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Cheap Flights From Portland, Oregon (PDX) To Chicago, Illinois (MDW)

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Fares from Portland, OR (PDX)
$298 RT to
Chicago, IL (MDW)
$298 RT Portland to Chicago, IL
Airline(s)
Southwest
Seats:
Seats are not available on all flights or all dates of travel. You may need to have flexible travel dates to find this fare. Fares for travel on holidays may be higher.
Adv. Purchase:
14 Days
Available:
7 days/week, if available
Travel Ending:
Tuesday, 20 May 2014
More Details:
Non-Stop Flights, No min. stay, Fare can be bought one-way for half the lowest roundtrip price
Last Updated:
Wednesday, 16 April 2014
Our Notes:
This is a fare from Southwest. Visit Southwest.com to find this fare. Other airlines often match Southwest sales, so search other sites to find your best option.
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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.

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"Great hotel" 04/16/2014
"Weekend Getaway" 04/15/2014
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"Not as Advertised" 04/15/2014
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"Excellent service, great value" 03/07/2014

More Flights From Portland To Chicago (PDX-MDW)

Price
Details
$322 RT Year-round travel (Delta) See all details »
  • Airline(s):
    Delta
  • Seats are:
    Seats Are Not Available On All Flights Or All Dates Of Travel. You May Need To Have Flexible Travel Dates To Find This Fare. Fares For Travel On Holidays May Be Higher.
  • Advance Purchase:
    7 Days
  • Available for travel:
    7 Days/week, If Available
  • More Details:
    Year-round Travel
  • Last Updated:
    Wednesday, April 16, 2014
  • Our Notes:
    Summer Travel Is Scarce At This Price.

Reviews for Portland to Chicago (PDX-MDW)

based on 2 reviews
Flown this route before? Write a review
    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Always do it right.

    by marlynrlewis on April 14, 2011

    Flight from Portland to Chicago

    Airline:
    Southwest
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    April 2011
    Seat Class:
    economy

    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.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Reliable Travel for the $$$

    by tbenton on April 21, 2010

    Flight from Portland to Chicago

    Airline:
    Southwest
    Number of Stops:
    1 stop in Denver, Colorado
    Date of Flight:
    April 2010
    Seat Class:
    economy

    Another Southwest flight meets or exceeds all the others. I had no complaints with anything. We even had a non-stop return flight that got in 15 minutes early.

    The legroom is exceptional for Economy class. I am 6' and had no knees crunched.

Flown this route before? Write a review
Sample Fares found by other travelers within the past 72 hours
Price From/To Depart/Return Airline
$398 Flight from Portland to Midway (PDX-MDW) Tue, May 6 - Thu, May 8 Delta Air Lines
$413 Flight from Portland to Midway (PDX-MDW) Thu, May 8 - Fri, May 16 Delta Air Lines
$440 Flight from Portland to Midway (PDX-MDW) Wed, Aug 6 - Wed, Aug 20 Delta Air Lines
$443 Flight from Portland to Midway (PDX-MDW) Thu, May 8 - Fri, May 16 Delta Air Lines
$464 Flight from Portland to Midway (PDX-MDW) Wed, Jun 4 - Wed, Jun 11 Delta Air Lines
$470 Flight from Portland to Midway (PDX-MDW) Wed, Aug 6 - Wed, Aug 20 Delta Air Lines
$497 Flight from Portland to Midway (PDX-MDW) Wed, Aug 6 - Thu, Aug 21 Delta Air Lines
$553 Flight from Portland to Midway (PDX-MDW) Wed, Aug 6 - Mon, Aug 11 Delta Air Lines
$586 Flight from Portland to Midway (PDX-MDW) Sun, Jun 29 - Tue, Jul 1 Alaska Airlines
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 sometimes offer nonstop cheap flights from Portland to Chicago:

Transwest Air

As an alternative to flying from Portland, you may also want to try searching for cheap flights from Eugene (EUG).
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