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Midway

$100+ 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
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$239
(Southwest)

One-way from

$100
(Southwest)

Popular in

December

Cheapest in

September

Average price

$339

Good round-trip deal

$229 or less

Good one-way deal

$208 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. 11% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 14, 2025.

This Southwest deal was found by Cheapflights users on 8/13. 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 10/3110:25 amPWM - MDW
Nonstop2h 35mSouthwest
Sun 11/25:05 amMDW - PWM
1 stop5h 05mSouthwest
Deal found 8/13$239
This Southwest deal was found by Cheapflights users on 8/13. 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.
Tue 9/235:50 amPWM - MDW
1 stop6h 55mSouthwest
Tue 9/232:55 pmMDW - PWM
1 stop6h 30mSouthwest
Deal found 8/13$251
This Southwest deal was found by Cheapflights users on 8/13. 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 8/304:50 pmPWM - MDW
Nonstop2h 35mSouthwest
Sun 8/315:55 pmMDW - PWM
Nonstop2h 20mSouthwest
Deal found 8/13$253
This Delta deal was found by Cheapflights users on 8/13. 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.
Wed 8/276:00 amPWM - MDW
2 stops7h 28mDelta
Sun 8/316:00 amMDW - PWM
1 stop5h 29mDelta
Deal found 8/13$254
This Southwest deal was found by Cheapflights users on 8/13. 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 11/14:45 pmPWM - MDW
Nonstop2h 35mSouthwest
Sun 11/25:05 amMDW - PWM
1 stop5h 05mSouthwest
Deal found 8/13$255
This Southwest deal was found by Cheapflights users on 8/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2810:35 amPWM - MDW
Nonstop2h 30mSouthwest
Tue 9/211:40 amMDW - PWM
Nonstop2h 15mSouthwest
Deal found 8/14$259
This Southwest deal was found by Cheapflights users on 8/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/94:55 pmPWM - MDW
1 stop6h 30mSouthwest
Wed 9/102:55 pmMDW - PWM
1 stop6h 30mSouthwest
Deal found 8/14$261
This Southwest deal was found by Cheapflights users on 8/13. 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 9/255:40 pmPWM - MDW
1 stop4h 55mSouthwest
Sun 9/287:10 pmMDW - PWM
Nonstop2h 15mSouthwest
Deal found 8/13$269
This Delta deal was found by Cheapflights users on 8/13. 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.
Wed 8/276:00 amPWM - MDW
2 stops7h 28mDelta
Wed 9/34:25 pmMDW - PWM
1 stop6h 38mDelta
Deal found 8/13$270

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 August 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

Fri 10/31

10:25 am-12:00 pm

Nonstop2h 35m

Chicago Midway

Sun 11/2

5:05 am-11:10 am

1 stop5h 05m

$239

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 9/23

5:50 am-11:45 am

1 stop6h 55m

Chicago Midway

Tue 9/23

2:55 pm-10:25 pm

1 stop6h 30m

$251

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 8/30

4:50 pm-6:25 pm

Nonstop2h 35m

Chicago Midway

Sun 8/31

5:55 pm-9:15 pm

Nonstop2h 20m

$253

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 8/27

6:00 am-12:28 pm

2 stops7h 28m

Chicago Midway

Sun 8/31

6:00 am-12:29 pm

1 stop5h 29m

$254

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 11/1

4:45 pm-6:20 pm

Nonstop2h 35m

Chicago Midway

Sun 11/2

5:05 am-11:10 am

1 stop5h 05m

$255

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 8/28

10:35 am-12:05 pm

Nonstop2h 30m

Chicago Midway

Tue 9/2

11:40 am-2:55 pm

Nonstop2h 15m

$259

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 9/25

10:35 am-12:05 pm

Nonstop2h 30m

Chicago Midway

Sun 9/28

7:10 pm-10:25 pm

Nonstop2h 15m

$259

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 9/9

4:55 pm-10:25 pm

1 stop6h 30m

Chicago Midway

Wed 9/10

2:55 pm-10:25 pm

1 stop6h 30m

$261

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 10/31

10:25 am-12:00 pm

Nonstop2h 35m

$100

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 10/31

12:45 pm-5:55 pm

1 stop6h 10m

$110

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 18 results
1
2

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 August 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 at noon 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 August 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
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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?

    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 $308, our data shows the cheapest flight currently is $125. When looking at the most popular route, (Portland - Chicago Midway), you can expect to pay $209 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$253Average$327FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$264Average$390FlexibilityNo cancel feeOn-time63%

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