Find Deals on 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 Mar 14 2017 Return: Wed Mar 29 2017 Trip spans 16 days
JetBlue
JetBlue
PWM
ORD
5h 16m
1 stop
ORD
PWM
4h 39m
1 stop
Depart: Mon Mar 20 2017 Return: Mon Mar 27 2017 Trip spans 8 days
Major Airline
Major Airline
PWM
ORD
5h 16m
nonstop
ORD
PWM
26h 38m
nonstop
Depart: Fri Mar 10 2017 Return: Sat Mar 11 2017 Trip spans 2 days
Delta
Delta
PWM
MDW
4h 17m
1 stop
MDW
PWM
4h 38m
1 stop
Depart: Thu Mar 23 2017 Return: Mon Mar 27 2017 Trip spans 5 days
Delta
Delta
PWM
ORD
5h 50m
1 stop
ORD
PWM
4h 12m
1 stop
Depart: Sat Apr 8 2017 Return: Sat Apr 15 2017 Trip spans 8 days
Major Airline
Major Airline
PWM
ORD
22h 58m
nonstop
ORD
PWM
4h 39m
nonstop
Depart: Mon Mar 27 2017 Return: Sat Apr 1 2017 Trip spans 6 days
Delta
Delta
PWM
MDW
4h 17m
1 stop
MDW
PWM
4h 20m
1 stop
Depart: Thu May 4 2017 Return: Sun May 7 2017 Trip spans 4 days
Major Airline
Major Airline
PWM
ORD
23h 42m
nonstop
ORD
PWM
11h 55m
nonstop
Depart: Thu Mar 30 2017 Return: Mon Apr 3 2017 Trip spans 5 days
Delta
Delta
PWM
ORD
5h 50m
1 stop
ORD
PWM
4h 00m
1 stop
Depart: Thu Aug 24 2017 Return: Mon Aug 28 2017 Trip spans 5 days
Major Airline
Major Airline
PWM
ORD
12h 29m
1 stop
ORD
PWM
4h 18m
1 stop
Depart: Tue Jun 20 2017 Return: Tue Jun 27 2017 Trip spans 8 days
JetBlue
JetBlue
PWM
ORD
6h 20m
1 stop
ORD
PWM
5h 11m
1 stop
Depart: Thu Apr 6 2017 Return: Sat Apr 8 2017 Trip spans 3 days
Delta
Delta
PWM
MDW
4h 55m
1 stop
MDW
PWM
4h 20m
1 stop
Depart: Fri Apr 28 2017 Return: Mon May 1 2017 Trip spans 4 days
Delta
Delta
PWM
ORD
4h 31m
1 stop
ORD
PWM
4h 22m
1 stop
Depart: Sun Apr 30 2017 Return: Tue May 2 2017 Trip spans 3 days
Delta
Delta
PWM
ORD
5h 57m
1 stop
ORD
PWM
3h 53m
1 stop
Depart: Sat Jul 29 2017 Return: Mon Aug 7 2017 Trip spans 10 days
Major Airline
Major Airline
PWM
ORD
23h 18m
nonstop
ORD
PWM
26h 27m
nonstop
Depart: Mon May 1 2017 Return: Thu May 4 2017 Trip spans 4 days
Delta
Delta
PWM
MDW
6h 09m
1 stop
MDW
PWM
3h 53m
1 stop
Depart: Tue May 2 2017 Return: Thu May 4 2017 Trip spans 3 days
Delta
Delta
PWM
MDW
4h 30m
1 stop
MDW
PWM
5h 38m
1 stop
Depart: Sat May 27 2017 Return: Tue May 30 2017 Trip spans 4 days
Delta
Delta
PWM
ORD
6h 53m
1 stop
ORD
PWM
5h 53m
1 stop
Depart: Wed May 31 2017 Return: Fri Jun 2 2017 Trip spans 3 days
Delta
Delta
PWM
ORD
6h 10m
1 stop
ORD
PWM
5h 53m
1 stop
Depart: Sat Jun 3 2017 Return: Mon Jun 5 2017 Trip spans 3 days
Delta
Delta
PWM
ORD
6h 22m
1 stop
ORD
PWM
4h 22m
1 stop
Depart: Sat Jun 3 2017 Return: Tue Jun 6 2017 Trip spans 4 days
Delta
Delta
PWM
MDW
6h 40m
1 stop
MDW
PWM
3h 53m
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
3568 6:20 am 8:15 am Mar 12 - Apr 2
4008 6:20 am 8:15 am Mar 13 - Apr 8
4008 6:20 am 8:15 am Mar 9 - Mar 11
3809 11:30 am 1:24 pm Apr 4 - Apr 14
4219 4:28 pm 6:29 pm Mar 5 - Mar 8
4219 4:40 pm 6:35 pm Apr 4 - Apr 21
4219 4:42 pm 6:29 pm Mar 16 - Mar 16
4219 4:43 pm 6:35 pm Mar 22 - Mar 24
4219 4:43 pm 6:35 pm Mar 14 - Mar 17
4219 4:43 pm 6:35 pm Mar 9 - Mar 10
4219 4:43 pm 6:35 pm Mar 28 - Apr 3
4219 4:48 pm 6:40 pm Apr 2 - Apr 2
4380 4:48 pm 6:40 pm Mar 19 - Mar 19
4380 4:48 pm 6:44 pm Mar 26 - Mar 26
3809 4:52 pm 6:44 pm Mar 13 - Mar 13
4380 5:00 pm 6:52 pm Mar 12 - Mar 12
3809 5:03 pm 6:55 pm Mar 21 - Mar 21
3809 5:08 pm 7:00 pm Mar 20 - Mar 27
3809 5:18 pm 7:10 pm Mar 23 - Mar 23
* 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
$230
Destination

Chicago
only $230
only $260