Sep 29 2017 Return: Sun Oct 1 2017 Trip spans 3 days
Delta
Delta
PWM
MDW
4h 04m
1 stop
MDW
PWM
4h 07m
1 stop
Depart: Sat Oct 7 2017 Return: Mon Oct 9 2017 Trip spans 3 days
Delta
Delta
PWM
MDW
4h 36m
1 stop
MDW
PWM
3h 52m
1 stop
Depart: Fri Oct 6 2017 Return: Sun Oct 8 2017 Trip spans 3 days
American Airlines
American Airlines
PWM
ORD
7h 00m
1 stop
ORD
PWM
6h 25m
1 stop
Depart: Fri Oct 20 2017 Return: Sun Oct 22 2017 Trip spans 3 days
Delta
Delta
PWM
MDW
4h 24m
1 stop
MDW
PWM
3h 52m
1 stop
Depart: Thu Nov 2 2017 Return: Sun Nov 5 2017 Trip spans 4 days
Delta
Delta
PWM
MDW
4h 24m
1 stop
MDW
PWM
6h 22m
1 stop
Depart: Fri Nov 3 2017 Return: Sun Nov 5 2017 Trip spans 3 days
Delta
Delta
PWM
MDW
4h 24m
1 stop
MDW
PWM
4h 07m
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
3680 6:15 am 8:03 am Jun 11 - Jun 25
3818 6:15 am 8:03 am Jun 8 - Jun 8
4484 6:15 am 7:58 am Jun 9 - Jun 30
4008 6:20 am 8:15 am Jun 4 - Jun 4
4671 6:20 am 8:15 am Jun 5 - Jun 7
4671 6:20 am 8:15 am May 28 - Jun 3
4484 6:25 am 8:06 am Jul 1 - Jul 1
4492 9:58 am 11:38 am Jun 11 - Jun 25
4568 11:25 am 1:05 pm Jun 8 - Jul 1
3809 11:30 am 1:20 pm Jun 1 - Jun 7
4705 11:30 am 1:20 pm May 22 - May 31
5553 1:05 pm 2:50 pm Jul 1 - Sep 5
4219 4:35 pm 6:26 pm Jun 8 - Jun 30
4219 4:40 pm 6:35 pm Jul 1 - Aug 14
4219 4:43 pm 6:35 pm May 29 - Jun 7
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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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,
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Airports
Origin

Portland
$269
Destination

Chicago
only $269
only $372