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$115+ 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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PWM
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap 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 January 27, 2026.

This Southwest deal was found by Cheapflights users on 1/25. 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 4/186:10 am
MDW
-
PWM
1 stop4h 45m
Southwest
Sat 4/254:35 pm
PWM
-
MDW
1 stop5h 05m
Southwest
Deal found 1/25$224
This Delta deal was found by Cheapflights users on 1/26. 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 4/159:27 am
MDW
-
PWM
1 stop5h 30m
Delta
Fri 4/2412:46 pm
PWM
-
MDW
1 stop6h 12m
Delta
Deal found 1/26$229
This Delta deal was found by Cheapflights users on 1/26. 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 4/159:27 am
MDW
-
PWM
1 stop5h 30m
Delta
Sat 4/256:30 am
PWM
-
MDW
2 stops10h 59m
Delta
Deal found 1/26$234
This Southwest deal was found by Cheapflights users on 1/25. 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.
Wed 2/256:50 am
MDW
-
PWM
1 stop4h 20m
Southwest
Sat 2/284:30 pm
PWM
-
MDW
1 stop6h 20m
Southwest
Deal found 1/25$266
This Delta deal was found by Cheapflights users on 1/26. 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 9/56:00 am
MDW
-
PWM
1 stop5h 22m
Delta
Sat 9/1211:25 am
PWM
-
MDW
2 stops8h 06m
Delta
Deal found 1/26$274
This Delta deal was found by Cheapflights users on 1/26. 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.
Sun 4/199:27 am
MDW
-
PWM
1 stop5h 30m
Delta
Fri 4/2412:46 pm
PWM
-
MDW
1 stop6h 12m
Delta
Deal found 1/26$284
This Delta deal was found by Cheapflights users on 1/25. 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 2/1812:45 pm
MDW
-
PWM
2 stops10h 33m
Delta
Wed 2/252:35 pm
PWM
-
MDW
2 stops8h 56m
Delta
Deal found 1/25$285
This Southwest deal was found by Cheapflights users on 1/25. 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 3/56:35 am
MDW
-
PWM
1 stop6h 40m
Southwest
Mon 3/95:30 pm
PWM
-
MDW
1 stop7h 05m
Southwest
Deal found 1/25$288
This Delta deal was found by Cheapflights users on 1/25. 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 4/159:27 am
MDW
-
PWM
1 stop5h 30m
Delta
Tue 4/215:21 am
PWM
-
MDW
2 stops8h 22m
Delta
Deal found 1/25$289

Find 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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$224
(Southwest)

One-way from

$115
(Delta)

Popular in

April

Cheapest in

March

Average price

$398
Provider with most accurate pricing for Chicago Midway-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Portland flights.
Search Deals
From Chicago Midway to Portland
Search Deals
One-way flight from Chicago Midway to Portland
Search Deals
High demand for flights, 1% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 27, 2026.
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

Sat 4/18

6:10 am-11:55 am

1 stop4h 45m

Portland

Sat 4/25

4:35 pm-8:40 pm

1 stop5h 05m

$224

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 4/15

9:27 am-3:57 pm

1 stop5h 30m

Portland

Wed 4/22

12:46 pm-5:58 pm

1 stop6h 12m

$229

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 4/3

9:35 am-4:06 pm

1 stop5h 31m

Portland

Tue 4/7

6:03 am-12:29 pm

2 stops7h 26m

$234

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 2/25

6:50 am-12:10 pm

1 stop4h 20m

Portland

Sat 2/28

4:30 pm-9:50 pm

1 stop6h 20m

$266

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 5/28

9:30 am-4:15 pm

1 stop5h 45m

Portland

Sat 5/30

11:25 am-6:31 pm

2 stops8h 06m

$289

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 4/15

1:00 pm-10:20 pm

1 stop8h 20m

Portland

Tue 4/21

3:55 pm-7:30 pm

1 stop4h 35m

$300

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 5/1

2:10 pm-11:25 pm

2 stops8h 15m

Portland

Mon 5/4

2:50 pm-10:45 pm

2 stops8h 55m

$317

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 6/11

7:15 am-2:30 pm

1 stop6h 15m

Portland

Tue 6/16

1:05 pm-5:55 pm

1 stop5h 50m

$317

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 3/12

9:35 am-4:06 pm

1 stop5h 31m

Portland

Sat 3/21

12:51 pm-5:54 pm

1 stop6h 03m

$320

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 4/15

1:00 pm-10:20 pm

1 stop8h 20m

Portland

Wed 4/22

6:10 am-10:40 am

1 stop5h 30m

$322

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

Showing 1-10 of 19 results
1
2

Compare providers for flights from Midway to Portland

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 Midway to Portland in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*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 Chicago Midway Airport-Portland, Maine flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Portland, Maine flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Portland, Maine flights, Cheapflights users trust FlightHub the most. FlightHub 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 Chicago Midway Airport-Portland, Maine 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 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, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland, Maine (average of $92). Flying from Chicago Midway Airport to Portland, Maine in April is currently the most expensive (average of $188). 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 January 27, 2026.

It’s typically best to fly out from Chicago Midway Airport to Portland, Maine in the afternoon. Doing so could potentially save you 55% on the flight price compared to flying in the evening, 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 January 27, 2026.
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
4,268 reviews

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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 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 4h 45m. The time it takes to get you to your destination can typically vary by up to 45m. 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 $259.

  • 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, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland, Maine (average of $92). Flying from Chicago Midway Airport to Portland, Maine in April is currently the most expensive (average of $188). 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
North Conway
Brunswick
Auburn
Conway

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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$259Average$460FlexibilityNo cancel feeOn-time63%

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