Get United's best fares today on flights from Portland, OR to Chicago from $281

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Search flights from Portland, OR to Chicago (PDX - ORD)

July

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Depart: 07/01/19

Return: 07/15/19
from$ 471*Viewed: 1 hour ago

Depart: 07/02/19

Return: 07/09/19
from$ 439*Viewed: 1 hour ago

Depart: 07/03/19

Return: 07/10/19
from$ 431*Viewed: 1 hour ago

August

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Depart: 08/01/19

Return: 08/15/19
from$ 365*Viewed: 1 hour ago

Depart: 08/02/19

Return: 08/16/19
from$ 351*Viewed: 1 hour ago

Depart: 08/03/19

Return: 08/17/19
from$ 303*Viewed: 1 hour ago

September

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Depart: 09/01/19

Return: 09/08/19
from$ 299*Viewed: 1 hour ago

Depart: 09/02/19

Return: 09/16/19
from$ 431*Viewed: 1 hour ago

Depart: 09/03/19

Return: 09/17/19
from$ 289*Viewed: 1 hour ago
*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.

Plan ahead for flights from Portland, OR to Chicago (PDX - ORD)

from
to
Type
Dates
Price*
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart: 08/21/19
Return: 09/04/19
from$ 281*Viewed: 1 hour ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart: 08/27/19
Return: 09/10/19
from$ 281*Viewed: 1 hour ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart: 08/28/19
Return: 09/11/19
from$ 281*Viewed: 1 hour ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart: 08/31/19
Return: 09/14/19
from$ 281*Viewed: 1 hour ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart: 09/10/19
Return: 09/24/19
from$ 281*Viewed: 1 hour ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart: 08/21/19
Return: 08/28/19
from$ 281*Viewed: 1 hour ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart: 08/28/19
Return: 09/04/19
from$ 281*Viewed: 1 hour ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart: 08/31/19
Return: 09/07/19
from$ 281*Viewed: 1 hour ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart: 09/10/19
Return: 09/17/19
from$ 281*Viewed: 1 hour ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart: 08/24/19
Return: 09/07/19
from$ 285*Viewed: 1 hour ago
*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

66 °FSunday06/16/19
68 °FMonday06/17/19
77 °FTuesday06/18/19
79 °FWednesday06/19/19
64 °FThursday06/20/19
79 °FFriday06/21/19
79 °FSaturday06/22/19
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