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$115+ Cheap flights from Midway (MDW) to Portland, ME (PWM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PWM
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Midway to Portland

Cheapest flights from Midway to Portland
Explore the most affordable flight options available from Midway to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This Southwest deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/235:25 pmMDW - PWM
2 stops5h 40mSouthwest
Sat 1/35:15 amPWM - MDW
1 stop4h 40mSouthwest
Deal found 12/10$329
This Southwest deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/125:10 amMDW - PWM
1 stop5h 00mSouthwest
Sat 1/175:10 amPWM - MDW
1 stop7h 15mSouthwest
Deal found 12/11$339
This Delta deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1710:49 amMDW - PWM
2 stops11h 32mDelta
Tue 1/66:00 amPWM - MDW
2 stops13h 32mDelta
Deal found 12/10$374
This Southwest deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:40 amMDW - PWM
1 stop4h 30mSouthwest
Wed 12/173:30 pmPWM - MDW
1 stop6h 35mSouthwest
Deal found 12/10$434
This Delta deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/109:34 amMDW - PWM
1 stop5h 33mDelta
Sun 12/146:08 amPWM - MDW
1 stop6h 47mDelta
Deal found 12/10$449
This Delta deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:29 pmMDW - PWM
1 stop6h 14mDelta
Tue 1/612:48 pmPWM - MDW
2 stops10h 19mDelta
Deal found 12/10$456

Find flight deals from Midway to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Portland (PWM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$229
(Southwest)

One-way from

$115
(Delta)

Popular in

April

Cheapest in

September

Average price

$264
Provider with most accurate pricing for Chicago Midway-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Portland flights.
Search Deals
From Chicago Midway to Portland
Search Deals
One-way flight from Chicago Midway to Portland
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Portland that are best for you.

Fly from

Midway

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 1/13

6:50 am-12:10 pm

1 stop4h 20m

Portland

Wed 1/14

5:45 am-1:55 pm

2 stops9h 10m

$234

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sat 1/10

9:32 am-10:27 pm

2 stops11h 55m

Portland

Sat 1/17

6:00 am-12:48 pm

2 stops7h 48m

$239

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 1/23

12:48 pm-11:22 pm

2 stops9h 34m

Portland

Mon 1/26

2:35 pm-10:22 pm

2 stops8h 47m

$239

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 1/13

1:28 pm-11:22 pm

2 stops8h 54m

Portland

Wed 1/14

12:20 pm-5:34 pm

1 stop6h 14m

$279

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 3/23

9:32 am-4:10 pm

1 stop5h 38m

Portland

Thu 3/26

12:50 pm-5:55 pm

1 stop6h 05m

$299

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 3/23

4:05 pm-12:05 am

2 stops7h 00m

Portland

Thu 3/26

5:30 pm-11:35 pm

1 stop7h 05m

$325

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 12/23

5:25 pm-12:05 am

2 stops5h 40m

Portland

Sat 1/3

5:15 am-8:55 am

1 stop4h 40m

$329

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 3/20

6:35 am-11:55 am

1 stop4h 20m

Portland

Mon 3/23

5:30 pm-11:35 pm

1 stop7h 05m

$348

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sun 1/4

12:45 pm-12:20 am

2 stops10h 35m

Portland

Sat 1/10

6:00 am-4:16 pm

2 stops11h 16m

$349

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sat 3/28

9:32 am-4:10 pm

1 stop5h 38m

Portland

Fri 4/3

12:50 pm-5:55 pm

1 stop6h 05m

$369

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 18 results
1
2

Compare providers for flights from Midway to Portland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Portland in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Portland, Maine flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Portland, Maine flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Portland, Maine flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Portland, Maine flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Portland, Maine flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Portland

What is the cheapest month to book a flight from Chicago Midway Airport to Portland, Maine?

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland, Maine (average of $92). Flying from Chicago Midway Airport to Portland, Maine in April is currently the most expensive (average of $188). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to PWM?

Find hourly flight availability from Midway to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.

It’s typically best to fly out from Chicago Midway Airport to Portland, Maine in the afternoon. Doing so could potentially save you 55% on the flight price compared to flying in the evening, which is usually more expensive.

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated December 12, 2025.
Get a feel of what it's like to fly with Southwest from Chicago Midway Airport to Portland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,253 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midway to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Portland from Chicago Midway?

    For a flight from Chicago Midway to Portland, you will be flying into Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 0 inbound flights from Chicago Midway per day. 1 airline has flights to Portland from Chicago Midway on a regular basis.

  • How long is the flight from Chicago Midway Airport to Portland, Maine?

    Airlines like Southwest and Delta fly from Chicago Midway Airport to Portland, Maine in about 4h 20m. The time it takes to get you to your destination can typically vary by up to 7h 35m. The distance between Chicago Midway Airport and Portland, Maine is about 892 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What is the cheapest airline to fly from Chicago Midway Airport to Portland, Maine round-trip?

    Flying on Southwest is currently your cheapest option to Portland, Maine, with prices starting at $313.

  • Can I find deals for flights from Midway to Portland that include hotel bookings?

    Yes. In addition to deals on Midway to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Portland.

  • Can I find deals for business class flights from Midway to Portland?

    Yes. Cheapflights offers flight deals from Midway to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Portland, Maine?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland, Maine (average of $92). Flying from Chicago Midway Airport to Portland, Maine in April is currently the most expensive (average of $188). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Brunswick
Auburn
Conway

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Top airline flying from Midway to Portland

Discover the top airline that operate flights from Midway to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$313Average$411FlexibilityNo cancel feeOn-time63%

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