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: Thu Dec 14 2017 Return: Wed Dec 20 2017 Trip spans 7 days
American Airlines
American Airlines
PWM
ORD
7h 22m
1 stop
ORD
PWM
5h 51m
1 stop
Depart: Thu Feb 15 2018 Return: Sat Feb 17 2018 Trip spans 3 days
United
United
PWM
ORD
6h 52m
1 stop
ORD
PWM
23h 17m
1 stop
Depart: Wed Jan 3 2018 Return: Fri Jan 12 2018 Trip spans 10 days
Delta
Delta
PWM
MDW
20h 51m
2 stops
MDW
PWM
7h 41m
2 stops
Depart: Fri Dec 15 2017 Return: Sun Dec 17 2017 Trip spans 3 days
American Airlines
American Airlines
PWM
ORD
6h 00m
1 stop
ORD
PWM
5h 51m
1 stop
Depart: Sun Dec 17 2017 Return: Mon Dec 25 2017 Trip spans 9 days
American Airlines
American Airlines
PWM
ORD
6h 04m
1 stop
ORD
PWM
5h 51m
1 stop
Depart: Thu Jan 4 2018 Return: Fri Jan 12 2018 Trip spans 9 days
American Airlines
American Airlines
PWM
ORD
6h 04m
1 stop
ORD
PWM
4h 40m
1 stop
Depart: Thu Feb 22 2018 Return: Sat Feb 24 2018 Trip spans 3 days
United
United
PWM
ORD
5h 29m
1 stop
ORD
PWM
17h 53m
1 stop
Depart: Fri Jan 19 2018 Return: Thu Jan 25 2018 Trip spans 7 days
American Airlines
American Airlines
PWM
ORD
6h 03m
1 stop
ORD
PWM
7h 08m
1 stop
Depart: Sun Jan 28 2018 Return: Tue Jan 30 2018 Trip spans 3 days
Delta
Delta
PWM
MDW
7h 19m
2 stops
MDW
PWM
9h 13m
2 stops
Depart: Sun Jan 28 2018 Return: Tue Jan 30 2018 Trip spans 3 days
American Airlines
American Airlines
PWM
ORD
6h 18m
1 stop
ORD
PWM
5h 52m
1 stop
Depart: Wed Dec 13 2017 Return: Tue Dec 19 2017 Trip spans 7 days
Delta
Delta
PWM
MDW
16h 01m
2 stops
MDW
PWM
11h 01m
2 stops
Depart: Thu Feb 8 2018 Return: Sat Feb 10 2018 Trip spans 3 days
American Airlines
American Airlines
PWM
ORD
7h 47m
1 stop
ORD
PWM
7h 08m
1 stop
Depart: Thu Dec 21 2017 Return: Tue Dec 26 2017 Trip spans 6 days
United
United
PWM
ORD
3h 08m
nonstop
ORD
PWM
4h 12m
1 stop
Depart: Wed Jan 3 2018 Return: Sat Jan 6 2018 Trip spans 4 days
Delta
Delta
PWM
MDW
20h 51m
2 stops
MDW
PWM
27h 18m
2 stops
Depart: Mon Dec 18 2017 Return: Mon Dec 25 2017 Trip spans 8 days
American Airlines
American Airlines
PWM
ORD
5h 02m
1 stop
ORD
PWM
5h 51m
1 stop
Depart: Sat Dec 23 2017 Return: Mon Dec 25 2017 Trip spans 3 days
United
United
PWM
ORD
3h 08m
nonstop
ORD
PWM
5h 10m
1 stop
Depart: Fri Jan 19 2018 Return: Thu Jan 25 2018 Trip spans 7 days
Delta
Delta
PWM
MDW
7h 19m
2 stops
MDW
PWM
7h 41m
2 stops
Depart: Wed Dec 20 2017 Return: Mon Dec 25 2017 Trip spans 6 days
American Airlines
American Airlines
PWM
ORD
5h 50m
1 stop
ORD
PWM
7h 56m
1 stop
Depart: Sat Dec 23 2017 Return: Tue Dec 26 2017 Trip spans 4 days
United
United
PWM
ORD
3h 08m
nonstop
ORD
PWM
4h 12m
1 stop
Depart: Sun Dec 31 2017 Return: Mon Jan 8 2018 Trip spans 9 days
American Airlines
American Airlines
PWM
ORD
5h 50m
1 stop
ORD
PWM
4h 40m
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
3405 5:45 am 7:50 am Dec 1 - Dec 19
4008 6:05 am 8:13 am Dec 20 - Dec 30
4008 6:05 am 8:13 am Jan 1 - Jan 7
3911 10:55 am 1:03 pm Dec 21 - Jan 7
3911 11:12 am 1:20 pm Dec 20 - Dec 20
4219 4:20 pm 6:24 pm Dec 20 - Dec 29
4219 4:20 pm 6:24 pm Dec 25 - Dec 25
4219 4:20 pm 6:24 pm Dec 23 - Dec 23
4219 4:20 pm 6:24 pm Jan 1 - Jan 7
4219 4:20 pm 6:24 pm Dec 24 - Dec 31
3572 4:35 pm 6:35 pm Nov 30 - Dec 19
4219 4:35 pm 6:35 pm Nov 29 - Dec 13
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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Airports
Origin

Portland
$259
Destination

Chicago
only $259
only $348