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$90+ 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 7/2. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$248
(Delta)

One-way from

$90
(Southwest)

Popular in

November

Cheapest in

September

Average price

$366

Good round-trip deal

$318 or less

Good one-way deal

$179 or less
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. 12% potential increase in price ($52 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Portland to Chicago Midway.
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Price to beat on a one-way 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 junio 12, 2025.

This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/212:49 pmPWM - MDW
1 stop6h 52mDelta
mié. 7/99:25 amMDW - PWM
1 stop5h 46mDelta
Deal found 6/11$248
This Southwest deal was found by Cheapflights users on 6/10. 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.
mar. 7/226:55 pmPWM - MDW
Nonstop2h 35mSouthwest
mar. 8/511:40 amMDW - PWM
Nonstop2h 15mSouthwest
Deal found 6/10$254
This CheapTicketsDeal deal was found by Cheapflights users on 6/9. 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 CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/1012:51 pmPWM - MDW
1 stop6h 49mAlaska Airlines
mar. 8/126:04 amMDW - PWM
1 stop5h 25mAlaska Airlines
Deal found 6/9$368
This Booking.com deal was found by Cheapflights users on 6/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/1012:05 pmPWM - MDW
1 stop23h 21mFrontier
dom. 10/128:39 amMDW - PWM
1 stop25h 26mFrontier
Deal found 6/10$392

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 junio 12, 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

mié. 7/2

12:49 pm-6:41 pm

1 stop6h 52m

Chicago Midway

mié. 7/9

9:25 am-4:11 pm

1 stop5h 46m

$248

PortlandChicago

PWM - MDW

PWMMDW

Portland

mar. 7/22

6:55 pm-8:30 pm

Nonstop2h 35m

Chicago Midway

mar. 8/5

11:40 am-2:55 pm

Nonstop2h 15m

$254

PortlandChicago

PWM - MDW

PWMMDW

Portland

dom. 8/10

12:51 pm-6:40 pm

1 stop6h 49m

Chicago Midway

mar. 8/12

6:04 am-12:29 pm

1 stop5h 25m

$368

PortlandChicago

PWM - MDW

PWMMDW

Portland

vie. 10/10

12:05 pm-10:26 am

1 stop23h 21m

Chicago Midway

dom. 10/12

8:39 am-11:05 am

1 stop25h 26m

$392

PortlandChicago

PWM - MDW

PWMMDW

Portland

mié. 7/2

6:55 pm-8:30 pm

Nonstop2h 35m

$90

PortlandChicago

PWM - MDW

PWMMDW

Portland

vie. 10/31

10:00 am-9:44 pm

2 stops12h 44m

$114

PortlandChicago

PWM - MDW

PWMMDW

Portland

sáb. 7/12

6:58 pm-3:06 pm

1 stop21h 08m

$141

PortlandChicago

PWM - MDW

PWMMDW

Portland

dom. 7/13

12:46 pm-9:41 am

2 stops21h 55m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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, 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 junio 12, 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 at noon tend to be the most expensive. A flight in the evening could potentially save you up to 9% 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 junio 12, 2025.
To help decide which airline to fly from Portland to Chicago, see what other customers have to say about Alaska Airlines, Southwest and Delta. 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Frontier
5.9
Fair
3,295 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 1 outbound flight 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?

    Delta, at $248, was found to be the cheapest airline from Portland, Maine to Chicago Midway Airport.Alternate airlines to your destination round-trip include Southwest and Alaska Airlines.

  • 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 $90 on Southwest. Other airlines that offer cheap prices include Delta from $114 and Frontier from $141 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 $298, our data shows the cheapest flight currently is $114. When looking at the most popular route, (Portland - Chicago Midway), you can expect to pay $254 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
Lansing
Benton Harbor
Porter
Hammond
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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$201Average$327FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$264Average$371FlexibilityNo cancel feeOn-time63%

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