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$76+ Cheap flights from Midway (MDW) to Portland, ME (PWM)

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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PWM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Midway to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Portland (PWM). 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 September 11, 2025.

Round-trip from

$242
(Southwest)

One-way from

$76
(Southwest)

Popular in

July

Cheapest in

November

Average price

$271
From Chicago Midway to Portland
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One-way flight from Chicago Midway to Portland
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Highest demand for flights based on searches. 10% potential increase in price ($44 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 September 2025
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Find flight deals from Midway to Portland

Cheapest flights from Midway to Portland
Explore the most affordable flight options available from Midway to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2010:55 amMDW - PWM
Nonstop2h 10mSouthwest
Thu 10/232:40 pmPWM - MDW
Nonstop2h 35mSouthwest
Deal found 9/9$242
This Delta deal was found by Cheapflights users on 9/10. 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.
Fri 12/59:34 amMDW - PWM
1 stop5h 32mDelta
Mon 12/82:34 pmPWM - MDW
2 stops9h 58mDelta
Deal found 9/10$250
This Delta deal was found by Cheapflights users on 9/10. 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.
Mon 11/106:00 amMDW - PWM
1 stop5h 30mDelta
Tue 11/186:00 amPWM - MDW
1 stop6h 52mDelta
Deal found 9/10$258
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2810:05 amMDW - PWM
2 stops8h 50mSouthwest
Sat 11/110:45 amPWM - MDW
2 stops7h 15mSouthwest
Deal found 9/11$259
This Delta deal was found by Cheapflights users on 9/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/249:35 amMDW - PWM
1 stop5h 28mDelta
Wed 10/2912:45 pmPWM - MDW
1 stop6h 40mDelta
Deal found 9/9$278
This Delta deal was found by Cheapflights users on 9/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2012:48 pmMDW - PWM
2 stops10h 17mDelta
Thu 10/2312:45 pmPWM - MDW
1 stop6h 40mDelta
Deal found 9/9$283
This Delta deal was found by Cheapflights users on 9/11. 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.
Fri 9/2612:43 pmMDW - PWM
2 stops10h 51mDelta
Wed 10/112:40 pmPWM - MDW
1 stop6h 55mDelta
Deal found 9/11$287
This Delta deal was found by Cheapflights users on 9/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/271:08 pmMDW - PWM
2 stops9h 57mDelta
Thu 10/305:42 amPWM - MDW
2 stops7h 46mDelta
Deal found 9/9$288
This Southwest deal was found by Cheapflights users on 9/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/258:20 amMDW - PWM
2 stops10h 45mSouthwest
Tue 10/285:45 amPWM - MDW
2 stops7h 20mSouthwest
Deal found 9/9$296

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Portland 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 September 11, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Portland that are best for you.

Fly from

Midway

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 10/20

10:55 am-2:05 pm

Nonstop2h 10m

Portland

Thu 10/23

2:40 pm-4:15 pm

Nonstop2h 35m

$242

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 10/28

10:05 am-7:55 pm

2 stops8h 50m

Portland

Sat 11/1

10:45 am-5:00 pm

2 stops7h 15m

$259

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 3/3

1:05 pm-9:59 pm

1 stop7h 54m

Portland

Wed 3/4

6:00 am-12:35 pm

2 stops7h 35m

$263

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 10/20

12:48 pm-12:05 am

2 stops10h 17m

Portland

Thu 10/23

12:45 pm-6:25 pm

1 stop6h 40m

$283

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 9/26

12:43 pm-12:34 am

2 stops10h 51m

Portland

Wed 10/1

12:40 pm-6:35 pm

1 stop6h 55m

$287

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 10/27

1:08 pm-12:05 am

2 stops9h 57m

Portland

Thu 10/30

5:42 am-12:28 pm

2 stops7h 46m

$288

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sat 10/25

8:20 am-8:05 pm

2 stops10h 45m

Portland

Tue 10/28

5:45 am-12:05 pm

2 stops7h 20m

$296

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 10/22

12:30 pm-7:55 pm

1 stop6h 25m

$76

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 10/21

12:30 pm-7:55 pm

1 stop6h 25m

$76

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 1/14

2:20 pm-10:15 pm

2 stops6h 55m

$93

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 19 results
1
2

Best time to book a flight from Midway to Portland

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

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

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland, Maine (average of $296). Flying from Chicago Midway Airport to Portland, Maine in July is currently the most expensive (average of $394). 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 MDW to PWM?

Find hourly flight availability from Midway to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

It’s typically best to fly out from Chicago Midway Airport to Portland, Maine at noon. Doing so could potentially save you 10% on the flight price compared to flying in the morning, which is usually more expensive.

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated September 11, 2025.
Get a feel of what it's like to fly with Southwest from Chicago Midway Airport to Portland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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 Midway to Portland. 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 into for flights to Portland from Chicago Midway?

    For a flight from Chicago Midway to Portland, you will be flying into Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 0 inbound flights from Chicago Midway per day. 1 airline has flights to Portland from Chicago Midway on a regular basis.

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

    Airlines like Southwest and Delta fly from Chicago Midway Airport to Portland, Maine in about 2h 10m. The time it takes to get you to your destination can typically vary by up to 5h 44m. The distance between Chicago Midway Airport and Portland, Maine is about 892 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What is the cheapest airline to fly from Chicago Midway Airport to Portland, Maine round-trip?

    Flying on Southwest is currently your cheapest option to Portland, Maine, with prices starting at $276. You may be able to fly from Chicago Midway Airport to Portland, Maine for 31% less than the average price by searching for this airline.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland, Maine (average of $296). Flying from Chicago Midway Airport to Portland, Maine in July is currently the most expensive (average of $394). 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
Brunswick
North Conway
Auburn
Conway
Lewiston

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Midway to Portland

Discover the top airline that operate flights from Midway to Portland. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$276Average$411FlexibilityNo cancel feeOn-time63%

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