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

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Fares from Portland, OR (PDX)
$290 RT to
Chicago, IL (ORD)
Sorry this deal is over or has been sold out! But here’s another great Airfarewatchdog verified fare for this route!
$290 RT Portland to Chicago, IL
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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.
Travel Starting:
Wednesday, 07 January 2015
Travel Ending:
Wednesday, 11 February 2015
More Details:
Winter travel, No min. stay
Last Updated:
Thursday, 27 November 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. Use caution when booking as flights from/to Chicago area's O'hare (ORD) and Midway (MDW) airports will be shown. Lower fares may be available from/to nearby Chicago area airports.
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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.

More Flights From Portland To Chicago (PDX-ORD)

Price
Details
$365 RT Non-Stop Flights. No peak holiday travel at this price (United) See all details »
  • Airline(s):
    United
  • 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:
    Non-Stop Flights, No Peak Holiday Travel At This Price
  • Last Updated:
    Thursday, November 27, 2014
  • Our Notes:
    CheapAir charges a $9.95 booking fee. Use caution when booking as flights from/to Chicago area's O'hare (ORD) and Midway (MDW) airports will be shown. ...moreLower fares may be available from/to nearby Chicago area airports.
$375 RT Non-Stop Flights. No min. stay. No peak holiday travel at this price. N... (American) See all details »
  • Airline(s):
    American
  • 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:
    Saturday, June 6, 2015
  • More Details:
    Non-Stop Flights, No Min. Stay, No Peak Holiday Travel At This Price, No Peak Spring Break Travel At This Price
  • Last Updated:
    Wednesday, November 26, 2014
  • Our Notes:
    Blackouts: December 19-20, 26-29, 2014; January 3-4, February 16, March 15-22, April 12-19, May 21-25, 2015. CheapAir Charges A $9.95 Booking Fee.

Reviews for Portland to Chicago (PDX-ORD)

based on 7 reviews
Flown this route before? Write a review
    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Non-Stop to Chicago is the best way to go.

    by Ninos on March 13, 2013

    Flight from Portland to Chicago

    Airline:
    Alaska
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    February 2013
    Seat Class:
    economy

    Alaska Air is an asset when flying out of Portland. The direct flight to Chicago bets any of the local competition.

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    4. Seat Comfort:

    US Airways Bad Memory

    by ronbeedyahoo on December 31, 2011

    Flight from Portland to Chicago

    Airline:
    US Airways
    RT/OW
    Round Trip
    Number of Stops:
    1 stop in Phoenix, Arizona
    Date of Flight:
    November 2011
    Seat Class:
    economy

    I had to sleep overnight in Phoenix airport because the attendant said there was no more carry on baggage space. I registered my complaint that night online, and received verification from US Airways and nothing else. Tip; if you're not worried about lost baggage, take that flight and have ship your bags on the next flight.

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    4. Seat Comfort:

    Great flight staff, rough weather conditions

    by dmeininger on December 30, 2010

    Flight from Portland to Chicago

    Airline:
    Alaska
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    November 2010
    Seat Class:
    economy

    The flight staff to and from Chicago were terrific and helpful. The flight there was 30 min early! On the way back we had an extremely long descent, I think, do to the weather and it was quite painful for my children's ears. Also we checked in online.

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    Alaska Flights Terrific

    by fkousley on October 21, 2010

    Flight from Portland to Chicago

    Airline:
    Alaska
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    October 2010
    Seat Class:
    economy

    Flying Alaska is always my first choice. Fewer hassles, efficient boarding, ontime departures and landings. Direct routes are a plus, especially PDX to ORD and PDX to Boston.

    1. Flight Rating

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    United is a Rip-off!!

    by janiga on August 27, 2010

    Flight from Portland to Chicago

    Airline:
    United
    RT/OW
    One Way
    Number of Stops:
    No stops
    Date of Flight:
    August 2010
    Seat Class:
    economy

    The person directing us at the airport, for United was rude in the way he spoke to us. Then he weighted my bag to be checked and said that it was over weight which carried a fee of $125! I told him I do=i not know I was taking my bag on a vacation. I wrote United an email when I got home, and their response was that I was lucky that I was not charged $200! I have paid $25 for an over weight bag before. I also told them that the fact that I was not a "frequent flyer member",this was why they were not going to resolve t5his problem.

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    alaska airlines portland to chicago via Seattle

    by vickiseller on July 6, 2010

    Flight from Portland to Chicago

    Airline:
    Alaska
    RT/OW
    Round Trip
    Number of Stops:
    1 stop in Seattle, Washington
    Date of Flight:
    June 2010
    Seat Class:
    economy

    Portland airport I love - best in the country! There is wonderful shopping. The atmosphere is calming. There is usually lovely live music somewhere.

    If you are taking a "puddle jumper" to Seattle you are allowed to whiz through the first class inspection line.

    1. Flight Rating

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    4. Seat Comfort:

    Alaska Air provides the best experience in the air

    by walterhpdx on April 19, 2010

    Flight from Portland to Chicago

    Airline:
    Alaska
    Number of Stops:
    No stops
    Date of Flight:
    April 2010
    Seat Class:
    first

    I've belonged to the Alaska Airlines MVP Gold program for the last few years, and enjoy flying them quite a bit. Not only do they have convenient flights, but they have some of the best flight crews out there. Professional, enjoyable, personable; it's what flying USED to be like.

    Boarding is always easy, and you're met with a smile. My seat always has my personal bottle of water waiting for me, and assistance is just a quick glance away. The seats are comfortable, and the in-flight entertainment via digEplayers are innovative and an excellent way to pass the time.

    The only things that I would cite Alaska on is that their meals in First Class (yes, they still do serve hot meals!) are always meat based. It's okay - I'm used to it, being a vegetarian, so I bring along my own food.

    I wish Alaska flew EVERYWHERE my travels take me!

Flown this route before? Write a review
Sample Fares found by other travelers within the past 72 hours
Price From/To Depart/Return Airline
$378 Flight from Portland to O'Hare (PDX-ORD) Tue, Jun 10 - Sat, Jun 14 Spirit Airlines
$414 Flight from Portland to O'Hare (PDX-ORD) Tue, Jun 10 - Sat, Jun 14 Spirit Airlines
$484 Flight from Portland to O'Hare (PDX-ORD) Tue, Jun 10 - Wed, Jun 18 Spirit Airlines
$518 Flight from Portland to O'Hare (PDX-ORD) Thu, Jun 5 - Fri, Jun 6 Spirit Airlines
$518 Flight from Portland to O'Hare (PDX-ORD) Fri, Jun 6 - Mon, Jun 9 Spirit Airlines
$518 Flight from Portland to O'Hare (PDX-ORD) Fri, Jun 6 - Sun, Jun 8 Spirit Airlines
$544 Flight from Portland to O'Hare (PDX-ORD) Sat, Jun 7 - Wed, Jun 11 Delta Air Lines
$544 Flight from Portland to O'Hare (PDX-ORD) Tue, Jun 10 - Wed, Jun 11 Delta Air Lines
$546 Flight from Portland to O'Hare (PDX-ORD) Mon, Jun 9 - Tue, Jun 10 Spirit Airlines
$546 Flight from Portland to O'Hare (PDX-ORD) Mon, Jun 9 - Wed, Jun 11 Spirit Airlines
There are approximately 377 flights covering the route from Portland International Airport in Portland to O'Hare International Airport in Chicago, provided by as many as 8 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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