Popular airlines from Chicago to Willamette Valley
Alaska Airlines
Delta
Southwest Airlines
Spirit Airlines
United
American Airlines
Frontier Airlines
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Today's featured flight deals from Chicago to Willamette Valley
Nonstop
Carry-on included
Lower price than typical
- Chicago (MDW) to Portland (PDX).Southwest Airlines, nonstop.Departing on Fri, Aug 29 at 8:50pm from Chicago, arriving at 11:05pm in Portland.Returning on Tue, Sep 2 at 12:30pm from Portland, arriving at 11:05pm in Chicago.Select Southwest Airlines flight departing on Fri, Aug 29 at 8:50pm from Chicago, returning on Tue, Sep 2 at 12:30pm from Portland priced at $21750% less than typical$217
- Chicago (ORD) to Portland (PDX).Alaska Airlines, nonstop.Departing on Wed, Aug 13 at 7:00am from Chicago, arriving at 9:25am in Portland.Returning on Mon, Aug 18 at 5:35pm from Portland, arriving at 11:39pm in Chicago.Select Alaska Airlines flight departing on Wed, Aug 13 at 7:00am from Chicago, returning on Mon, Aug 18 at 5:35pm from Portland priced at $20745% less than typical$207
- Chicago (MDW) to Portland (PDX).Southwest Airlines, nonstop.Departing on Tue, Aug 26 at 8:30pm from Chicago, arriving at 10:45pm in Portland.Returning on Sun, Aug 31 at 7:00am from Portland, arriving at 1:07pm in Chicago.Select Southwest Airlines flight departing on Tue, Aug 26 at 8:30pm from Chicago, returning on Sun, Aug 31 at 7:00am from Portland priced at $18945% less than typical$189
- Chicago (ORD) to Portland (PDX).American Airlines, nonstop.Departing on Fri, Aug 29 at 8:49pm from Chicago, arriving at 11:26pm in Portland.Returning on Tue, Sep 2 at 12:30pm from Portland, arriving at 11:05pm in Chicago.Select American Airlines flight departing on Fri, Aug 29 at 8:49pm from Chicago, returning on Tue, Sep 2 at 12:30pm from Portland priced at $21840% less than typical$218
- Chicago (ORD) to Portland (PDX).Alaska Airlines, nonstop.Departing on Fri, Aug 15 at 7:00am from Chicago, arriving at 9:25am in Portland.Returning on Mon, Aug 18 at 5:35pm from Portland, arriving at 11:39pm in Chicago.Select Alaska Airlines flight departing on Fri, Aug 15 at 7:00am from Chicago, returning on Mon, Aug 18 at 5:35pm from Portland priced at $21740% less than typical$217
- Chicago (ORD) to Portland (PDX).American Airlines, nonstop.Departing on Fri, Aug 22 at 8:49pm from Chicago, arriving at 11:26pm in Portland.Returning on Sun, Aug 31 at 7:00am from Portland, arriving at 1:07pm in Chicago.Select American Airlines flight departing on Fri, Aug 22 at 8:49pm from Chicago, returning on Sun, Aug 31 at 7:00am from Portland priced at $19845% less than typical$198
- Chicago (ORD) to Portland (PDX).Alaska Airlines, nonstop.Departing on Wed, Aug 27 at 2:07pm from Chicago, arriving at 4:36pm in Portland.Returning on Sun, Aug 31 at 11:00pm from Portland, arriving on Mon, Sep 1 at 5:00am in Chicago.Select Alaska Airlines flight departing on Wed, Aug 27 at 2:07pm from Chicago, returning on Sun, Aug 31 at 11:00pm from Portland priced at $18845% less than typical$188
- Chicago (MDW) to Portland (PDX).Southwest Airlines, nonstop.Departing on Thu, Aug 21 at 8:50pm from Chicago, arriving at 11:05pm in Portland.Returning on Tue, Aug 26 at 9:20am from Portland, arriving at 3:15pm in Chicago.Select Southwest Airlines flight departing on Thu, Aug 21 at 8:50pm from Chicago, returning on Tue, Aug 26 at 9:20am from Portland priced at $22735% less than typical$227
- Chicago (ORD) to Portland (PDX).Alaska Airlines, nonstop.Departing on Thu, Aug 14 at 7:00am from Chicago, arriving at 9:25am in Portland.Returning on Tue, Aug 19 at 5:35pm from Portland, arriving at 11:39pm in Chicago.Select Alaska Airlines flight departing on Thu, Aug 14 at 7:00am from Chicago, returning on Tue, Aug 19 at 5:35pm from Portland priced at $20735% less than typical$207
Cheap Flights from Chicago to Willamette Valley (CHI-RDM)
Prices were available within the past 7 days and start at $81 for one-way flights and $173 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sat, Aug 9 - Mon, Aug 11
ORD
Chicago
PDX
Portland
$173 Roundtrip, just found
$173
Roundtrip
just found
Wed, Aug 27 - Sun, Aug 31
ORD
Chicago
PDX
Portland
$187 Roundtrip, just found
$187
Roundtrip
just found
Tue, Aug 19 - Tue, Aug 26
MDW
Chicago
PDX
Portland
$197 Roundtrip, just found
$197
Roundtrip
just found
Wed, Oct 22 - Wed, Oct 29
RFD
Rockford
PDX
Portland
$227 Roundtrip, found 1 day ago
$227
Roundtrip
found 1 day ago
Tue, Aug 26 - Tue, Aug 26
ORD
Chicago
MFR
Medford
$250 Roundtrip, found 1 day ago
$250
Roundtrip
found 1 day ago
Sat, Oct 11 - Sat, Oct 11
ORD
Chicago
RDM
Redmond
$253 Roundtrip, just found
$253
Roundtrip
just found
Find the cheapest month to fly from Chicago (CHI) to Portland (PDX)
August is typically the cheapest month to fly
From $98 - $220 per traveler.
Graph displaying average flight prices per month
Alternative airports
Prices were available within the past 7 days. Prices and availability are subject to change.
Select flight to Portland Intl. PDX. Cheapest option available. Flights from $240
PDX
Portland Intl.
Cheapest
Select flight to Mahlon Sweet Field EUG. Flights from $527
EUG
Mahlon Sweet Field
Select flight to Rogue Valley Intl. MFR. Flights from $514
MFR
Rogue Valley Intl.
Select flight to Robert's Field RDM. Flights from $421
RDM
Robert's Field
Select flight to Southwest Oregon Regional OTH. Flights from $534
OTH
Southwest Oregon Regional
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