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$90+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PWM
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
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 June 18, 2025.

Round-trip from

$234
(Delta)

One-way from

$90
(Southwest)

Popular in

July

Cheapest in

September

Average price

$411

Good round-trip deal

$259 or less

Good one-way deal

$185 or less
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. 5% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 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 Chicago Midway to Portland.
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Price to beat on a one-way flight from Chicago Midway to Portland.
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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 June 18, 2025.

This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/316:00 amMDW - PWM
1 stop5h 29mDelta
Sat 9/611:48 amPWM - MDW
1 stop6h 49mDelta
Deal found 6/16$234
This Southwest deal was found by Cheapflights users on 6/16. 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.
Tue 9/211:40 amMDW - PWM
Nonstop2h 15mSouthwest
Sat 9/65:45 amPWM - MDW
1 stop6h 25mSouthwest
Deal found 6/16$241

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 June 18, 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

Sun 8/31

6:00 am-12:29 pm

1 stop5h 29m

Portland

Sat 9/6

11:48 am-5:37 pm

1 stop6h 49m

$234

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 9/2

11:40 am-2:55 pm

Nonstop2h 15m

Portland

Sat 9/6

5:45 am-11:10 am

1 stop6h 25m

$241

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sun 8/31

5:55 pm-9:15 pm

Nonstop2h 20m

$90

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 10/31

6:00 am-1:35 pm

1 stop6h 35m

$109

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 6/27

9:12 pm-6:30 pm

1 stop20h 18m

$111

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 7/17

8:14 pm-12:15 pm

3 stops39h 01m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

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 June 18, 2025.

It’s typically best to fly out from Chicago Midway Airport to Portland, Maine at noon. Doing so could potentially save you 24% on the flight price compared to flying in the afternoon, which is usually more expensive.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, Maine, 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 68.0 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 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 June 18, 2025.
Read reviews from past customers who have flown Southwest, Delta and Frontier from Chicago to Portland. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,964 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,301 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • What are the cheapest airlines flying from Chicago Midway Airport to Portland, Maine round-trip?

    Flying on Delta is currently your cheapest option to Portland, Maine, with prices starting at $234. Another option worth looking into is Southwest, starting at $241 round trip. You may be able to fly from Chicago Midway Airport to Portland, Maine for 39% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Portland, Maine one-way?

    The cheapest airlines for a one-way flight from Chicago Midway Airport to Portland, Maine are Southwest ($90), Delta ($109), and Frontier ($111).

  • What are the cheapest flights from Chicago Midway Airport to Portland, Maine?

    Looking for the cheapest flight from Chicago Midway Airport to Portland, Maine? While on average our users pay $277, our data indicates the cheapest price to be $129. The most popular route (Chicago Midway - Portland), is priced around $205.

  • 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
North Conway
Bath
Brunswick
Auburn
Conway
Lewiston

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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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$191Average$401FlexibilityNo cancel feeOn-time63%

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