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Midway

$110+ 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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
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 septiembre 17, 2025.

Round-trip from

$225
(Southwest)

One-way from

$110
(Southwest)

Popular in

December

Cheapest in

September

Average price

$281

Good round-trip deal

$393 or less

Good one-way deal

$203 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. 14% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 17, 2025.

This Southwest deal was found by Cheapflights users on 9/16. 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.
mié. 10/294:00 pmPWM - MDW
Nonstop2h 35mSouthwest
vie. 10/3112:50 pmMDW - PWM
Nonstop2h 10mSouthwest
Deal found 9/16$225
This Southwest deal was found by Cheapflights users on 9/15. 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.
sáb. 11/14:45 pmPWM - MDW
Nonstop2h 35mSouthwest
mar. 11/46:40 amMDW - PWM
1 stop4h 30mSouthwest
Deal found 9/15$241
This Southwest deal was found by Cheapflights users on 9/15. 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. 10/285:25 pmPWM - MDW
1 stop4h 25mSouthwest
vie. 10/3112:50 pmMDW - PWM
Nonstop2h 10mSouthwest
Deal found 9/15$244
This Southwest deal was found by Cheapflights users on 9/16. 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. 11/1812:45 pmPWM - MDW
1 stop6h 05mSouthwest
mié. 11/196:40 amMDW - PWM
1 stop7h 15mSouthwest
Deal found 9/16$251
This Delta deal was found by Cheapflights users on 9/15. 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.
mar. 10/2812:45 pmPWM - MDW
1 stop6h 40mDelta
vie. 10/311:08 pmMDW - PWM
2 stops9h 57mDelta
Deal found 9/15$259

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 septiembre 17, 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. 10/29

5:45 am-12:05 pm

2 stops7h 20m

Chicago Midway

vie. 10/31

12:50 pm-4:00 pm

Nonstop2h 10m

$240

PortlandChicago

PWM - MDW

PWMMDW

Portland

mar. 11/18

12:45 pm-5:50 pm

1 stop6h 05m

Chicago Midway

mié. 11/19

6:40 am-2:55 pm

1 stop7h 15m

$251

PortlandChicago

PWM - MDW

PWMMDW

Portland

sáb. 11/8

12:00 pm-10:14 pm

2 stops11h 14m

Chicago Midway

mié. 11/12

12:47 pm-11:54 pm

2 stops10h 07m

$261

PortlandChicago

PWM - MDW

PWMMDW

Portland

mar. 10/28

5:42 am-12:28 pm

2 stops7h 46m

Chicago Midway

vie. 10/31

1:08 pm-12:05 am

2 stops9h 57m

$264

PortlandChicago

PWM - MDW

PWMMDW

Portland

jue. 10/2

5:45 am-10:15 am

1 stop5h 30m

Chicago Midway

lun. 10/6

2:15 pm-9:20 pm

1 stop6h 05m

$299

PortlandChicago

PWM - MDW

PWMMDW

Portland

jue. 11/6

6:01 am-4:14 pm

2 stops11h 13m

Chicago Midway

mar. 11/11

1:14 pm-11:54 pm

2 stops9h 40m

$301

PortlandChicago

PWM - MDW

PWMMDW

Portland

jue. 10/23

5:42 am-12:28 pm

2 stops7h 46m

Chicago Midway

dom. 10/26

6:00 am-12:32 pm

1 stop5h 32m

$304

PortlandChicago

PWM - MDW

PWMMDW

Portland

dom. 11/23

5:25 pm-11:00 pm

1 stop6h 35m

Chicago Midway

mar. 11/25

5:35 am-11:10 am

1 stop4h 35m

$310

PortlandChicago

PWM - MDW

PWMMDW

Portland

mié. 9/24

5:50 am-11:45 am

1 stop6h 55m

Chicago Midway

mar. 9/30

11:40 am-2:55 pm

Nonstop2h 15m

$313

PortlandChicago

PWM - MDW

PWMMDW

Portland

vie. 10/31

5:25 am-1:00 pm

2 stops8h 35m

Chicago Midway

dom. 11/2

5:05 am-11:10 am

1 stop5h 05m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 21 results
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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 septiembre 17, 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 15% 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 septiembre 17, 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
8.0
Very good
4,242 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 7h 20m. The time it takes to get you to your destination can typically vary by up to 3h 54m. 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?

    Delta, at $253, was found to be the cheapest airline from Portland, Maine to Chicago Midway Airport. An alternate airline flying to your destination would be Southwest.

  • 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 $386, our data shows the cheapest flight currently is $129. When looking at the most popular route, (Portland - Chicago Midway), you can expect to pay $225 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 septiembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$253Average$327FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$264Average$397FlexibilityNo cancel feeOn-time63%

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