Home >> Fares From A City >> Portland, OR >> Portland, OR (PDX) To Chicago, IL (MDW)
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HOW TO FIND THIS FARE
  • AIRLINES
    Delta
  • TRAVEL STARTING
    Tue, September 15, 2015
Giuliana M.
Staff Airfare Analyst
Giuliana's Notes:
No peak summer travel at this price. No peak holiday travel at this price. 330 day travel period.

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.

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.

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
Close Details
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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