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Midway

$115+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
Jan 13 — Jan 201
Tue 1/13
Tue 1/20
1 adult, Economy
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Cheap 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 December 14, 2025.

This Southwest deal was found by Cheapflights users on 12/12. 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.
Sun 12/215:30 amPWM - MDW
1 stop4h 30mSouthwest
Tue 12/235:25 pmMDW - PWM
2 stops5h 40mSouthwest
Deal found 12/12$419
This Southwest deal was found by Cheapflights users on 12/12. 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.
Sat 12/135:40 amPWM - MDW
1 stop7h 45mSouthwest
Sun 12/149:35 amMDW - PWM
1 stop6h 15mSouthwest
Deal found 12/12$449
This Southwest deal was found by Cheapflights users on 12/12. 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 12/195:30 amPWM - MDW
1 stop4h 30mSouthwest
Sun 12/215:50 pmMDW - PWM
1 stop5h 15mSouthwest
Deal found 12/12$539
This Delta deal was found by Cheapflights users on 12/14. 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 12/2012:56 pmPWM - MDW
1 stop5h 30mDelta
Fri 12/269:29 amMDW - PWM
1 stop5h 39mDelta
Deal found 12/14$684
This Delta deal was found by Cheapflights users on 12/12. 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 12/2012:56 pmPWM - MDW
1 stop5h 30mDelta
Sun 12/289:29 amMDW - PWM
1 stop5h 39mDelta
Deal found 12/12$709

Find 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 December 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$274
(Southwest)

One-way from

$115
(Delta)

Popular in

April

Cheapest in

September

Average price

$253
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.
Search Deals
From Portland to Chicago Midway
Search Deals
One-way flight from Portland to Chicago Midway
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
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 December 14, 2025.
Use the filters below to find and compare flights from Portland to Chicago Midway Airport that are best for you.

Fly from

Portland

Fly to

Midway

Route

Depart

Return

Price

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sun 2/1

1:00 pm-5:35 pm

1 stop5h 35m

Chicago Midway

Sun 2/8

6:50 am-2:55 pm

1 stop7h 05m

$274

PortlandChicago

PWM - MDW

PWMMDW

Portland

Mon 1/5

12:20 pm-5:34 pm

1 stop6h 14m

Chicago Midway

Fri 1/9

9:32 am-10:27 pm

2 stops11h 55m

$284

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 1/31

2:35 pm-10:22 pm

2 stops8h 47m

Chicago Midway

Sat 2/7

1:26 pm-10:27 pm

2 stops8h 01m

$284

PortlandChicago

PWM - MDW

PWMMDW

Portland

Mon 4/13

5:30 am-12:05 pm

1 stop7h 35m

Chicago Midway

Wed 4/15

9:10 am-3:20 pm

1 stop5h 10m

$294

PortlandChicago

PWM - MDW

PWMMDW

Portland

Mon 1/26

3:30 pm-10:05 pm

2 stops7h 35m

Chicago Midway

Thu 1/29

9:50 am-2:55 pm

1 stop4h 05m

$299

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 1/31

6:18 pm-11:45 am

2 stops18h 27m

Chicago Midway

Sun 2/8

1:00 pm-9:07 am

1 stop19h 07m

$310

PortlandChicago

PWM - MDW

PWMMDW

Portland

Mon 1/5

3:00 pm-8:30 pm

2 stops6h 30m

Chicago Midway

Fri 1/9

6:50 am-12:10 pm

1 stop4h 20m

$324

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 1/2

5:30 am-10:25 am

1 stop5h 55m

Chicago Midway

Sun 1/4

5:30 am-11:10 am

1 stop4h 40m

$324

PortlandChicago

PWM - MDW

PWMMDW

Portland

Mon 1/26

12:20 pm-5:55 pm

1 stop6h 35m

Chicago Midway

Tue 1/27

12:48 pm-11:22 pm

2 stops9h 34m

$325

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 1/13

5:45 am-11:35 am

1 stop6h 50m

Chicago Midway

Fri 1/16

7:05 am-3:15 pm

1 stop7h 10m

$339

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/12

Showing 1-10 of 16 results
1
2

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Expedia the most. Expedia 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.

Cheapflights Insights

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

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

Currently, June is the cheapest month in which you can book a flight from Portland, Maine to Chicago Midway Airport (average of $97). Flying from Portland, Maine to Chicago Midway Airport in April is currently the most expensive (average of $176). 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 December 14, 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 in the morning could potentially save you up to 14% on airfare.

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 December 14, 2025.
See what other customers who have flown with Southwest and Delta from Portland to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,251 reviews

Boarding

8.1

Overall

7.9

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

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
4,251 reviews
Southwest
7.9
Good
4,251 reviews

Boarding

8.1

Overall

7.9

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

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
Delta
7.9
Good
8,007 reviews
Southwest
7.9
Good
4,251 reviews

Boarding

8.1

Overall

7.9

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

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 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.

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

    Airlines like Southwest and Delta fly from Portland, Maine to Chicago Midway Airport in about 5h 35m. The time it takes to get you to your destination can typically vary by up to 39m. Airlines will cover a distance of 892 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Southwest, at $246, was found to be the cheapest airline from Portland, Maine to Chicago Midway Airport. An alternate airline flying to your destination would be Delta.

  • 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, June is the cheapest month in which you can book a flight from Portland, Maine to Chicago Midway Airport (average of $97). Flying from Portland, Maine to Chicago Midway Airport in April is currently the most expensive (average of $176). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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 December 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$246Average$397FlexibilityNo cancel feeOn-time63%
DeltaCheapest$253Average$327FlexibilityNo cancel feeOn-timeN/A

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