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$105+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PWM
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
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Cheap 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 April 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$254
(Delta)

One-way from

$105
(Southwest)

Popular in

July

Cheapest in

September

Average price

$479

Good round-trip deal

$400 or less
Provider with most accurate pricing for Chicago Midway-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Portland flights.
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From Chicago Midway to Portland
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One-way flight from Chicago Midway to Portland
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Chicago Midway to Portland.
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Find 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 April 29, 2025.

This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 5/244:15 pmMDW - PWM
1 stop6h 44mDelta
Sun 5/256:05 amPWM - MDW
2 stops7h 23mDelta
Deal found 4/29$254
This Southwest deal was found by Cheapflights users on 4/29. 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.
Thu 8/215:40 amMDW - PWM
1 stop6h 35mSouthwest
Sun 8/245:35 amPWM - MDW
2 stops11h 00mSouthwest
Deal found 4/29$260

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 April 29, 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

Sat 5/24

4:15 pm-11:59 pm

1 stop6h 44m

Portland

Sun 5/25

6:05 am-12:28 pm

2 stops7h 23m

$254

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 8/21

5:40 am-1:15 pm

1 stop6h 35m

Portland

Sun 8/24

5:35 am-3:35 pm

2 stops11h 00m

$260

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 8/26

11:40 am-2:55 pm

Nonstop2h 15m

$105

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 7/1

4:26 pm-12:26 am

1 stop7h 00m

$109

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sun 5/18

10:55 am-7:33 pm

1 stop7h 38m

$128

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 5/29

8:20 pm-9:43 am

3 stops36h 23m

$494

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Portland, Maine flight deals on Cheapflights vs. FlightHub >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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland, Maine (average of $296). Flying from Chicago Midway Airport to Portland, Maine in May is currently the most expensive (average of $405). 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 April 29, 2025.

It’s typically best to fly out from Chicago Midway Airport to Portland, Maine at noon. Doing so could potentially save you 18% on the flight price compared to flying in the afternoon, which is usually more expensive.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, Maine, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 29, 2025.
Read reviews from past customers who have flown Southwest, Delta and Frontier from Chicago to Portland. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,936 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

  • What are the cheapest airlines flying from Chicago Midway Airport to Portland, Maine round-trip?

    Flying on Delta is currently your cheapest option to Portland, Maine, with prices starting at $254. Another option worth looking into is Southwest, starting at $260 round trip. You may be able to fly from Chicago Midway Airport to Portland, Maine for 35% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Portland, Maine one-way?

    The cheapest airlines for a one-way flight from Chicago Midway Airport to Portland, Maine are Southwest ($105), Delta ($109), and Frontier ($128).

  • What are the cheapest flights from Chicago Midway Airport to Portland, Maine?

    Looking for the cheapest flight from Chicago Midway Airport to Portland, Maine? While on average our users pay $435, our data indicates the cheapest price to be $279. The most popular route (Chicago Midway - Portland), is priced around $223.

  • 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland, Maine (average of $296). Flying from Chicago Midway Airport to Portland, Maine in May is currently the most expensive (average of $405). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
North Conway
Bath
Brunswick
Auburn
Conway
Lewiston

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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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$191Average$406FlexibilityNo cancel feeOn-time63%

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