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Get United's best fares today on flights from Portland to Chicago from *

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Low fare calendar for flights from Portland (PWM) to Chicago (ORD)

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Lowest PriceToday
*Prices have been available for round trips within the last 48 hours and may not be currently available. Fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.

Looking for additional flights from Portland to Chicago?

FromToDatesFare TypePrice

Portland (PWM)

Chicago (ORD)

Depart: 03/10/20

Return: 03/17/20

Roundtrip
from
$226*
Viewed:6hoursago

Portland (PWM)

Chicago (ORD)

Depart: 02/04/20

Return: 02/18/20

Roundtrip
from
$217*
Viewed:1dayago

Portland (PWM)

Chicago (ORD)

Depart: 02/04/20

Return: 02/11/20

Roundtrip
from
$217*
Viewed:1dayago

Portland (PWM)

Chicago (ORD)

Depart: 02/05/20

Return: 02/12/20

Roundtrip
from
$217*
Viewed:1dayago

Portland (PWM)

Chicago (ORD)

Depart: 03/04/20

Return: 03/11/20

Roundtrip
from
$226*
Viewed:1dayago

Portland (PWM)

Chicago (ORD)

Depart: 03/10/20

Return: 03/24/20

Roundtrip
from
$226*
Viewed:1dayago

Portland (PWM)

Chicago (ORD)

Depart: 04/08/20

Return: 04/15/20

Roundtrip
from
$226*
Viewed:1dayago

Portland (PWM)

Chicago (ORD)

Depart: 04/07/20

Return: 04/14/20

Roundtrip
from
$226*
Viewed:1dayago

Portland (PWM)

Chicago (ORD)

Depart: 03/17/20

Return: 03/24/20

Roundtrip
from
$226*
Viewed:1dayago

Portland (PWM)

Chicago (ORD)

Depart: 02/25/20

Return: 03/03/20

Roundtrip
from
$226*
Viewed:1dayago

*Prices have been available for round trips within the last 48 hours and may not be currently available. Fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.

Weather in Chicago

Tuesday broken clouds
31°F 01/28/20
Wednesday light snow
31°F 01/29/20
Thursday few clouds
30°F 01/30/20
Friday light snow
31°F 01/31/20
Saturday light snow
33°F 02/01/20
Sunday sky is clear
39°F 02/02/20
Monday moderate rain
36°F 02/03/20
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