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

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Fares from Portland, OR (PDX)
$289 RT to
Chicago, IL (MDW)
$289 RT Portland to Chicago, IL
Airline(s)
Frontier
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:
10 Days
Available:
Mon-Wed & Fri-Sat
Travel Starting:
Friday, 31 October 2014
More Details:
Lowest fare found for travel within the next 30 days.
Last Updated:
Wednesday, 22 October 2014
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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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More Flights From Portland To Chicago (PDX-MDW)

Price
Details
$301 RT Fall travel. No min. stay. No peak holiday travel at this price (Frontier) See all details »
  • Airline(s):
    Frontier
  • 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.
  • More Details:
    Fall Travel, No Min. Stay, No Peak Holiday Travel At This Price
  • Last Updated:
    Wednesday, October 22, 2014
  • Our Notes:
    Frontier Charges A $25 Fee Each Way For Carry-on Bags Larger Than 18 X 14 X 8 In. CheapAir Charges A $9.95 Booking Fee.
$362 RT No min. stay. Winter travel; Nonstop flights. No peak holiday travel at... (Southwest) See all details »
  • Airline(s):
    Southwest
  • 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.
  • Available for travel:
    Mon-Thur & Sat
  • Travel starting:
    Wednesday, 03 December 2014
  • Travel ending:
    Wednesday, February 11, 2015
  • More Details:
    No Min. Stay, Winter Travel; Nonstop Flights, No Peak Holiday Travel At This Price
  • Last Updated:
    Tuesday, October 21, 2014
  • Our Notes:
    Travel December 3 through December 16, 2014 and January 6 through February 11, 2015. This is a fare from Southwest - visit Southwest.com to find this fare. ...moreOther airlines often match Southwest sales, so search other sites to find the best option. Nonstop flights may be available for this route but at a higher price.
$372 RT Non-Stop Flights. No min. stay. Fare can be bought one-way for half the... (Southwest) See all details »
  • Airline(s):
    Southwest
  • 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:
    14 Days
  • Available for travel:
    Mon-Thur & Sat
  • Travel ending:
    Thursday, March 5, 2015
  • More Details:
    Non-Stop Flights, No Min. Stay, Fare Can Be Bought One-way For Half The Lowest Roundtrip Price, No Peak Holiday Travel At This Price
  • Last Updated:
    Wednesday, October 22, 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 the best ...moreoption.

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
$546 Flight from Portland to Midway (PDX-MDW) Fri, Jun 13 - Sun, Jun 15 Delta Air Lines
$546 Flight from Portland to Midway (PDX-MDW) Thu, Jun 12 - Sun, Jun 15 Delta Air Lines
$584 Flight from Portland to Midway (PDX-MDW) Wed, Jul 2 - Wed, Jul 16 Delta Air Lines
$586 Flight from Portland to Midway (PDX-MDW) Wed, Jun 11 - Sun, Jun 15 Delta Air Lines
$606 Flight from Portland to Midway (PDX-MDW) Thu, Jul 3 - Tue, Jul 8 Frontier Airlines
$638 Flight from Portland to Midway (PDX-MDW) Fri, Jun 20 - Tue, Jul 1 Alaska Airlines
$683 Flight from Portland to Midway (PDX-MDW) Mon, Jun 9 - Thu, Jun 12 Delta Air Lines
$789 Flight from Portland to Midway (PDX-MDW) Thu, Jun 26 - Mon, Jun 30 Delta Air Lines
$797 Flight from Portland to Midway (PDX-MDW) Sun, Jun 22 - Mon, Jun 23 Frontier Airlines
$828 Flight from Portland to Midway (PDX-MDW) Thu, Jun 26 - Sun, Jun 29 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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