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$66+ Cheap flights from Portland, ME (PWM) to Midway (MDW)

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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
Feb 15 — Feb 221
Sat 2/15
Sat 2/22
1 adult, Economy
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Cheap flight deals from Portland to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Midway (MDW). 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 February 10, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$258
(Southwest)

One-way from

$66
(Mytrip)

Popular in

April

Cheapest in

September

Average price

$334

Good round-trip deal

$401 or less
Provider with most accurate pricing for Portland-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Portland-Chicago Midway flights.
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From Portland to Chicago Midway
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One-way flight from Portland to Chicago Midway
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Highest demand for flights based on searches. 16% potential increase in price ($75 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Portland to Chicago Midway.
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Find flight deals from Portland to Midway

Cheapest flights from Portland to Midway
Explore the most affordable flight options available from Portland to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 10, 2025.

This Southwest deal was found by Cheapflights users on 2/10. 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.
Mon 3/315:30 pmPWM - MDW
1 stop6h 45mSouthwest
Thu 4/34:45 pmMDW - PWM
1 stop6h 20mSouthwest
Deal found 2/10$258
This Delta deal was found by Cheapflights users on 2/10. 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.
Thu 3/66:00 amPWM - MDW
2 stops8h 05mDelta
Mon 3/1012:51 pmMDW - PWM
2 stops9h 01mDelta
Deal found 2/10$289

Find flights from Portland to Midway within your budget

Customize your flight search to find flights from Portland to Midway 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 February 10, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandChicago

PWM - MDW

PWMMDW

Portland

Mon 3/31

5:30 pm-11:15 pm

1 stop6h 45m

Chicago Midway

Thu 4/3

4:45 pm-12:05 am

1 stop6h 20m

$258

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 4/2

7:00 am-12:36 pm

1 stop6h 36m

Chicago Midway

Sat 4/5

1:12 pm-11:59 pm

2 stops9h 47m

$274

PortlandChicago

PWM - MDW

PWMMDW

Portland

Mon 4/14

7:22 pm-4:08 pm

1 stop21h 46m

$66

PortlandChicago

PWM - MDW

PWMMDW

Portland

Mon 3/10

1:00 pm-5:50 pm

1 stop5h 50m

$109

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 4/26

1:00 pm-10:26 pm

2 stops10h 26m

$120

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

Compare providers for flights from Portland to Midway

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 Portland to Midway in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 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 Portland, Maine-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland, Maine-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub 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 Portland, Maine-Chicago Midway Airport 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 Portland to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Portland 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.

Travel insights for flights from Portland to Midway

Get recent, data-driven insights about flights from Portland to Midway including ideal travel times, pricing trends, and more.

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

Currently, April is the cheapest month in which you can book a flight from Portland, Maine to Chicago Midway Airport (average of $160). Flying from Portland, Maine to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 PWM to MDW?

Find hourly flight availability from Portland to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 10, 2025.

One of the essential ways to save on airfare from Portland, Maine to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 29% on airfare.

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 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 Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated February 10, 2025.
To help decide which airline to fly from Portland to Chicago, see what other customers have to say about Southwest, Delta and Frontier. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,509 reviews

Crew

8.7

Entertainment

7.6

Boarding

8.2

Food

7.1

Overall

8.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Southwest
8.1
Very good
4,509 reviews
Southwest
8.1
Very good
4,509 reviews

Crew

8.7

Entertainment

7.6

Boarding

8.2

Food

7.1

Overall

8.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Delta
8.0
Very good
8,348 reviews
Southwest
8.1
Very good
4,509 reviews

Crew

8.7

Entertainment

7.6

Boarding

8.2

Food

7.1

Overall

8.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Frontier
6.0
Okay
3,396 reviews
Southwest
8.1
Very good
4,509 reviews

Crew

8.7

Entertainment

7.6

Boarding

8.2

Food

7.1

Overall

8.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Related info for your journey

Find useful and relevant information for your journey from Portland to Midway. 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 from for flights from Portland to Chicago Midway?

    For a flight from Portland to Chicago Midway, you will be flying from Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 0 outbound flights to Chicago Midway per day. 2 airlines have flights to Chicago Midway from Portland on a regular basis.

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

    Southwest, at $258, was found to be the cheapest airline from Portland, Maine to Chicago Midway Airport. An alternate airline flying to your destination would be Delta.

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

    One-way options have recently been found by users for as low as $66 on Frontier. Other airlines that offer cheap prices include Southwest from $109 and Delta from $120 one-way.

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

    While on average a flight from Portland, Maine to Chicago Midway Airport is generally $506, our data shows the cheapest flight currently is $401. When looking at the most popular route, (Portland - Chicago Midway), you can expect to pay $217 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland to Midway 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 Portland, Maine to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Portland, Maine to Chicago Midway Airport (average of $160). Flying from Portland, Maine to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 2 airlines flying from Portland to Midway

Discover the top 2 airlines that operate flights from Portland to Midway. 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 February 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$201Average$457FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$295Average$390FlexibilityNo cancel feeOn-time63%
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