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
    21 DAYS BEFORE TRAVEL
  • DAYS AVAILABLE FOR TRAVEL
    Mon-Sun
  • TRAVEL ENDING
    Mon, April 24, 2017
Giuliana M.
Staff Airfare Analyst
Giuliana's Notes:
Certain travel dates only! 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.


To the best of our knowledge, there is a reasonable amount of seat availability at the stated price. Flexible travel dates may be required to find this rate; seats may not be available on all flights or all dates of travel. Holiday periods may be excluded. We monitor the availability of the fare and take efforts to remove and/or modify fares when no longer available.
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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