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$55+ 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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PWM
Jan 10 — Jan 171
Fri 1/10
Fri 1/17
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 January 5, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$309
(Delta)

One-way from

$55
(Frontier)
Provider with most accurate pricing for Chicago Midway-Portland flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Portland flights.
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From Chicago Midway to Portland
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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 January 5, 2025.

This Delta deal was found by Cheapflights users on 1/3. 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 2/29:34 amMDW - PWM
1 stop5h 32mDelta
Sun 2/98:15 amPWM - MDW
2 stops8h 54mDelta
Deal found 1/3$309
This Southwest deal was found by Cheapflights users on 1/3. 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.
Sun 2/27:35 amMDW - PWM
1 stop4h 15mSouthwest
Sun 2/95:35 amPWM - MDW
1 stop7h 15mSouthwest
Deal found 1/3$334
This Trip.com deal was found by Cheapflights users on 1/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/1412:33 pmMDW - PWM
1 stop19h 35mFrontier
Fri 2/218:35 pmPWM - MDW
1 stop27h 16mFrontier
Deal found 1/4$425

Find flights from Midway to Portland within your budget

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 5, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sun 2/2

9:34 am-4:06 pm

1 stop5h 32m

Portland

Sun 2/9

8:15 am-4:09 pm

2 stops8h 54m

$309

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 1/23

8:10 am-3:00 pm

1 stop5h 50m

Portland

Tue 1/28

1:05 pm-6:35 pm

1 stop6h 30m

$334

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 2/14

12:33 pm-9:08 am

1 stop19h 35m

Portland

Fri 2/21

8:35 pm-10:51 pm

1 stop27h 16m

$425

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 2/3

11:33 am-8:12 pm

1 stop7h 39m

$55

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sun 2/2

9:34 am-4:06 pm

1 stop5h 32m

$115

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 2/14

6:25 am-2:05 pm

1 stop6h 40m

$150

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

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
eDreamsPrice 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.

Travel insights for flights from Midway to Portland

Get recent, data-driven insights about flights from Midway to Portland including ideal travel times, pricing trends, and more.

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 January 5, 2025.
Southwest
8.1
Very good
4,671 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,671 reviews
Southwest
8.1
Very good
4,671 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,517 reviews
Southwest
8.1
Very good
4,671 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,445 reviews
Southwest
8.1
Very good
4,671 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $309. Additional round-trip tickets that might be worth considering are offered by Southwest and Frontier, with the lowest prices starting at $334 and $425, respectively.

  • 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 Frontier ($55), Delta ($115), and Southwest ($150).

  • 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 April is currently the most expensive (average of $498). 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.

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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 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$196Average$342FlexibilityNo cancel feeOn-timeN/A
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