Book United Portland, OR to Chicago flight deals from $237

Select journey type

Enter to select travel class and passengers

  1. Home
  2. United flights
  3. Flights to the United States
  4. Portland, OR - Chicago

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

November

Skip to content

Tuesday 6th

Return Tuesday 13th
from$ 237*Viewed: 2 hours ago

Wednesday 14th

Return Thursday 29th
from$ 237*Viewed: 3 hours ago

Wednesday 28th

Return Thursday 13th
from$ 237*Viewed: 3 hours ago

December

Skip to content

Saturday 1st

Return Sunday 16th
from$ 257*Viewed: 3 hours ago

Monday 24th

Return Tuesday 8th
from$ 264*Viewed: 3 hours ago

Monday 31st

Return Tuesday 15th
from$ 264*Viewed: 3 hours ago

January

Skip to content

Wednesday 9th

Return Thursday 24th
from$ 245*Viewed: 3 hours ago

Tuesday 15th

Return Wednesday 30th
from$ 237*Viewed: 3 hours ago

Wednesday 16th

Return Thursday 31st
from$ 237*Viewed: 3 hours 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..
Cruise ships and tour boats docked by a ferris wheel and urban buildings at Navy Pier in Chicago

Plan ahead for flights from Portland, OR to Chicago

from
to
Type
Dates
Price*
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart Wed 14 Nov 2018
Return Thu 29 Nov 2018
from$ 237*Viewed: 3 hours ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart Wed 28 Nov 2018
Return Thu 13 Dec 2018
from$ 237*Viewed: 3 hours ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart Tue 15 Jan 2019
Return Wed 30 Jan 2019
from$ 237*Viewed: 3 hours ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart Wed 16 Jan 2019
Return Thu 31 Jan 2019
from$ 237*Viewed: 3 hours ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart Tue 6 Nov 2018
Return Tue 13 Nov 2018
from$ 237*Viewed: 2 hours ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart Wed 7 Nov 2018
Return Wed 14 Nov 2018
from$ 237*Viewed: 2 hours ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart Tue 13 Nov 2018
Return Wed 28 Nov 2018
from$ 245*Viewed: 3 hours ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart Wed 9 Jan 2019
Return Thu 24 Jan 2019
from$ 245*Viewed: 3 hours ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart Mon 7 Jan 2019
Return Tue 22 Jan 2019
from$ 254*Viewed: 3 hours ago
Portland, OR (PDX)
to Chicago (ORD)
Roundtrip
Depart Tue 8 Jan 2019
Return Wed 23 Jan 2019
from$ 254*Viewed: 3 hours 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

39 °FSunday10/21/2018
53 °FMonday10/22/2018
49 °FTuesday10/23/2018
53 °FWednesday10/24/2018
53 °FThursday10/25/2018
53 °FFriday10/26/2018
58 °FSaturday10/27/2018
Powered by: OpenWeatherMap.org