Home >> Fares From A City >> Chicago, IL >> Chicago, IL (MDW) To Portland, ME (PWM)
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HOW TO FIND THIS FARE
  • AIRLINES
    Southwest
  • ADVANCE PURCHASE REQUIRED
    14 DAYS BEFORE TRAVEL
  • DAYS AVAILABLE FOR TRAVEL
    Mon-Thur & Sat
  • TRAVEL STARTING
    Tue, August 23, 2016
  • TRAVEL ENDING
    Wed, February 15, 2017
Giuliana M.
Staff Airfare Analyst
Giuliana's Notes:
No min. stay. Fare can be bought one-way for half the lowest roundtrip price. No peak holiday travel at this 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.


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.
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Found by other travelers: Chicago, IL (MDW) to Portland, ME (PWM)
$620
Flight from Chicago to Portland (MDW - PWM)
Fri, Aug 1 - Fri, Aug 8
Delta
$585
Flight from Chicago to Portland (MDW - PWM)
Thu, Aug 28 - Mon, Sep 1
Delta
$494
Flight from Chicago to Portland (MDW - PWM)
Wed, Aug 27 - Mon, Sep 1
Delta
$654
Flight from Chicago to Portland (MDW - PWM)
Wed, Jun 11 - Wed, Jun 25
Delta
$749
Flight from Chicago to Portland (MDW - PWM)
Sun, Jun 29 - Sat, Jul 5
Delta
$650
Flight from Chicago to Portland (MDW - PWM)
Sun, Jun 29 - Fri, Jul 4
Delta
$532
Flight from Chicago to Portland (MDW - PWM)
Thu, Aug 28 - Sun, Aug 31
Delta
$609
Flight from Chicago to Portland (MDW - PWM)
Fri, Aug 29 - Mon, Sep 1
Delta
$689
Flight from Chicago to Portland (MDW - PWM)
Fri, Jul 18 - Tue, Jul 22
Delta
$390
Flight from Chicago to Portland (MDW - PWM)
Wed, Sep 24 - Wed, Oct 1
Delta
There are approximately 5 flights covering the route from Midway Airport in Chicago to Portland International Jetport in Portland, provided by as many as 1 airlines.
The following airlines often offer cheap flights from Chicago to Portland
Delta
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