Home Fares From A City Portland, OR Portland, OR (PDX) To Chicago, IL (MDW)
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HOW TO FIND THIS FARE
  • AIRLINES
    Southwest
  • ADVANCE PURCHASE REQUIRED
    14 DAYS BEFORE TRAVEL
  • DAYS AVAILABLE FOR TRAVEL
    Mon-Sun
  • TRAVEL ENDING
    Wed, February 15, 2017
Giuliana M.
Staff Airfare Analyst
Giuliana's Notes:
Non-stop.
No min. stay. Fare can be bought one-way for half the lowest roundtrip price.
This is a fare from Southwest, please visit Southwest.com to find this fare. Other airlines often match Southwest sales, so search other sites to find the best option.
To the best of our knowledge, there is a reasonable amount of seat availability at the stated price. Flexible travel dates may be required to find this rate; seats may not be available on all flights or all dates of travel. Holiday periods may be excluded. We monitor the availability of the fare and take efforts to remove and/or modify fares when no longer available.
All mandatory taxes/fees are included in the price. Tax-inclusive fare may be a few dollars higher or lower depending on the airport you connect through, if any. Baggage fees, if applicable, and other optional fees are not included. Our Dealhounds found this airfare using flexible date search. This means we searched a range of dates to find you the best price.
More Details
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Reviews for Portland to Chicago
2 Traveler Reviews
"Always do it right."
Flight from Portland to Chicago
Airline: Southwest
RT/OW: roundtrip
Date of Flight: April 2011
Seat Class: economy
Check-in Experience
In-flight Service
Seat Comfort
On time, fast luggage arrival at destination, courteous flight attendants, better pricing than the competition as always. Ticket counter and gate people were very nice, too. I always recommend Southwest to anyone who flies.
Found by other travelers: Portland, OR (PDX) to Chicago, IL (MDW)
$522
Flight from Portland to Chicago (PDX - MDW)
Thu, Aug 7 - Fri, Aug 15
Frontier
$318
Flight from Portland to Chicago (PDX - MDW)
Thu, Sep 11 - Tue, Sep 16
Frontier
$574
Flight from Portland to Chicago (PDX - MDW)
Sun, Jul 27 - Thu, Jul 31
Frontier
$377
Flight from Portland to Chicago (PDX - MDW)
Wed, Oct 29 - Sun, Nov 2
Delta
$377
Flight from Portland to Chicago (PDX - MDW)
Thu, Oct 16 - Tue, Oct 21
Delta
$576
Flight from Portland to Chicago (PDX - MDW)
Mon, Jul 28 - Thu, Jul 31
Alaska
$606
Flight from Portland to Chicago (PDX - MDW)
Thu, Jul 24 - Sun, Jul 27
Frontier
$320
Flight from Portland to Chicago (PDX - MDW)
Thu, Sep 4 - Tue, Sep 9
Delta
$377
Flight from Portland to Chicago (PDX - MDW)
Fri, Sep 5 - Tue, Sep 9
Delta
$584
Flight from Portland to Chicago (PDX - MDW)
Wed, Jul 2 - Wed, Jul 16
Delta
There are approximately 24 flights covering the route from Portland International Airport in Portland to Midway Airport in Chicago, provided by as many as 7 airlines.
The following airlines often offer cheap flights from Portland to Chicago
Alaska
Continental
Southwest
United
Frontier
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